Radical Fixation of Functionalized Carbon Resources: α-sp3C-H Carbamoylation of Tertiary Amines with Aryl Isocyanates

…, K Matsuda, H Nagaoka, K Tsukamoto, T Tanaka

Index: Yoshimitsu, Takehiko; Matsuda, Kenichi; Nagaoka, Hiroto; Tsukamoto, Koji; Tanaka, Tetsuaki Organic Letters, 2007 , vol. 9, # 24 p. 5115 - 5118

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Citation Number: 28

Abstract

A new carbamoylation of tertiary amines is reported. This rare CH transformation features the direct generation of α-aminoalkyl radicals from tertiary amines, followed by the addition of the resultant nucleophilic radicals to isocyanates, enabling unique access to N, N- dialkylated amino acid derivatives. The authors put forward a mechanistic proposal that is based on the isolation of borinamides produced by capturing nitrogen radical ...