BCl3-Induced Annulative Oxo- and Thioboration for the Formation of C3-Borylated Benzofurans and Benzothiophenes

Andrew J. Warner, Anna Churn, John S. McGough, Michael J. Ingleson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

BCl3-induced borylative cyclization of aryl-alkynes possessing ortho-EMe (E=S, O) groups represents a simple, metal-free method for the formation of C3-borylated benzothiophenes and benzofurans. The dichloro(heteroaryl)borane primary products can be protected to form synthetically ubiquitous pinacol boronate esters or used in situ in Suzuki–Miyaura cross couplings to generate 2,3-disubstituted heteroarenes from simple alkyne precursors in one pot. In a number of cases alkyne trans-haloboration occurs alongside, or instead of, borylative cyclization and the factors controlling the reaction outcome are determined.

Original languageEnglish
Pages (from-to)354-358
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number1
DOIs
Publication statusPublished - 29 Nov 2016

Keywords

  • annulation
  • borylation
  • cross coupling
  • electrophilic cyclization
  • organoboranes

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