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A Metal and Base-Free Chemoselective Primary Amination of Boronic Acids Using Cyanamidyl/Arylcyanamidyl Radical as Aminating Species: Synthesis and Mechanistic Studies by Density Functional Theory

Nachiketa Chatterjee, Minhajul Arfeen, Prasad V. Bharatam and Avijit Goswami*

*Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Rupnagar 140001, Punjab, India, Email: agoswamiiitrpr.ac.in

N. Chatterjee, M. Arfeen, P. V. Bharatam, A. Goswami, J. Org. Chem., 2016, 81, 5120-5127.

DOI: 10.1021/acs.joc.6b00671 (free Supporting Information)


Abstract

An efficient, metal and base-free, chemoselective reaction of boronic acids with cyanamidyl/arylcyanamidyl radicals provides primary aryl-, heteroaryl-, and alkyl amines at ambient temperature within 1 h. The reaction is mediated by PIFA and NBS.

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Key Words

anilines, alkyl amines, benzyl amines, PIFA, NBS


ID: J42-Y2016