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Chemicals >> Reducing Agents

Isopropanol, 2-Propanol

see also: 2-butanol

Name Reactions

Meerwein-Ponndorf-Verley Reduction (MPV)

Recent Literature

[Cp*Ir(2,2′-bpyO)(H2O)] is a highly efficient and general catalyst for transfer hydrogenation of carbonyl compounds and chemoselective transfer hydrogenation of unsaturated aldehydes with isopropanol under neutral conditions. The reaction tolerates deducible groups such as nitro, cyano, ester, and halide.
R. Wang, Y. Tang, M. Xu, C. Meng, F. Li, J. Org. Chem., 2018, 83, 2274-2281.

Catalytic MPV reduction was successfully carried out using iPrOH as the reducing agent and simple alkylaluminum reagents as precatalysts, that were converted to highly active low-aggregation aluminum alkoxides. When chiral hydride sources were utilized in the reduction of 2-chloroacetophenone, high enantioselectivity was observed.
E. J. Campbell, H. Zhou, S. T. Nguyen, Org. Lett., 2001, 3, 2391-2393.

A very simple and inexpensive catalytic system based on abundant manganese as transition metal and on an inexpensive phosphine-free bidendate ligand enables the reduction of a broad range of carbonyl derivatives with 2-propanol as hydrogen donor at room temperature. The reaction runs with low catalyst loading and exhibits a good functional group tolerance.
A. Bruneau-Voisine, D. Wang, V. Dorcet, T. Roisnel, C. Darcel, J.-B. Sortais, Org. Lett., 2017, 19, 3656-3659.

Indium tri(isopropoxide)-catalyzed Meerwein-Ponndorf-Verley reduction of aliphatic and aromatic aldehydes in 2-propanol gave selectively the corresponding primary alcohols in good to excellent yields at room temperature. The reaction tolerates a wide range of functional groups including alkene, ether, ketone, ester, nitrile, and nitro.
J. Lee, T. Ryu, S. Park, P. H. Lee, J. Org. Chem., 2012, 77, 4821-4825.

A convenient disproportionation or reduction of aldehydes is promoted by lithium bromide and triethylamine in a solvent-free environment at room temperature. Products of Cannizzaro or Tishchenko reactions can be isolated using different workup methods. In the presence of a hydrogen donor alcohol, a Meerwein-Ponndorf-Verley reaction takes place.
M. M. Mojtahedi, E. Akbarzadeh, R. Sharifi, M. S. Abaee, Org. Lett., 2007, 9, 2791-2793.

The reduction of ketones and aldehydes with lanthanide metals (La, Ce, Sm, Yb) and a catalytic amount of iodine (5 mol %) in iPrOH proceeded smoothly to produce the corresponding alcohols as the major products in good yield, while in THF, methanol, and ethanol the pinacols were mainly produced. The yields of alcohols were improved most effectively by the use of Sm metal.
S.-I. Fukuzawa, N. Nakano, T. Saitoh, Eur. J. Org. Chem., 2004, 2863-2867.

A Mild and Efficient Flow Procedure for the Transfer Hydrogenation of Ketones and Aldehydes using Hydrous Zirconia
C. Battilocchio, J. M. Hawkins, S. V. Ley, Org. Lett., 2013, 15, 2278-2281.

Pincer-aryl ruthenium(II) complexes form active catalysts in the reduction of ketones by hydrogen transfer in iPrOH using KOH as promoter. At a KOH/Ru molar ratio of 20/1 only trace amounts of aldol products are formed. Under these conditions, the σ Ru-C bond is stable and the [Ru(PCP)PPh3] fragment is preserved.
P. Dani, T. Karlen, R. A. Gossage, S. Gladiali, G. van Koten, Angew. Chem., 2000, 112, 759-761.

