Chemicals >> Oxidizing Agents > Peroxides

Hydrogen peroxide

Name Reactions

Follow-up reaction of Brown Hydroboration

Recent Literature

An efficient bismuth tribromide catalyzed oxidation of various alcohols with aqueous hydrogen peroxide provides carbonyl compounds in good yields.
M.-k. Han, S. Kim, S. T. Kim, J. C. Lee, Synlett, 2015, 26, 2434-2436.

CeBr₃/H₂O₂ is a very efficient system for the green oxidation of secondary and benzylic alcohols to carbonyls. The mechanism involves the generation of a reactive brominating species (RBS) with high oxidation selectivity of secondary over primary alcohols.
C. He, F. Ma, W. Zhang, R. Tong, Org. Lett., 2022, 24, 3499-3503.

Cost-effective and widely applicable protocols for controlled and predictably selective oxidation of methyl-/alkylarenes to corresponding value-added carbonyls have been developed, using a surfactant-based oxodiperoxo molybdenum catalyst in water and hydrogen peroxide (H₂O₂) as an environmentally benign green oxidant without any external base, additive, or cocatalyst.
P. Thiruvengetam, D. K. Chand, J. Org. Chem., 2022, 87, 4061-4077.

Pd⁰/C exhibited excellent catalytic activity in the oxidation of styrene derivatives to corresponding ketones with hydrogen peroxide as oxidant. This modified Wacker oxidation is cost-efficient and environmentally friendly and avoids the use of a copper salt as a co-catalyst.
X. Xia, X. Gao, J. Xu, C. Hu, X. Peng, Synlett, 2017, 28, 607-610.

Catalyzed by Se/Fe via hybrid mechanisms, the carbon-carbon double bond in alkenes can break to produce carbonyls under mild conditions. Since O₂ can be used as a partial oxidant, the employed H₂O₂ amount can be lowered to avoid peroxide residues, making the process even safer for operation.
X. Li, H. Hua, Y. Liu, L. Yu, Org. Lett., 2023, 25, 6720-6724.

For a selective oxidation of olefins, in particular, aromatic olefins to carbonyls, stoichiometric toxic oxidants or a high-cost catalyst is required. A practical light-enabled oxidation of olefins using H₂O₂ as a clean and low-toxic oxidant provides a broad scope of carbonyls in high yield without catalyst.
W. Yu, Z. Zhao, Org. Lett., 2019, 21, 7713-7716.

A clean and safe method for the dihydroxylation of alkenes under organic-solvent- and metal-free conditions was developed. The resin-supported sulfonic acid is easily recycled.
Y. Usui, K. Sato, M. Tanaka, Angew. Chem. Int. Ed., 2003, 42, 5623-5625.

Os(VI) can be recycled to Os(VIII) by a coupled electron-transfer-mediator system based on N-methylmorpholine and a biomimetic flavin, leading to a mild and selective electron transfer. Aliphatic, aromatic, and functionalized olefins were successfully cis-dihydroxylated. The present biomimetic catalytic system also works well in Sharpless asymmetric dihydroxylation.
S. Y. Jonsson, K. Färnegårdh, J.-E. Bäckvall, J. Am. Chem. Soc., 2001, 123, 1365-1371.

As the highly volatile OsO₄ is quite toxic, the development of alternative catalysts for cis-1,2-dihydroxylation of alkenes is needed. A complex of a nitrogen-based tetradentate ligand, tris(2-pyridylmethyl)amine (tpa), and osmium acts as a very efficient turnover catalyst for syn-selective dihydroxylation of various alkenes in aqueous media using hydrogen peroxide as oxidant.
H. Sugimoto, K. Kitayama, S. Mori, S. Itho, J. Am. Chem. Soc., 2012, 134, 19270-19280.

Convenient methods for the preparation of stable and non-volatile mono- and dichloroborane adducts of dioxane from dioxane-BCl₃ and NaBH₄ in the presence of catalytic amounts of tri- or tetraglyme were developed. The dioxane-monochloroborane adduct hydroborates representative olefins cleanly and rapidly and lead to the corresponding alcohols in quantitative yields after oxidation.
J. V. B. Kanth, H. C. Brown, J. Org. Chem, 2001, 66, 5359-5365.

A rhodium-catalyzed enantioselective syn addition of bis(catecholato)diboron to simple alkenes in the presence of (S)-Quinap provides enantioenriched 1,2-diols after subsequent oxidation. The substrate scope, the reaction mechanism, and competing pathways are discussed.
S. Trudeau, J. M. Morgan, M. Shrestha, J. P. Morken, J. Org. Chem., 2005, 70, 9538-9544.

A Mo-catalyzed anti-dihydroxylation of secondary allylic alcohols provides 1,2,3-triols bearing up to three continuous stereocenters with excellent diastereocontrol. The excellent diastereomeric ratios of the final triol products can be achieved due to the high level of both diastereocontrol in the initial epoxidation and regiocontrol in the following hydrolysis in situ.
S. Su, C. Wang, Org. Lett., 2019, 21, 2436-2440.

A reductive coupling of terminal alkynes with α-chloro boronic esters affords allylic alcohols with excellent regioselectivity (anti-Markovnikov) and an E/Z ratio greater than 200:1. The reaction can be performed in the presence of a wide range of functional groups, is stereospecific, and allows for the robust and highly selective synthesis of chiral allylic alcohols.
A. B. Shaff, L. Yang, M. T. Lee, G. Lalic, J. Am. Chem. Soc., 2023, 145, 24615-24624.

