Categories: C-H Bond Formation >
Deoxygenations
Name Reactions
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.
