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Visible-Light-Mediated Nucleophilic Addition of an α-Aminoalkyl Radical to Isocyanate or Isothiocyanate

Hongxia Zhou, Ping Lu, Xiangyong Gu and Pixu Li*

*Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering, and Materials Science, Soochow University, 199 RenAi Road, Suzhou, Jiangsu, 215123, China, Email: lipixusuda.edu.cn

H. Zhou, P. Lu, X. Gu, P. Li, Org. Lett., 2013, 15, 5646-4649.

DOI: 10.1021/ol402573j


Abstract

Bis[2-(4,6-difluorophenyl)pyridinato-C2,N](picolinato)iridium(III) (FIrpic) is an effective catalyst of a visible-light photoredox reaction of N,N-dimethylaniline derivatives and aryl isocyanates or aryl isothiocyanates to yield α-amino amides or α-amino thioamides. The reaction involves generation of α-aminoalkyl radicals from tertiary amines, followed by radical addition to the electron-deficient carbon of the isocyanates or isothiocyanates.

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Key Words

α-amino amides


ID: J54-Y2013