Synthesis of 1H-isoindoliums by electrophile-mediated cascade cyclization/iodination of propargylamine-based 1,6-diynes

Jian Fang Cui, Qiong Yu, O. Wa-Yi, Li Wu Huang, Bin Yang, Man Kin Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

Abstract

A highly regio- and chemoselective synthesis of 1H-isoindoliums through a facile and novel cascade cyclization reaction of propargylamine-based 1,6-diynes under mild conditions has been developed. Different functional groups were compatible under the optimized reaction conditions, giving the corresponding products in up to 94% yields. Upon treatment with a base, the alkyne moiety of 1H-isoindoliums could be further transformed to allenes in excellent yields.

Original languageEnglish
Pages (from-to)3755-3762
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume20
Issue number18
DOIs
Publication statusPublished - 7 Apr 2022

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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