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

Chen Cheng and Maurice Brookhart*

*Department of Chemistry, The University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States, Email: mbrookhartunc.edu

C. Cheng, M. Brookhart, J. Am. Chem. Soc., 2012, 134, 11304-11307.

DOI: 10.1021/ja304547s (free Supporting Information)


Abstract

Reduction of secondary amides to imines and secondary amines has been achieved using low catalyst loadings of readily available iridium catalysts such as [Ir(COE)2Cl]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 shows high efficiency and an appreciable level of functional group tolerance.

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Key Words

reduction of amides, diethylsilane


ID: J48-Y2012-2270