Gold-catalyzed dual C-C bond cleavage of biphenylenes bearing a pendant alkyne at ambient temperature

Hideaki Takano, Sari Okazaki, Shun Nishibe, Takeharu Ito, Natsumi Shiozawa, Natsuhiko Sugimura, Kyalo Stephen Kanyiva, Takanori Shibata

Research output: Contribution to journalArticlepeer-review

Abstract

We report a catalytic skeletal rearrangement of biphenylenes with a pendant alkyne moiety at room temperature by a cationic gold catalyst, which involves the cleavage of two bonds: the C-C bond of biphenylene and the C(sp)-C(sp2 or sp3) bond. Experimental and theoretical studies revealed that the reaction mechanism included π-activation of the alkyne, ring expansion and 1,2-carbon shift.

Original languageEnglish
Pages (from-to)5826-5831
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number30
DOIs
Publication statusPublished - 2020 Aug 14

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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