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Deoxygenations

Name Reactions


Barton-McCombie Reaction


Clemmensen Reduction


Wolff-Kishner Reduction


Recent Literature


A direct reduction of alcohols to the corresponding alkanes using chlorodiphenylsilane as hydride source in the presence of a catalytic amount of InCl3 showed high chemoselectivity for benzylic alcohols, secondary alcohols and tertiary alcohols while not reducing primary alcohols and functional groups that are readily reduced by standard methods such as esters, chloro, bromo, and nitro groups.
M. Yasuda, Y. Onishi, M. Ueba, T. Miyai, A. Baba, J. Org. Chem., 2001, 7741-7744.


Aliphatic carboxyl derivatives (acids, acyl chlorides, esters) and aldehydes were efficiently reduced to the methyl group by HSiEt3 in the presence of catalytic amounts of B(C6F5)3.
V. Gevorgyan, M. Rubin, J.-X. Liu, Y. Yamamoto, J. Org. Chem, 2000, 66, 1672-1675.


Salicylic acids and alcohols can be reduced to 2-methylphenols by a simple two steps procedure. Reaction conditions were optimized carrying out a study on the solvent effect and the amount of the reducing agent. The improved procedure resulted particularly useful in the synthesis of deuterated building blocks of biological interest.
F. Mazzini, P. Salvadori, Synthesis, 2005, 2479-2481.


M. Couturier, J. L. Tucker, B. M. Andresen, P. Dube, J. T. Negri, Org. Lett., 2001, 3, 465-467.


An indium(III) hydroxide-catalyzed reaction of carbonyls and chlorodimethylsilane afforded the corresponding deoxygenative chlorination products. Ester, nitro, cyano, or halogen groups were not affected during the reaction course. Typical Lewis acids such as TiCl4, AlCl3, and BF3ˇOEt2 showed no catalytic activity. The reaction mechanism is discussed.
Y. Onishi, D. Ogawa, M. Yasuda, A. Baba, J. Am. Chem. Soc., 2002, 124, 13690-13691.