α-Palladation of imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-allylimines to pyrroles

Zhiyuan Chen, Beili Lu, Zhenhua Ding, Ke Gao, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

51 Citations (Scopus)

Abstract

We report here a palladium(II)-catalyzed oxidative cyclization reaction of N-allylimines derived from methyl ketones, typically acetophenones, affording pyrrole derivatives at room temperature under oxygen atmosphere. The reaction likely proceeds through α-palladation of the imine followed by olefin migratory insertion and β-hydride elimination, thus representing a new example of aerobic dehydrogenative Heck cyclization.

Original languageEnglish
Pages (from-to)1966-1969
Number of pages4
JournalOrganic letters
Volume15
Issue number8
DOIs
Publication statusPublished - 2013 Apr 19
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'α-Palladation of imines as entry to dehydrogenative heck reaction: Aerobic oxidative cyclization of N-allylimines to pyrroles'. Together they form a unique fingerprint.

Cite this