Radical fixation of functionalized carbon resources: α-sp 3C - H carbamoylation of tertiary amines with aryl isocyanates

Takehiko Yoshimitsu, Kenichi Matsuda, Hiroto Nagaoka, Koji Tsukamoto, Tetsuaki Tanaka

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

A new carbamoylation of tertiary amines is reported. This rare C - H 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 intermediates with Et3B. The present transformation provides a novel one-step process for producing mepivacaine, a clinically important local anesthetic, from readily available materials.

Original languageEnglish
Pages (from-to)5115-5118
Number of pages4
JournalOrganic Letters
Volume9
Issue number24
DOIs
Publication statusPublished - Nov 22 2007
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Radical fixation of functionalized carbon resources: α-sp <sup>3</sup>C - H carbamoylation of tertiary amines with aryl isocyanates'. Together they form a unique fingerprint.

  • Cite this