Categories: O-H Bond Formation >
Reduction of carboxyl compounds to alcohols
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.