Synthesis of nitro compounds

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Primary nitroalkanes can be easily obtained in aqueous medium by reaction of alkyl bromides or alkyl iodides with silver nitrite in satisfactory to good yields even in the presence of other functionalities.
R. Ballini, L. Barboni, G. Giarlo, J. Org. Chem., 2004, 69, 6907-6908.

An efficient Pd-catalyzed transformation of aryl chlorides, triflates, and nonaflates to nitroaromatics proceeds under weakly basic conditions and displays a broad scope and excellent functional group compatibility. Moreover, this method allows the synthesis of aromatic nitro compounds that cannot be accessed efficiently via other nitration protocols.
B. P. Fors, S. L. Buchwald, J. Am. Chem. Soc., 2009, 131, 12898-12899.

Triflyl nitrate (TfONO₂) and trifluoroacetyl nitrate (CF₃CO₂NO₂), generated via metathesis in the readily available ethylammonium nitrate (EAN) ionic liquid as solvent, are powerful electrophilic nitrating reagents for a wide variety of aromatic and heteroaromatic compounds. Comparative nitration experiments indicate that EAN/Tf₂O is superior to EAN/TFAA for nitration of strongly deactivated systems.
G. Aridoss, K. K. Laali, J. Org. Chem., 2011, 76, 8088-8094.

Dinitro-5,5-dimethylhydantoin (DNDMH) serves as an arene nitration reagent with good functional group tolerance. Among the two N-nitro units of DNDMH, only the N-nitro unit on N1 was delivered to the nitroarene products.
F. Jia, A. Li, X. Hu, Org. Lett., 2023, 25, 4605-4609.

An ipso nitration of aryl boronic acid derivatives using fuming nitric acid as the nitrating agent provides efficient and chemoselective access to a variety of aromatic nitro compounds. Preliminary reported reactions with different activating agents likely generate anhydrous HNO₃ as common active reagent and the •NO₂ radical as the active species too.
J. I. Murray, M. V. Silva Elipe, K. D. Baucom, D. B. Brown, K. Quasdorf, S. Caille, J. Org. Chem., 2022, 87, 1977-1985.

Photocatalytic and metal-free ipso-nitrations of readily available boronic acid derivatives provide various aromatic and heteroaromatic nitro compounds in very good yields using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility.
K. Zhang, A. Budinská, A. Passera, D. Katayev, Org. Lett., 2020, 22, 2714-2719.

The ionic liquid 1,3-disulfonic acid imidazolium nitrate {[Dsim]NO₃} can be used as nitrating agent for the ipso-nitration of various arylboronic acids and nitro-Hunsdiecker reaction of different α,β-unsaturated acids and benzoic acid derivatives to give various nitroarenes and nitroolefins without using any cocatalysts and solvents under mild conditions.
M. Zarei, E. Noroozizadeh, A. R. Moosavi-Zare, M. A. Zolfigol, J. Org. Chem., 2018, 83, 3645-3650.

PIFA mediates a nitration of aryl amines in the presence of MeNO₂ as solvent and H₂O as cosolvent via NO₂ transfer. Using H₂O as the solvent, the C(sp²)-H functionalization shifts to an α-C(sp³)-H functionalization (cyanation or oxygenation) of the α-C(sp³)-H of cyclic amines.
C. Mudithanapelli, L. P. Dhorma, M.-h. Kim, Org. Lett., 2019, 21, 3098-3102.

The nitration of phenolic compounds with 60% nitric acid has been carried out in the presence of metal-modified montmorillonite KSF and KSF or nitric acid treated HKSF, as catalysts. These catalysts showed good stabilities and high catalytic activities in the nitration process and can be reused. This process is eco-safe and environmentally benign.
W.-P. Yin, M. Shi, Tetrahedron, 2005, 61, 10861-10867.

A mixture of nitrate salt and chlorotrimethylsilane is an efficient, convenient, and regioselective nitrating agent for the ipso-nitration of arylboronic acids to produce the corresponding nitroarenes in moderate to excellent yields.
G. K. S. Prakash, C. Panja, T. Mathew, V. Surampudi, N. A. Petasi, G. A. Olah, Org. Lett., 2004, 6, 2205-2207.

A clay-supported copper nitrate (Claycop) and a catalytic amount of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl enable an inexpensive and mild reagent system for the nitration of a wide variety of aromatic and aliphatic olefins. High conversions and exclusive E-selectivity, together with the environmentally benign nature of the Claycop reagent, make this a green method and an attractive alternative to established methods.
E. Begari, C. Singh, U. Nookaraju, P. Kumar, Synlett, 2014, 25, 1997-2000.

A wide range of olefins with diverse functionalities has been nitrated in synthetically useful yields in a single step under metal-free conditions. This transformation is operationally simple and exhibits excellent E-selectivity. Furthermore, site selective nitration in a complex setup makes this method advantageous.
S. Maity, T. Naveen, U. Sharma, D. Maiti, Org. Lett., 2013, 15, 3384-3387.

Ferric nitrate with catalytic TEMPO is a useful combination of reagents for regio- and stereoselective nitration of various aromatic, aliphatic, and heteroaromatic olefins. This mild and operationally simple reaction provided nitroolefins in preparatively useful yields with excellent E-selectivity.
T. Naveen, S. Maity, U. Sharma, D. Maiti, J. Org. Chem., 2013, 78, 5949-5954.

Triflyl nitrate is an effective nitrating agent for a wide range of unsaturated substrates to form nitro olefins. The reagent is easily generated from tetra-n-butylammonium nitrate in CH₂Cl₂ solution.
G. S. Reddy, E. J. Corey, Org. Lett., 2021, 23, 3379-3383.

A Fe(III)/pyridine-mediated decarboxylative nitration of α,β-unsaturated acids with iron nitrate provides (E)-nitroolefins in good yields. A series of α,β-unsaturated acids are well tolerated in this procedure.
Z. Yang, J. Li, J. Hua, T. Yang, J. Yi, C. Zhou, Synlett, 2017, 28, 1079-1082.

Radical halo-nitration of alkenes proceeds easily by radical addition of nitrogen dioxide generated by thermal decomposition of iron(III) nitrate nonahydrate and subsequent trapping of the resultant radical by a halogen atom in the presence of a halogen salt. Application of this method to synthesis of nitroalkenes is also described.
T. Taniguchi, T. Fuji, H. Ishibashi, J. Org. Chem., 2010, 75, 8126-8132.

The iodonitration of alkynes with I₂ and tBuONO enables a convenient synthesis of β-iodonitro alkenes.
Y. Fan, B. Zhou, K. Chen, B. Wang, X. Li, X. Xu, Synlett, 2017, 28, 1657-1659.

T. Taniguchi, T. Fuji, H. Ishibashi, J. Org. Chem., 2010, 75, 8126-8132.

A domino palladium-catalyzed nitration of Meyer-Schuster intermediates, which were generated in situ from propargylic alcohols, with t-BuONO provides α-nitro enones in very good yields at room temperature with a broad functional group tolerance.
Y. Lin, W. Kong, Q. Song, Org. Lett., 2016, 18, 3702-3705.