The primary alcohols 1a-e and ethers 4a-d were effectively reduced to the corresponding hydrocarbons 2 by HSiEt3 in the presence of catalytic amounts of B(C6F5)3. To the best of our knowledge, this is the first example of catalytic use of Lewis acid in the reduction of alcohols and ethers with hydrosilanes. The secondary alkyl ethers 4j,k enabled cleavage and/or reduction under similar reaction conditions to produce either the silyl ethers 3m-n or the corresponding alcohol 5a upon subsequent deprotection with TBAF. It was found that the secondary alcohols 1g-i and tertiary alcohol 1j, as well as the tertiary alkyl ether 4l, did not react with HSiEt3/(B(C6F5)3 reducing reagent at all. The following relative reactivity order of substrates was found: primary >> secondary > tertiary. A plausible mechanism for this nontraditional Lewis acid catalyzed reaction is proposed.
ASJC Scopus subject areas
- Organic Chemistry