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Silatrane as a Practical and Selective Reagent for the Reduction of Aryl Aldehydes to Benzylic Alcohols
Author(s) -
Skrypai Vladislav,
Hurley Joseph J. M.,
Adler Marc J.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501599
Subject(s) - chemistry , reagent , aryl , silane , organic chemistry , reducing agent , combinatorial chemistry , selective reduction , aldehyde , catalysis , alkyl
Hydrosilanes are cheap, readily available substrates, yet they do not see as extensive use for simple carbonyl reductions as borohydrides. Hydrosilane reducing agents broadly fall into one of two general categories: either a) they are easy to handle and require expensive and/or hazardous additives, or b) they are difficult and/or dangerous to handle. This work details the discovery of mild and functional group compatible conditions utilizing hydrosilatrane for the selective reduction of aryl aldehydes to benzylic alcohols without unwanted formation of ethers or deoxygenated products. This method offers significant advances in silane reductions as silatrane is an air‐ and moisture‐stable yet relatively reactive reducing agent that can be used in benchtop open air reactions.