Cobalt-Catalyzed Hydroacylative Dimerization of Allenes Leading to Skipped Dienes

Wei Ding, Yan King Terence Ho, Yasuhiro Okuda, Christopher Kevin Wijaya, Zheng Hao Tan, Naohiko Yoshikai

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

A cobalt-diphosphine catalyst has been found to promote a selective 1:2 coupling reaction between aldehydes and allenes to form β,δ-dialkylidene ketones, featuring skipped diene moieties, with high regioselectivities and stereoselectivities. The reaction is distinct from previously reported, rhodium-catalyzed aldehyde-allene 1:2 coupling to afford β,γ-dialkylidene ketones bearing 1,3-diene moieties. The present hydroacylative dimerization involves a unique allene/allene oxidative cyclization mode to form a C1-C2 linkage between the allene molecules.

Original languageEnglish
Pages (from-to)6173-6178
Number of pages6
JournalOrganic letters
Volume21
Issue number15
DOIs
Publication statusPublished - 2019 Aug 2
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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