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  • Title: Radical fixation of functionalized carbon resources: alpha-sp3C-H carbamoylation of tertiary amines with aryl isocyanates.
    Author: Yoshimitsu T, Matsuda K, Nagaoka H, Tsukamoto K, Tanaka T.
    Journal: Org Lett; 2007 Nov 22; 9(24):5115-8. PubMed ID: 17975923.
    Abstract:
    A new carbamoylation of tertiary amines is reported. This rare C-H transformation features the direct generation of alpha-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 intermediates with Et3B. The present transformation provides a novel one-step process for producing mepivacaine, a clinically important local anesthetic, from readily available materials.
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