Categories: O-H Bond Formation >
Reduction of carboxyl compounds to alcohols
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Recent Literature
A catalytic system of cobalt(II) chloride and diisopropylamine in combination
with NaBH4 showed excellent activity in the chemoselective reduction
of various carboxylic esters to their corresponding alcohols in very good
yields under mild conditions. Unsaturated carboxylic esters give saturated
alcohols in high yields.
A. R. Jagdale, A. S. Paraskar, A. Sudalai, Synthesis, 2009,
660-664.
Odorless Dod-S-Me and MMS are developed as efficient borane carriers. The
yields of hydroborations and reductions with the borane complex of Dod-S-Me
are very high. The recovery of Dod-S-Me after the reaction is quantitative.
P. K. Patra, K. Nishide, K. Fuji, M. Node, Synthesis, 2004,
1003-1006.
A simple and practical protocol for the reduction of carboxylic acids via in
situ formation of hydroxybenzotriazole esters followed by reaction with sodium
borohydride gives the corresponding alcohols. The reaction proceeds with
excellent yields in the presence of water.
J. A. Morales-Serna, E. García-Rios, J. Bernal, E. Paleo, R. Gaviño, J. Cárdenas, Synthesis, 2011,
1375-1382.
The preparation of alkenyl halides of any length from inexpensive starting
reagents is reported. Standard organic transformations were used to prepare
straight-chain α-olefin halides in excellent overall yields with no
detectable olefin isomerization and full recovery of any unreacted starting
material.
T. W. Baughman, J. C. Sworen, K. B. Wagener, Tetrahedron, 2004, 60, 10943-10948.
The use of diethylaluminum benzenethiolate enables an efficient discrimination
between aldehydes and other carbonyl functions and allows a chemoselective in
situ reduction of ketones and methyl esters in the presence of aldehydes without
using traditional protecting group methodologies.
G. Bastug, S. Dierick, F. Lebreux, I. E. Markó, Org. Lett., 2012,
14, 1306-1309.
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