Transition-Metal-Free Transfer Hydrogenative Cascade Reaction of Nitroarenes with Amines/Alcohols: Redox-Economical Access to Benzimidazoles

Arup K. Kabi, Raghuram Gujjarappa, Anupam Roy, Abhishek Sahoo, Dulal Musib, Nagaraju Vodnala, Virender Singh and Chandi C. Malakar*

*Department of Chemistry, National Institute of Technology Manipur, Langol, Imphal - 795004, Manipur, India, Email: chdeepmgmail.com

A. K. Kabi, R. Gujjarappa, A. Roy, A. Sahoo, D. Musib, N. Vodnala, V. Singh, C. C. Malakar, J. Org. Chem., 2021, 86, 14597-14607.

DOI: 10.1021/acs.joc.1c01450

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Abstract

An efficient transition-metal-free transfer hydrogenative cascade reaction between ortho-nitroanilines and benzyl amines or alcohols provides benzimidazoles in good yields using a combination of KOtBu and Et₃SiH as reagents. The reaction conditions tolerate diverse functional groups.

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proposed mechanism

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Key Words

benzimidazoles, triethylsilane

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ID: J42-Y2021