78114-06-4Relevant academic research and scientific papers
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
, p. 5115 - 5118 (2007)
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.
