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

Research output: Contribution to journalArticle

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.

Bibliographical metadata

Original languageEnglish
Pages (from-to)354-358
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number1
Early online date29 Nov 2016
DOIs
StatePublished - 28 Dec 2016