Copper(II) triflate-catalyzed reduction of carboxylic acids to alcohols and reductive etherification of carbonyl compounds

A protocol is described for the reduction of carboxylic acids to primary alcohols using 1,1,3,3-tetramethyldisiloxane (TMDS) and a catalytic amount of Cu(OTf)2. Aliphatic as well as aromatic carboxylic acids are reduced in high selectivity and good yields. TMDS/Cu(OTf)2 has also been found to be an...

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Bibliographic Details
Published in:Tetrahedron 2012-09, Vol.68 (36), p.7400-7407
Main Authors: Zhang, Yin-Jie, Dayoub, Wissam, Chen, Guo-Rong, Lemaire, Marc
Format: Article
Language:English
Subjects:
1,1,3,3-Tetramethyldisiloxane (TMDS)
Alcohol
Alcohols
Aliphatic compounds
Carbonyl compounds
Carboxylic acid
Carboxylic acids
Catalysis
Catalysts
Chemical Sciences
Chemistry
Copper(II) triflate
Ethers
Exact sciences and technology
Organic chemistry
Preparations and properties
Reduction
Symmetrical ether
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Summary:A protocol is described for the reduction of carboxylic acids to primary alcohols using 1,1,3,3-tetramethyldisiloxane (TMDS) and a catalytic amount of Cu(OTf)2. Aliphatic as well as aromatic carboxylic acids are reduced in high selectivity and good yields. TMDS/Cu(OTf)2 has also been found to be an efficient catalytic reducing system for the preparation of symmetrical ethers from carbonyl compounds under mild conditions. [Display omitted] A protocol is described for the reduction of carboxylic acids to primary alcohols using 1,1,3,3-tetramethyldisiloxane (TMDS) and a catalytic amount of Cu(OTf)2. Aliphatic as well as aromatic carboxylic acids are reduced in high selectivity and good yields. TMDS/Cu(OTf)2 has also been found to be an efficient catalytic reducing system for the preparation of symmetrical ethers from carbonyl compounds under mild conditions.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.06.080