An asymmetric α-alkylative reduction of prochiral ketones with primary alcohols has been disclosed. The reaction is catalyzed by both iridium and ruthenium complexes and gave optically active alcohols with elongation of the carbon skeleton with high enantioselectivity.
G. Onodera, Y. Nishibayashi, S. Uemura, Angew. Chem. Int. Ed., 2006, 45, 3819-3822.

In the presence of a phenol ligand, a cationic ruthenium hydride complex exhibited high catalytic activity for the hydrogenolysis of carbonyl compounds to yield the corresponding aliphatic products. The reaction showed exceptionally high chemoselectivity toward the carbonyl reduction over alkene hydrogenation.
N. Kalutharage, C. S. Yi, J. Am. Chem. Soc., 2015, 137, 11105-11114.

Nickel nanoparticles catalyse the reductive amination of aldehydes by transfer hydrogenation with isopropanol at 76°C.
F. Alonso, P. Riente, M. Yus, Synlett, 2008, 1289-1292.

A nickel-catalyzed enantioselective transfer hydrogenation of N-sulfonyl imines offers excellent α-selectivity. The use of inexpensive 2-propanol-d8 as a deuterium source enables a deuteration with high deuterium content. In addition, no deuteration of β-C-H and the remote C-H of N-sulfonyl amines occurred, which is hard to achieve using other imines or by hydrogen isotope exchange with D2O.
P. Yang, L. Zhang, K. Fu, Y. Sun, X. Wang, J. Yue, Y. Ma, B. Tang, Org. Lett., 2020, 22, 8278-8284.

A selective transfer hydrogenation of α,β-unsaturated carbonyl compounds to saturated ones in very good yields was achieved by the use of 2-propanol as a hydrogen donor under the influence of catalytic amounts of [Ir(cod)Cl]2, 1,3-bis(diphenylphosphino)propane (dppp), and Cs2CO3. The reduction of carbonyl compounds to alcohols can also promoted by the same catalytic system.
S. Sakaguchi, T. Yamaga, Y. Ishii, J. Org. Chem., 2001, 66, 4710-4712.

Enantioselective transfer hydrogenation of 1,1-dimethylallene in the presence of aldehydes and 2-propanol or primary alcohols without 2-propanol employing a cyclometalated iridium C,O-benzoate derived from allyl acetate, m-nitrobenzoic acid, and (S)-SEGPHOS delivers reverse-prenylation products in very good yields and enantioselectivities.
S. B. Han, I. S. Kim, H. Han, M. J. Krische, J. Am. Chem. Soc., 2009, 131, 6916-6917.

Two complementary dual catalytic systems enable a highly regioselective reductive hydration of terminal alkynes to yield branched or linear alcohols in very good yield. The method is compatible with terminal, di-, and trisubstituted alkenes. This reductive hydration constitutes a strategic surrogate to alkene oxyfunctionalization and may be of utility in multistep settings.
L. Li, S. B. Herzon, J. Am. Chem. Soc., 2012, 134, 17376-17378.

L. Li, S. B. Herzon, J. Am. Chem. Soc., 2012, 134, 17376-17378.

In a highly regio- and stereoselective hydroarylation, hydroalkenylation, and hydrobenzylation of ynol ethers, a Pd-catalyzed reductive addition of organohalides, including aryl, alkenyl, and benzyl halides, in the presence of 2-propanol gives α,β- and β,β-disubstituted olefinic ethers in good yields.
W. Cui, J. Yin, R. Zheng, C. Cheng, Y. Bai, G. Zhu, J. Org. Chem., 2014, 79, 3487-3493.

Rh(III) catalyzes an intermolecular anti-Markovnikov hydroamidation of unactivated alkenes with dioxazolone amidating reagents and isopropanol as hydride source under mild conditions. The reaction tolerates a wide range of functional groups and efficiently converts also electron-deficient, styrenes, and 1,1-disubstituted alkenes to their corresponding linear amides.
N. Wagner-Carlberg, T. Rovis, J. Am. Chem. Soc., 2022, 144, 22426-22432.