Pt-catalyzed enantioselective addition of bis(pinacolato)diboron (B₂(pin)₂) to conjugated dienes enables an asymmetric 1,4-dihydroxylation of 1,3-dienes. Dienes which are unable to adopt the S-cis conformation are unreactive. For most substrates, 1,4-addition is the predominant pathway.
H. E. Burks, L. T. Kliman, J. P. Morken, J. Am. Chem. Soc., 2009, 131, 9134-9135.

A catalytic stereoselective 1,4-diboration of conjugated dienes with B₂(pin)₂ and the presence of Ni(cod)₂ and PCy₃ as the catalyst roceeds efficiently at low catalyst loadings and broadens the substrate scope of current methods for catalytic diene diboration by including internal and sterically hindered. The intermediate allylboronate was oxidized to the stereodefined allylic 1,4-diol.
R. J. Ely, J. P. Morken, Org. Lett., 2010, 12, 4348-4351.

An enantioselective nickel-catalyzed borylative coupling of 1,3-dienes with aldehydes provides an efficient route to highly valuable homoallylic alcohols in a single step. Enabled by a chiral spiro phosphine-oxazoline nickel complex, this transformation yields products with exceptional diastereoselectivity, E-selectivity, and enantioselectivity.
J.-T. Ma, T. Zhang, B.-Y. Yao, L.-J. Xiao, Q.-L. Zhou, J. Am. Chem. Soc., 2023, 145, 19195-19201.

Cu-catalyzed highly regio- and stereoselective 1,4-protoboration of dienylboronates provides unsymmetrical 1,4-bifunctional allylboron reagents. A subsequent chemoselective allylboration with aldehydes followed by oxidative workup give diol products with high diastereoselectivity.
S. Gao, M. Wang, M. Chen, Org. Lett., 2018, 20, 7921-7925.

An oxidative alkyne translocation of readily accessible homopropargylic alcohols provides unsymmetrical but-2-yne-1,4-diones in good yields via an unprecedented one-pot sequential electro-oxidative annulation-fragmentation-chemical selenoxide elimination process. Excellent functional group compatibility was observed.
A. Halder, D. Maiti, J. Dutta, S. D. Sarkar, Org. Lett., 2023, 25, 7578-7583.

Hydrogen peroxide as an eco-friendly oxidant provides hydroxylation products of arylboronic acids in an efficient manner under metal- and base-free aerobic in the presence of a room-temperature ionic liquid (RTIL).
E.-J. Shin, G.-T. Kown, S.-H. Kim, Synlett, 2019, 30, 1815-1819.

The use of aqueous hydrogen peroxide as oxidizing agent and molecular iodine as catalyst enables a mild and efficient methodology for the ipso-hydroxylation of arylboronic acids to phenols. The reactions were performed at room temperature in short reaction time under metal-, ligand- and base-free conditions.
A. Gogoi, U. Bora, Synlett, 2012, 23, 1079-1081.

Rapid, efficient methods enable the preparation of phenols from the oxidation of arylhydrosilanes. Electron-rich aromatics benefit from silane activation via oxidation to the methoxysilane using homogeneous or heterogeneous transition metal catalysis. A combination of these two oxidations into a streamlined flow procedure involves minimal processing of reaction intermediates.
E. J. Rayment, N. Summerhill, E. A. Anderson, J. Org. Chem., 2012, 77, 7052-7060.

A bifunctional bidentate carboxyl-pyridone ligand enables a room-temperature Pd-catalyzed C-H hydroxylation of a broad range of benzoic and phenylacetic acids with aqueous hydrogen peroxide. The scalability of this methodology is demonstrated by a 1 mol scale reaction of ibuprofen using only a 1 mol % Pd catalyst loading.
Z. Li, H. S. Park, J. X. Qiao, K.-S. Yeung, J.-Q. Yu, J. Am. Chem. Soc., 2022, 144, 18109-18116.

The combination of sBuLi and TMEDA in CPME at -60 °C enables deprotonation of unactivated, chiral secondary dialkyl TIB esters. These carbanions were reacted with a range of neopentyl boronic esters which, after 1,2-metalate rearrangement and oxidation, gave a range of tertiary alcohols in high yield and high ee. Further functional group transformations of the tertiary boronic esters were demonstrated.
A. P. Pulis, D. J. Blair, E. Torres, V. K. Aggarwal, J. Am. Chem. Soc., 2013, 135, 16054-16057.

Lithiated epoxides react stereospecifically with boronates to give syn-1,2-diols, a process that can be used iteratively to create triols containing four stereogenic centers.
E. Vedrenne, O. A. Wallner, M. Vitale, F. Schmidt, V. K. Aggarwal, Org. Lett., 2009, 11, 165-168.

A direct, mild ketohydroxylation of various 1-aryl-1-alkenes with H₂O₂, catalyzed by the inexpensive 12-tungstophosphoric acid/cetylpyridinium chloride system, gave acyloins in good yields and high regioselectivies.
Y. Zhang, Z. Shen, J. Tang, Y. Zhang, L. Kong, Y. Zhang, Org. Biomol. Chem., 2006, 4, 1478-1482.

Diphenyl diselenide catalyzes an oxidative degradation of benzoins to benzoic acids under mild conditions.
H. Cao, T. Chen, C. Yang, J. Ye, X. Zhang, Synlett, 2019, 30, 1683-1687.

