Decarbonylative Borylation of Amides by Palladium Catalysis

Shicheng Shi, Michal Szostak

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

The development of transition-metal-catalyzed borylation reactions is of significant importance for the fields of organic synthesis and medicinal chemistry because of the versatility of organoboron functional groups. Herein, we report the direct decarbonylative borylation of amides by highly selective carbon-nitrogen bond cleavage by palladium catalysis. The approach capitalizes on the ground-state destabilization of the amide bond in N-acyl glutarimides to achieve Pd-catalyzed insertion into the amide N-C bond and decarbonylation (deamidation). Mechanistic studies and the utility of this methodology in orthogonal sequential cross-couplings of robust, bench-stable amides are reported.

Original languageEnglish (US)
Pages (from-to)4901-4907
Number of pages7
JournalACS Omega
Volume4
Issue number3
DOIs
StatePublished - Mar 5 2019

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

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