A dimeric Ni(I) catalyst and an exogenous alkoxide base promote Markovnikov-selective hydroarylation (alkenylation) of unactivated and activated olefins using organo bromides or triflates derived from widely available phenols and ketones. Products bearing aryl- and alkenyl-substituted tertiary and quaternary centers could be isolated in very good yield and excellent regioisomeric ratios.
C.-F. Liu, X. Luo, H. Wang, M. J. Koh, J. Am. Chem. Soc., 2021, 143, 9498-9506.

Aryl halides are reduced into the corresponding arenes in high yields, using 2-propanol as reductant and solvent, cesium carbonate as base, and di-tert-butyl peroxide (or di-tert-butyl hyponitrite) as radical initiator. This simple system reduces various aryl bromides and iodides through a SET mechanism with high functional-group tolerance.
R. Ueno, T. Shimizu, E. Shirakawa, Synlett, 2016, 27, 747-744.

A simple and efficient Ru(II)-catalyzed transfer hydro-dehalogenation using 2-propanol as the hydride source is applicable for various aromatic halides and α-haloesters and amides. The potential synthetic application of this method was demonstrated by efficient gram-scale transformation with catalyst loading as low as 0.5 mol %.
T. You, Z. Wang, J. Chen, Y. Xia, J. Org. Chem., 2017, 82, 1340-1346.

A nickel-catalyzed hydrodeoxygenation of aryl sulfamates enables the use of alcohols as mild reductants. A variety of functional groups and heterocycles were tolerated in this reaction system to give the desired products in high yields.
K. Matsuo, M. Kuriyama, K. Yamamoto, Y. Demizu, K. Nishida, O. Onomura, Synthesis, 2021, 53, 4449-4460.

Transfer hydrogenation of chiral α,β-unsaturated N-(tert-butylsulfinyl)ketimines followed by removal of the sulfinyl group provides primary allylic amines with enantiomeric excesses from 97 to >99%.
E. Selva, Y. Sempere, D. Ruiz-Martínez, O. Pablo, D. Guijarro, J. Org. Chem., 2017, 82, 13693-13699.

A continuous flow method for the selective reduction of aromatic nitriles to the corresponding primary amines is based on a ruthenium-catalysed transfer-hydrogenation process with isopropanol as both solvent and reducing agent.
R. Labes, D. González-Calderón, C. Battilocchio, C. Mateos, G. R. Cumming, O. de Frutos, J. A. Rincón, S. V. Ley, Synlett, 2017, 28, 2855-2858.

Reductive dimerization of nitrosobenzenes enables an effective and simple preparation of substituted azoxybenzenes without additional catalysts/reagents. This procedure can be applied to substrates with a wide range of substitution patterns.
Y.-F. Chen, J. Chen, L.-J. Lin, G. J. Chuang, J. Org. Chem., 2017, 82, 11620-11630.

The use of i-PrOH as environmentally benign hydrogen surrogate enables a ligand-free Co-catalyzed chemoselective reductive cyclization cascade of enone-tethered aldehydes. The selectivity between Michael-Aldol cycloreduction cascade and oxa-Michael cascade can be adjusted by the addition of TEMPO as a steric Lewis bases to provide 1H-indenes and dihydroisobenzofurans, respectively.
S.-S. Ma, B.-L. Jiang, Z.-K. Yu, S.-J. Zhang, B.-H. Xu, Org. Lett., 2021, 23, 3873-3878.

The use of i-PrOH as environmentally benign hydrogen surrogate enables a ligand-free Co-catalyzed chemoselective reductive cyclization cascade of enone-tethered aldehydes. The selectivity between Michael-Aldol cycloreduction cascade and oxa-Michael cascade can be adjusted by the addition of TEMPO as a steric Lewis bases to provide 1H-indenes and dihydroisobenzofurans, respectively.