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Chemistry. 2015 Oct 12;21(42):14737-41. doi: 10.1002/chem.201502942. Epub 2015 Aug 31.

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

Author information

1
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86)21-54925533.
2
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86)21-54925533. huangzh@sioc.ac.cn.

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.

KEYWORDS:

borates; esters; homogeneous catalysis; silanes; triethylboranes

PMID:
26332613
DOI:
10.1002/chem.201502942

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