Silver-Mediated Intermolecular [2 + 2 + 1] Cyclization of Terminal Alkynones with Elemental Selenium: Regioselective Synthesis of 2,4- or 3,4-Dicarbonylselenophenes

  • Peng He
  • , Ye Wang
  • , Yingge Gu
  • , Lu Cheng
  • , Yilin Zhu
  • , Chengyu Wang*
  • , Yanzhong Li*
  • *Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient and atom-economical silver-mediated [2 + 2 + 1] cyclization protocol for the selective synthesis of 2,4- or 3,4-dicarbonylselenophenes has been developed. Readily accessible substrates, commercially available elemental selenium, and good functional group tolerance make this procedure attractive for the selective synthesis of dicarbonylselenophenes. Preliminary mechanistic investigations indicated that silver acetylene species are possible intermediates for the formation of 3,4-dicarbonylselenophenes.

Original languageEnglish
Pages (from-to)14978-14988
Number of pages11
JournalJournal of Organic Chemistry
Volume88
Issue number21
DOIs
StatePublished - 3 Nov 2023

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