Metal-Free Reduction of Secondary and Tertiary N-Phenyl Amides by Tris(pentafluorophenyl)boron-Catalyzed Hydrosilylation

Ryan C. Chadwick, Vladimir Kardelis, Philip Lim and Alex Adronov*

*Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario L8S 4M1, Canada, Email: adronovmcmaster.ca

R. C. Chadwick, V. Kardelis, P. Lim, A. Adronov, J. Org. Chem., 2014, 79, 7728-7733.

DOI: 10.1021/jo501299j

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Abstract

Tris(pentafluorophenyl)boron B(C₆F₅)₃ is an effective catalyst for the reduction of tertiary and N-phenyl secondary amides in the presence of a silane. Various amides can be reduced in near quantitative yield, with minimal purification, at low temperatures, and with short reaction times. This reduction tolerates alkenes, nitro groups, and aryl halides, including aryl iodides.

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Key Words

reduction of amides, tetramethyldisiloxane

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ID: J42-Y2014