A General, Practical Triethylborane-Catalyzed Reduction of Carbonyl Functions to Alcohols

Chemistry : a European Journal
Dongjie PengZheng Huang

Abstract

A combination of the abundant and low-cost triethylborane and sodium alkoxide generates a highly efficient catalyst for reduction of esters, as well as ketones and aldehydes, to alcohols using an inexpensive hydrosilane under mild conditions. The catalyst system exhibits excellent chemoselectivity and a high level of functional group tolerance. Mechanistic studies revealed a resting state of sodium triethylalkoxylborate that is the product of the reaction of BEt3 with sodium alkoxide. This borate species reacts with hydrosilane to form NaBEt3 H, which rapidly reduces esters.

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Citations

May 17, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Álvaro Raya-BarónIgnacio Fernández
Oct 14, 2017·Science·Stephan C HammerFrances H Arnold
Jun 18, 2021·The Journal of Organic Chemistry·Nhan N H TonThanh Vinh Nguyen
Nov 18, 2018·The Journal of Organic Chemistry·Yiding ChenSteven V Ley
Apr 24, 2019·The Journal of Organic Chemistry·Wubing YaoZheng Huang

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