Benzyl chlorides and bromides can be directly oxidized to the corresponding benzoic acids in an eco-safer way using 30% hydrogen peroxide with Na₂WO₄ * 2H₂O as a catalyst and [CH₃(n-C₈H₁₇)₃N]⁺HSO₄ as a phase-transfer agent (PTC) without any organic solvents.
M. Shi, Y.-S. Feng, J. Org. Chem., 2001, 66, 3235-3237.

A cooperative primary amine and ketone dual catalytic approach enables the asymmetric α-hydroxylation of β-ketocarbonyls with H₂O₂ in excellent yield and enantioselectivity. Notably, late-stage hydroxylation for peptidyl amide or chiral esters can also be achieved with high stereoselectivity.
M. Cai, K. Xu, Y. Li, Z. Nie, L. Zhang, S. Luo, J. Am. Chem. Soc., 2021, 143, 1078-1087.

Trifluoroacetone catalyzes a mild and operationally simple epoxidation of various alkens in good yields using hydrogen peroxide as primary oxidant at high pH. The use of H₂O₂ as oxidant significantly reduces the amount of solvent and salts introduced.
L. Shu, Y. Shi, J. Org. Chem., 2000, 65, 8807-8810.

Methyltrioxorhenium (MTO) catalyzes an epoxidation of alkenes with 30% aqueous hydrogen peroxide. The addition of 1-10 mol % of 3-cyanopyridine increases the system's efficiency resulting in high isolated yields of the corresponding epoxides. Alkenes yielding epoxides more sensitive to nucleophilic ring opening require a mixture of 3-cyanopyridine and pyridine.
H. Adolfsson, C. Copéret, J. P. Chiang, A. K. Yudin, J. Org. Chem., 2000, 65, 8651-8658.

Bubbling SO₂F₂ gas into a solution of olefin, 30% aqueous hydrogen peroxide, and 2 M aqueous potassium carbonate in 1,4-dioxane at room temperature for 1 h provides the corresponding epoxides in good to excellent yields. This inexpensive, mild, and highly efficient epoxidizing system is suitable to a variety of olefinic substrates including electron-rich and electron-deficient ones.
C. Ai, F. Zhu, Y. Wang, Z. Yan, S. Lin, J. Org. Chem., 2019, 84, 11928-11934.

A non-heme iron complex catalyzes highly enantioselective epoxidation of olefins with H₂O₂ in the presence of catalytic amounts of carboxylic acid additives. Ligand and carboxylic acid synergistically cooperate in promoting efficient O-O cleavage and creating highly chemo- and enantioselective epoxidizing species which provide a broad range of epoxides in synthetically valuable yields and short reaction times.
O. Cussó, I. Garcia-Bosch, X. Ribas, J. Lloret-Fillol, M. Costas, J. Am. Chem. Soc., 2013, 135, 14871-14878.

An efficient epoxidation of a broad range of olefins using hydrogen peroxide as the oxidant has been accomplished in the presence of acetic acid and a manganese catalyst that exhibits an uncommon chemoselectivity.
I. Garcia-Bosch, X. Ribas, M. Costas, Adv. Synth. Catal., 2008, 351, 348-352.

A tungsten-bishydroxamic acid complex promotes a simple, efficient, and environmentally friendly asymmetric epoxidation of allylic, and homoallylic alcohols at room temperature using aqueous hydrogen peroxide as oxidant.
C. Wang, H. Yamamoto, J. Am. Chem. Soc., 2014, 136, 1222-1225.

Homoallylic alcohols were efficiently epoxidized to the corresponding 3,4-epoxy alcohols in excellent yields in the presence of methyltrioxorhenium (MTO) as catalyst, aqueous hydrogen peroxide as the terminal oxidant, and 3-methylpyrazole as an additive. Organic solvent-free conditions accelerate the reaction.
S. Yamazaki, J. Org. Chem., 2012, 77, 9884-9888.

A chiral bisaryl-silyl-protected pyrrolidine acts as a very selective epoxidation organocatalyst using simple oxidation agents. The scope of the reaction is demonstrated by the formation of optically active α,β-epoxy aldehydes in high yields and enantioselectivities. The asymmetric epoxidation reactions proceed also under environmental friendly reaction conditions in, for example, water mixtures of alcohols.
M. Marigo, J. Franzen, T. B. Poulsen, W. Zhuang, K. A. Jorgensen, J. Am. Chem. Soc., 2005, 127, 6284-6289.

A series of 20 chiral epoxides were obtained with excellent yields and enantioselectivities within short reaction times using hybrid amide-based Cinchona alkaloids as catalysts at very low loading. Moreover, the catalyst solution can be reused 10times, without further catalyst addition to the reaction mixture.
M. Majdecki, A. Tyszka-Gumkowska, J. Jurczak, Org. Lett., 2020, 22, 8687-8691.

A chiral N,N'-dioxide/Sc^III complex catalyzes an enantioselective epoxidation of α-substituted vinyl ketones in the presence of H₂O₂ as the oxidant to provide key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields and with good enantioselectivities.
Q. He, D. Zhang, F. Zhang, X. Liu, X. Feng, Org. Lett., 2021, 23, 6795-6800.

