Palladium-Catalyzed anti-Michael Reductive Heck Reaction of α,β-Unsaturated Esters

Tao Guo, Yalan Ding, Lili Zhou, Haiyan Xu, Teck Peng Loh, Xiaojin Wu

Research output: Contribution to journalArticlepeer-review

39 Scopus citations

Abstract

A general intermolecular anti-Michael reductive Heck reaction of α,β-unsaturated esters with organobromides has been developed. Most topical classes of aryl, heteroaryl, and vinyl bromides were found to efficiently react with a variety of internal conjugated alkenes. This protocol set up a platform toward diverse α-arylated 1,6-dicarbonyl frameworks found in natural products and drugs, which are still highly challenging targets in traditional α-arylation protocols because of competitive selectivity of enolation. A removable directing group, gram-scale reaction, and modification of complex molecules have additionally demonstrated that the anti-Michael reductive Heck reaction is a powerful complementary strategy to the classical α-arylation approaches. Preliminary mechanistic studies are consistent with our proposed mechanistic design.

Original languageEnglish
Pages (from-to)7262-7268
Number of pages7
JournalACS Catalysis
Volume10
Issue number13
DOIs
StatePublished - 2 Jul 2020

Keywords

  • 1,6-dicarbonyl frameworks
  • anti-Michael selectivity
  • palladacycle
  • reductive Heck reaction
  • removable directing group
  • α-arylation

Fingerprint

Dive into the research topics of 'Palladium-Catalyzed anti-Michael Reductive Heck Reaction of α,β-Unsaturated Esters'. Together they form a unique fingerprint.

Cite this