Regioselective Cycloaddition and Substitution Reaction of Tertiary Propargylic Alcohols and Heteroareneboronic Acids via Acid Catalysis

Jian Fei Bai, Jianbo Tang, Xiaolong Gao, Zhi Jiang Jiang, Bencan Tang, Jia Chen, Zhanghua Gao

Research output: Journal PublicationArticlepeer-review

Abstract

We report an acid-catalyzed formal cycloaddition and dehydrative substitution reaction of tertiary propargylic alcohols and heteroareneboronic acids. The properties of the substituents on the alkynyl moiety determines the regioselectivity of the reaction, which could selectively construct fused heterocycles, tetrasubstituted allenes, or 1,3-dienes. This reaction proceeds efficiently with a wide array of substrate scope in up to 89% yield. A significant advantage of this protocol is the transition-metal-free and mild conditions needed. 2022 American Chemical Society.

Original languageEnglish
Pages (from-to)4507-4512
Number of pages6
JournalOrganic Letters
Volume24
Issue number25
DOIs
Publication statusPublished - 1 Jul 2022

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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