An efficient decarboxylative N-formylation of amines with glyoxylic acid provides formamides in good yields. The reaction tolerates a wide range of functional groups under metal free and base free conditions. In addition, large-scale experiments and high chemoselectivity have shown great potential application of this strategy.
J. Wu, Y. Zhang, J. Yang, L. Yu, S. Zhang, J. Zhou, Z. Li, X. Xu, H. Xu, J. Org. Chem., 2023, 88, 13590-13597.

The asymmetric Payne oxidation of N-sulfonyl aldimines catalyzed by a P-spiro chiral triaminoiminophosphorane enables a practical synthesis of optically active N-sulfonyl oxaziridines with high efficiency and an excellent level of enantioselectivity. The versatility of this method was demonstrated by the diastereoselective kinetic oxidation of racemic α-chiral N-sulfonyl imines.
R. Tsutsumi, S. Kim, D. Uraguchi, T. Ooi, Synthesis, 2014, 46, 871-878.

VO(acac)₂ catalyzes the oxidation of aromatic and aliphatic aldehydes to the corresponding acids efficiently and selectively in the presence of hydrogen peroxide as an oxidant. This method offers functional-group compatibility, easy workup procedure, and a short reaction time. The performance of titania-supported VO(acac)₂ in the oxidation of aldehydes was also investigated.
D. Talukdar, K. Sharma, S. K. Bharadwaj, A. J. Thakur, Synlett, 2013, 24, 963-966.

Aromatic aldehydes and benzylic alcohols are rapidly converted into esters derived from methanol, ethanol, iso-propanol, n-butanol, sec-butyl alcohol, and propargylic alcohol without additives in a one-pot manner using a bench-stable V-catalyst and H₂O₂ as a green oxidant. The developed method is compatible with a broad range of functional groups.
G. Mali, I. Verma, H. Arora, A. Rajput, A. Kumar, R. D. Erande, J. Org. Chem., 2023, 88, 5696-5703.

A copper-catalyzed O-methylation of carboxylic acids using dimethyl sulfoxide (DMSO) as the methyl source exhibits a broad substrate scope and excellent functional group tolerance. Mechanistic studies indicate that a methyl radical is generated from dimethyl sulfoxide.
J. Jia, Q. Jiang, A. Zhao, B. Xu, Q. Liu, W.-P. Luo, C.-C. Guo, Synthesis, 2016, 48, 421-428.

A combined amino- and N-heterocyclic carbene (NHC)-catalyzed one-pot reaction sequence using commercially available catalysts at low catalyst loadings gives β-hydroxy and β-amino esters in high yield and excellent enantiopurity. The generation of quaternary stereocenters and application in gram-scale synthesis were also realized, with no requirements of inert or anhydrous reaction conditions.
H. Jiang, B. Gschwend, Ł. Albrecht, K. A. Jørgensen, Org. Lett., 2010, 12, 5052-5055.

A palladium-catalyzed, environmentally friendly dioxygenation reaction of simple alkenes enables a rapid assembly of valuable α-hydroxy ketones with high atom economy.
J. Huang, J. Li, J. Zheng, W. Wu, W. Hu, L. Ouyang, H. Jiang, Org. Lett., 2017, 19, 3354-3357.

An effective epoxidation of lipophilic alkenes using hydrogen peroxide was accomplished with a manganese sulfate/bicarbonate catalytic system in an ionic liquid at room temperature.
K.-H. Tong, K.-Y. Wong, T. H. Chan, Org. Lett., 2003, 5, 3423-3425.

An epoxidation of alkenes using hydrogen peroxide as the terminal oxidant is promoted by catalytic amounts (1.0-0.1 mol %) of manganese(2⁺) salts, and must be performed using at least catalytic amounts of bicarbonate buffer. Various aryl-substituted, cyclic, and trialkyl-substituted alkenes were epoxidized under these conditions using 10 equiv of hydrogen peroxide, but monoalkyl-alkenes were not. Additives such as sodium acetate and salicylic acid enhanced the rate of the desired epoxidation reaction by 2-3 times. Possible mechanisms for the reaction are discussed.
B. S. Lane, M. Vogt, V. J. DeRosa, K. Burgess, J. Am. Chem. Soc., 2002, 124, 11946-11954.

Aryl benzyl selenoxides are efficient catalysts for the epoxidation of various olefinic substrates and the Baeyer-Villiger oxidation of aldehydes and ketones with hydrogen peroxide.
M. A. Goodman, M. R. Detty, Synlett, 2006, 1100-1104.

A highly enantioselective catalytic epoxidation of α,β-unsaturated diaryl enones was achieved with high chemical yield by using aqueous hydrogen peroxide in the presence of a guanidine-urea bifunctional organocatalyst. The catalyst performs cooperatively by interaction of the guanidine group with hydrogen peroxide and the urea group with the enone or vice versa.
S. Tanaka, K. Nagasawa Synlett, 2009, 667-670.

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds take place. Acyclic enones, cyclic enones, and α-branched enals can be converted. Intermediates have been characterized by MS and NMR. DFT calculations explain the activation of H₂O₂.
O. Lifchits, M. Mahlau, C. M. Reisinger, A. Lee, C. Farès, I. Polyak, G. Gopakumar, W. Thiel, B. List, J. Am. Chem. Soc., 2013, 135, 6677-6693.

Chiral primary amine salts catalyze highly enantioselective epoxidations of cyclic enones with hydrogen peroxide.
X. Wang, C. M. Reisinger, B. List, J. Am. Chem. Soc., 2008, 130, 6070-6071.

