A novel reduction of alcohols and ethers with a HSiEt3catalytic B(C6F5)3 system

Abstract The primary alcohols 1a-d and ethers 4a-b were effectively reduced into the corresponding hydrocarbons 2 by HSiEt 3 in the presence of catalytic amounts of B(C 6 F 5 ) 3 . The secondary alkyl ethers 4g,h underwent cleavage and/or reduction under similar reaction conditions to produce either the silyl ether 3k or the corresponding alcohol 5b upon subsequent deprotection with TBAF. The secondary alcohols ( 1g,h ) and tertiary alcohol 1i , as well as tertiary alkyl ether 4i , did not react with the HSiEt 3 ( B(C 6 F 5 ) 3 reducing reagent at all. The following relative reactivity order of substrates was found: primary⪢secondary>tertiary. The methyl aryl ethers 4c-e and alkyl aryl ether 4f were smoothly deprotected to give the corresponding silyl ethers 3b,h-j in nearly quantitative isolated yields.