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

32 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

Fingerprint

Isocyanates
Carbon Cycle
isocyanates
Amines
resources
amines
Carbon
Mepivacaine
carbon
Local Anesthetics
anesthetics
Nitrogen
Derivatives
Amino Acids
amino acids
proposals
isolation
nitrogen

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Radical fixation of functionalized carbon resources : α-sp 3C - H carbamoylation of tertiary amines with aryl isocyanates. / Yoshimitsu, Takehiko; Matsuda, Kenichi; Nagaoka, Hiroto; Tsukamoto, Koji; Tanaka, Tetsuaki.

In: Organic Letters, Vol. 9, No. 24, 22.11.2007, p. 5115-5118.

Research output: Contribution to journalArticle

Yoshimitsu, Takehiko ; Matsuda, Kenichi ; Nagaoka, Hiroto ; Tsukamoto, Koji ; Tanaka, Tetsuaki. / Radical fixation of functionalized carbon resources : α-sp 3C - H carbamoylation of tertiary amines with aryl isocyanates. In: Organic Letters. 2007 ; Vol. 9, No. 24. pp. 5115-5118.
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