M. A. Goodman, M. R. Detty, Synlett, 2006, 1100-1104.

Aldehydes undergo oxidative transformation to the methyl esters in methanol as solvent upon treatment with catalytic amounts of vanadium pentoxide in combination with hydrogen peroxide. This method features mild reaction conditions, short reaction times, high efficiencies, cost-effectiveness, and facile isolation of the desired products.
R. Gopinath, B. Patel, Org. Lett., 2000, 2, 577-579.

A convenient and efficient oxidation of hydroxylated and methoxylated benzaldehydes and acetophenones to the corresponding phenols uses hydrogen peroxide and methyltrioxorhenium as catalyst in ionic liquids [bmim]BF₄ and [bmim]PF₆.
R. Bernini, A. Coratti, G. Provenzano, G. Fabrizi, D. Tofani, Tetrahedron, 2005, 61, 1821-1825.

In the presence of catalytic amounts of phosphomolybdic acid (PMA), ethereal hydrogen peroxide reacted readily with a range of epoxides at ambient temperature, giving corresponding β-hydroxyhydroperoxides in good yields.
Y. Li, H.-D. Hao, Y. Wu, Org. Lett., 2009, 11, 2691-2694.

A convenient, safe, and green protocol, that uses oxone/halide and Fenton bromide, achieves a halogenative semipinacol rearrangement at room temperature. The key feature of this method is the green in situ generation of reactive halogenating species from oxidation of halide with oxone or H₂O₂, which produces a nontoxic byproduct (potassium sulfate or water).
L. Song, Y. Zhou, H. Liang, H. Li, Y. Lai, H. Yao, R. Lin, R. Tong, J. Org. Chem., 2023, 88, 504-512.

The acid-catalyzed reaction of β,δ-triketones with hydrogen peroxide produces tricyclic peroxides selectively in good yields via the monoperoxidation of the carbonyl groups in β-position and the transformation of the δ-carbonyl group into an acetal. The resulting peroxides can be easily isolated from the reaction mixture.
A. O. Terent'ev, I. A. Yaremenko, V. V. Chernyshev, V. M. Dembitsky, G. I. Nikishin, J. Org. Chem., 2012, 77, 1833-1842.

The combination of Fe³⁺/H₂O₂ mediates a regioselective alkylation or arylation of alkenes with sulfoxides as alkyl or aryl reagents. Higher alkenes including di-, tri-, and tetra-substituted products were regioselectively synthesized. Both aliphatic and aromatic alkenes could participate in this reaction.
M.-D. Su, Y.-F. Liu, Z.-W. Nie, T.-L. Yang, Z.-Z. Cao, H. Li, W.-P. Luo, Q. Liu, C.-C. Guo, J. Org. Chem., 2022, 87, 7022-7032.

The use of titanium silicalite (TS-1) in a packed-bed microreactor and H₂O₂ in methanol as solvent enable the formation of various pyridine N-oxides in very good yields. This flow process is a safer, greener, and more highly efficiency process than using a batch reactor. The device was used for over 800 hours of continuous operation while while the catalyst remained active.
S. Chen, S. Yang, H. Wang, Y. Niu, Z. Zhang, B. Qian, Synthesis, 2022, 54, 3999-4004.

Nitroso arenes are prepared in good yield from anilines by oxidation with H₂O₂ catalysed with MoO₃/KOH, ammonium molybdate or other molybdenum salts. Further oxidation to nitro arenes is also described.
A. Defoin, Synthesis, 2004, 706-710.

A catalyst-free oxidation of benzylic secondary amines using H₂O₂ in MeOH or CH₂CN provides a selective access to a variety of C-aryl nitrones in good yields.
A. S. Granato, G. W. Amarante, J. Adrio, J. Org. Chem., 2021, 86, 13817-13823.

Oxidation of sulfides with 30% hydrogen peroxide catalyzed by tantalum carbide provides the corresponding sulfoxides in high yields, whereas niobium carbide as catalyst efficiently affords the corresponding sulfones. Both catalysts can easily be recovered and reused without losing their activity.
M. Kirihara, A. Itou, T. Noguchi, J. Yamamoto, Synlett, 2010, 1557-1561.

M. Kirihara, A. Itou, T. Noguchi, J. Yamamoto, Synlett, 2010, 1557-1561.

A versatile procedure oxidizes sulfanes to sulfoxides without any overoxidation to sulfones using a combination of hydrogen peroxide and triflic acid. This method tolerates oxidatively sensitive functional groups.
M. M. Khodaei, K. Bahrami, A. Karimi, Synthesis, 2008, 1682-1684.

2,2,2-Trifluoroacetophenone as organocatalyst enables a cheap, highly efficient, and selective synthesis of sulfoxides and sulfones starting from sulfides in the presence of H₂O₂ as the oxidant. The selectivity depends on the reaction conditions.
E. Voutyritsa, I. Triandafillidi, C. G. Kokotos, Synthesis, 2017, 49, 917-924.

Confined chiral Brønsted acids catalyze asymmetric oxidations of a broad range of sulfides to sulfoxides with hydrogen peroxide. The wide generality and high enantioselectivity of the developed method is comparable even to the best metal-based systems.
S. Liao, I. Čorić, Q. Wang, B. List, J. Am. Chem. Soc., 2012, 134, 10765-10768.

