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)
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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