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Iridium-catalyzed Reduction of Secondary Amides to Secondary Amines and Imines by Diethylsilane

Chen Cheng, Maurice Brookhart

J Am Chem Soc. 2012 Jul 18;134(28):11304-7.

PMID: 22770123

Abstract:

Catalytic reduction of secondary amides to imines and secondary amines has been achieved using readily available iridium catalysts such as [Ir(COE)(2)Cl](2) with diethylsilane as reductant. The stepwise reduction to secondary amine proceeds through an imine intermediate that can be isolated when only 2 equiv of silane is used. This system requires low catalyst loading and shows high efficiency (up to 1000 turnovers at room temperature with 99% conversion have been attained) and an appreciable level of functional group tolerance.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP542916 Diethylsilane Diethylsilane 542-91-6 Price
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