A porphyrin-inspired manganese-catalyzed asymmetric sulfoxidation method enables a rapide oxidation of a broad range of sulfides in high yields with excellent enantioselectivities in the presence of hydrogen peroxide.
W. Dai, J. Li, B. Chen, G. Li, Y. Lv, L. Wang, S. Gao, Org. Lett., 2013, 15, 5658-5661.

Various aromatic and aliphatic sulfides are selectively oxidized to sulfoxides and sulfones in good to excellent yields using 30% H₂O₂ in the presence of a recyclable silica-based tungstate interphase catalyst at room temperature.
B. Karimi, M. Ghoreishi-Nezhad, J. H. Clark, Org. Lett., 2005, 7, 625-628.

Sc(OTf)₃ is an efficient catalyst for the hydrogen peroxide mediated monooxidation of alkyl-aryl sulfides and methyl cysteine containing peptides. The method is high yielding, compatible with many widely used protecting groups, suitable for solid-phase applications and proceeds with minimum over-oxidation.
M. Matteucci, G. Bhalay, M. Bradley, Org. Lett., 2003, 5, 235-237.

An air and moisture tolerant complex of Ti(IV) with a C₃-symmetric triphenolate amine ligand efficiently catalyzes sulfoxidation reactions at room temperature without previous activation using aqueous hydrogen peroxide as oxidant.
M. Mba, L. J. Prins, G. Licini, Org. Lett., 2007, 9, 21-24.

The combination of very high ee values with high yield, the consequence of an efficient initial asymmetric oxidation followed by an efficient kinetic resolution, makes the reported system very practical for the asymmetric oxidation of simple akyl aryl sulfides.
C. Drago, L. Caggiano, R. F. W. Jackson, Angew. Chem. Int. Ed., 2005, 44, 7221-7223.

A chiral Fe(salan) complex serves as an efficient catalyst for asymmetric oxidation of sulfides using hydrogen peroxide in water without surfactant. Not only alkyl aryl sulfides but also various methyl alkyl sulfides were oxidized to the corresponding sulfoxides with high enantioselectivities.
H. Egami, T. Katsuki, J. Am. Chem. Soc., 2007, 129, 8940-8941.

The asymmetric oxidation of sulfides to chiral sulfoxides with hydrogen peroxide in good yield and high enantioselectivity has been catalyzed very effectively by a chiral vanadium-salan complex. The efficient kinetic resolution of racemic sulfoxides catalyzed by the vanadium-salan system is also described.
J. Sun, C. Zhu, Z. Dai, M. Xang, Y. Pan, H. Hu, J. Org. Chem., 2004, 69, 8500-8503.

LiNbMoO₆ catalyzes a chemoselective sulfur oxidation of allylic sulfides containing double bonds of high electron density without any epoxidation. Selective oxidation to either the corresponding sulfoxides or the sulfones was realized by controlling the stoichiometry of the quantitative oxidant, H₂O₂. Various functional groups including hydroxy, formyl, and ethers of THP or TBDMS are tolerated.
S. Choi, J.-D. Yang, M. Ji, H. Choi, M. Kee, K.-H. Whn, S.-H. Byeon, W. Baik, S. Koo, J. Org. Chem., 2001, 66, 8154-8159.

The combination of H₂O₂ and SOCl₂ is a highly reactive reagent for the direct oxidative conversion of thiol derivatives to the corresponding sulfonyl chlorides through oxidative chlorination. Upon reaction with amines, the corresponding sulfonamides were obtained in excellent yields in very short reaction times.
K. Bahrami, M. M. Khodaei, M. Soheilizad, J. Org. Chem., 2009, 74, 9287-9291.

Hydrogen peroxide, in the presence of zirconium tetrachloride, is a very efficient reagent for the direct oxidative conversion of thiols and disulfides into the corresponding sulfonyl chlorides with high purity through oxidative chlorination. Excellent yields, very short reaction times, mild reaction conditions, and the avoidance of harsh reagents are the main advantages of this method.
K. Bahrami, M. M. Khodaei, M. Soheilizad, Synlett, 2009, 2773-2776.

Thiols were effectively oxidized into disulfides by reacting with hydrogen peroxide in the presence of a catalytic amount of iodide ion or iodine.
M. Kirihara, Y. Asai, S. Ogawa, T. Noguchi, A. Hatano, Y. Hirai, Synthesis, 2007, 3286-3289.

Simple, mild, and environmentally friendly procedures for the direct conversion of dithioesters into either carboxylic acids or esters using hydrogen peroxide under alkaline conditions are described.
F. Grellepois, C. Portella, Synthesis, 2008, 3443-3446.

The hydrogen peroxide-zirconium(IV) chloride reagent system is efficient and general for the conversion of thioamides to amides in short reaction times and good chemoselectivity, and allows a simple workup that precludes the use of toxic solvents.
K. Bahrami, M. M. Khodaei, Y. Tirandaz, Synthesis, 2009, 369-371.

A reaction of xanthates, DMSO, and Fenton’s reagent proceeds under very mild conditions to provide various β-keto sulfones in high yields.
P. N. Chalikidi, M. G. Uchuskin, I. V. Trushkov, V. T. Abaev, O. V. Serdyuk, Synlett, 2018, 29, 571-575.

(E)-β-Iodo vinylsulfones are synthesized in very good yields under ultrasound irradiation using alkynes, sulfonyl hydrazides, potassium iodide and hydrogen peroxide. The key features of this protocol are the speed and efficiency of the reactions.
C. Zhou, X. Zeng, Synthesis, 2021, 53, 4614-4620.

