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Radical fixation of functionalized carbon resources: alpha-sp3C-H carbamoylation of tertiary amines with aryl isocyanates

Radical fixation of functionalized carbon resources: alpha-sp3C-H carbamoylation of tertiary amines with aryl isocyanates

Organic Letters 9(24): 5115-5118

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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Accession: 055345849

Download citation: RISBibTeXText

PMID: 17975923

DOI: 10.1021/ol7023295

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