The synthesis of a planar-chiral bisflavin catalyst (1) and its use in asymmetric Bayer-Villiger-Oxidations is described.
S. Murahashi, S. Ono, Y. Imada, Angew. Chem. Int. Ed., 2002, 41, 2366-2368.

α-Acetoxylation of ketones catalyzed by iodobenzene using^acetic anhydride and 30% aqueous hydrogen peroxide as the oxidant is an effective and economical method for the preparation of α-acetoxy ketones in good yields.
J. Sheng, Y. Li, M. Tang, B. Gao, G. Huang, Synthesis, 2007, 1165-1168.

Ketones, ketals, and epoxides can be converted to the corresponding hydroperoxides in high yields and with high chemoselectivity by reaction with ethereal H₂O₂ in the presence of a catalytic amount of MoO₂(acac)₂.
X. An, Q. Zha, Y. Wu, Org. Lett., 2019, 21, 1542-1546.

Ketones or ketals were readily converted into the corresponding gem-dihydroperoxides in high yields by treatment with ethereal H₂O₂ at ambient temperature in the presence of phosphomolybdic acid (PMA) as catalyst.
Y. Li, H.-D. Hao, Q. Zhang, Y. Wu, Org. Lett., 2009, 11, 1615-1618.

Visible-light-induced reactions between readily available organoboronic esters and fluoroalkyl acylsilanes enable a divergent synthesis of fluoroalkyl ketones. Under basic conditions, the organoboronate complex intermediates undergo deboronative fluoride elimination, while in combination with peroxide, a 1,2-shift of fluoroalkyl group is favored.
G. Zhou, Z. Guo, S. Liu, X. Shen, J. Am. Chem. Soc., 2024, 146, 4026-4035.

1-Arylethanones and related compounds are rapidly brominated in dioxane with the H₂O₂-HBr aq system, resulting in the replacement of two hydrogen atoms in the methyl group with bromine. The reaction is also accompanied by bromination of the aromatic ring provided that the latter contains electron-donating substituents.
A. O. Terent'ev, S. V. Khodykin, I. B. Krylov, Y. N. Ogibin, G. I. Nikishin, Synthesis, 2006, 1087-1092.

Active methylene compounds can be chemoselectively brominated in high yields using potassium bromide, hydrochloric acid, and hydrogen peroxide at room temperature.
M. Kirihara, S. Ogawa, T. Noguchi, K. Okubo, Y. Monma, I. Shimizu, R. Shimosaki, A. Hatano, Y. Hirai, Synlett, 2006, 2287-2289.

Pd-catalyzed enantioselective diborations of prochiral allenes followed by allylation reactions with primary imines provide vinyl boronates which may be oxidized to give nonracemic Mannich products. Alternatively, enantiomerically enriched homoallylic amine derivatives may be obtained by protonation and Suzuki cross-coupling of the vinyl boronate.
J. D. Sieber, J. P. Morken, J. Am. Chem. Soc., 2006, 128, 74-75.

A simple, mild and efficient procedure cleaves a wide range of ketoximes and aldoximes to the corresponding carbonyl compounds in an aqueous medium using catalytic amounts of potassium bromide and ammonium heptamolybdate tetrahydrate in combination with hydrogen peroxide.
N. C. Ganguly, S. K. Barik, Synthesis, 2008, 425-428.

A selective and efficient oxidative iodination of electron rich arenes was carried out with one equivalent of KI and two equivalents of 30% hydrogen peroxide in MeOH in the presence of strong acid.
J. Iskra, S. Stavber, M. Zupan, Synthesis, 2004, 1869-1873.

A NaBr-catalyzed coupling reaction of Bunte salts with phosphonates enables a simple, green, and efficient synthesis of of thiophosphates in good yields in the presence of an acid and hydrogen peroxide (30%).
C. Min, R. Zhang, Q. Liu, S. Lin, Z. Yan, Synthesis, 2018, 50, 2027-2030.

A ligand-enabled selective γ-C(sp³)-H hydroxylation of a series of primary amines, piperidines, and morpholines using sustainable aqueous hydrogen peroxide provides hydroxylated products with excellent monoselectivity. This method enables the synthesis of a wide range of γ-amino alcohols, β-amino acids, and azetidines.
Z. Li, J.-Q. Yu, J. Am. Chem. Soc., 2023, 145, 25948-25953.

An efficient and highly enantioselective Payne-type oxidation of N-sulfonyl imines exhibits broad substrate generality and unique chemoselectivity based on the combined use of hydrogen peroxide and trichloroacetonitrile under the catalysis of P-spiro chiral triaminoiminophosphorane.
D. Uraguchi, R. Tsutsumi, T. Ooi, J. Am. Chem. Soc., 2013, 135, 8161-8164.

A mild, environmentally friendly, and efficient process enables the synthesis of 2-imidazolines in high yield by reaction of aldehydes with ethylenediamine using hydrogen peroxide as an oxidant in the presence of sodium iodide and anhydrous magnesium sulfate.
G.-y. Bai, K. Xu, G.-f. Chen, Y.-h. Yang, T.-y. Li, Synthesis, 2011, 1599-1603.

A 2,2,2-trifluoroacetophenone-catalyzed oxidation of allyloximes enables a green and efficient synthesis of isoxazolines utilizing H₂O₂ as the oxidant. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated, leading to isoxazolines in good yields.
I. Triandafillidi, C. G. Kokotos, Org. Lett., 2017, 19, 106-109.

An oxidative cleavage of alkyl C-Pd bond by H₂O₂ enables a palladium-catalyzed intramolecular aminohydroxylation to give various heterocycles with good yields and excellent diastereoselectivities. Facile transformation of these products provided a powerful tool toward the synthesis of 2-amino-1,3-diols and 3-ol amino acids. Preliminary mechanistic studies revealed that a S_N2 type attack of water at a high-valent Pd center is involved.
H. Zhu, P. Chen, G. Liu, J. Am. Chem. Soc., 2014, 136, 1766-1769.

Lipase B from Candida antarctica catalyzes the oxidative ring expansion of furfuryl alcohols in the presence of aqueous hydrogen peroxide to yield functionalized pyranones under mild conditions. The corresponding piperidinone derivatives can be obtained by a similar enzymatic rearrangement of N-protected furfurylamines.
F. Blume, P. Sprengart, J. Deska, Synlett, 2018, 29, 1293-1296.

A N-N bond-forming oxidative cyclization enables the synthesis of all three tautomeric forms of indazoles from readily available 2-aminomethyl-phenylamines. The method selectively gives access to various 2-substituted 2H-indazoles which are frequently used in drug design, and to less studied 3H-indazoles
A. S. Toledano, J. Bitai, D. Covini, J. Karolyi-Oezguer, C. Dank, H. Berger, A. Gollner, Org. Lett., 2024, 26, 1229-1232.

A N-N bond-forming oxidative cyclization enables the synthesis of all three tautomeric forms of indazoles from readily available 2-aminomethyl-phenylamines. The method selectively gives access to various 2-substituted 2H-indazoles which are frequently used in drug design, and to less studied 3H-indazoles.
A. S. Toledano, J. Bitai, D. Covini, J. Karolyi-Oezguer, C. Dank, H. Berger, A. Gollner, Org. Lett., 2024, 26, 1229-1232.

A convenient method for the synthesis of 2-substituted benzimidazoles and benzothizoles offers short reaction times, large-scale synthesis, easy and quick isolation of the products, excellent chemoselectivity, and excellent yields as main advantages.
K. Bahrami, M. M. Khodaei, F. Naali, J. Org. Chem., 2008, 73, 6835-6837.

A simple and efficient procedure for the synthesis of substituted benzimidazoles through a one-pot condensation of o-phenylenediamines with aryl aldehydes in the presence of H₂O₂ and HCl in acetonitrile at room temperature features short reaction time, easy and quick isolation of the products, and excellent yields.
K. Bahrami, M. M. Khodaei, I. Kavianinia, Synthesis, 2007, 417-427.

An efficient and environmentally friendly conversion of α-hydroxy N-arylamides into isatins in very good yields proceeded smoothly under metal-free conditions in the presence of hydrogen peroxide as oxidant. This convenient method offers broad substrate scope.
J. Li, X. Cheng, X. Ma, G. Lv, Z. Zhan, M. Guan, Y. Wu, Synlett, 2016, 27, 2485-2488.

The synthesis of chiral 3-monosubstituted oxindoles is a significant challenge due to the ease of racemization. A mild titanium-catalyzed chemo- and enantioselective indole oxidation provides a diverse set of chiral 3-monosubstituted oxindoles with excellent yields and ees in the presence of H₂O₂ as green terminal oxidant. The reaction tolerates a broad range of functional groups.
S. Li, X. Liu, C.-H. Tung, L. Liu, J. Am. Chem. Soc., 2023, 145, 27120-27130.

Peroxy trichloroacetimidic acid, in situ generated from aqueous hydrogen peroxide and trichloroacetonitrile, acts as a competent electrophilic oxygenating agent for a direct enantioselective α-hydroxylation of oxindoles in the presence of a chiral 1,2,3-triazolium salt as a phase-transfer catalyst.
K. Ohmatsu, Y. Ando, T. Ooi, Synlett, 2017, 28, 1291-1294.

A simple protocol for the deprotection of 1,3-dithianes and 1,3-dithiolanes showed tolerance for a number of phenol and amino protecting groups using 30% aqueous hydrogen peroxide activated by iodine catalyst (5 mol%) in water in the presence of sodium dodecyl sulfate (SDS) under essentially neutral conditions without any detectable overoxidation.
N. G. Ganguly, S. K. Barik, Synthesis, 2009, 1393-1399.

Phosphorylation of amines, alcohols, and sulfoximines provides various phosphoramidates, phosphorus triesters and sulfoximine-derived phosphoramidates using molecular iodine as a catalyst and H₂O₂ as the sole oxidant under mild reaction conditions.
J. Dhineshkumar, K. R. Prabhu, Org. Lett., 2013, 15, 6062-6065.

Vanadium pentoxide very effectively promotes the bromination of organic substrates, including selective bromination of some aromatics, by tetrabutylammonium bromide in the presence of hydrogen peroxide. The reaction offers mild conditions, high selectivity, yield, and reaction rate, and redundancy of bromine and hydrobromic acid.
U. Bora, G. Bose, M. K. Chaudhuri, S. S. Dhar, R. Gopinath, A. T. Khan, B. K. Patel, Org. Lett., 2000, 2, 247-249.