Pinacol boronates by direct arene borylation with borenium cations

Alessandro Del Grosso, Paul J. Singleton, Christopher A. Muryn, Michael J. Ingleson

Research output: Contribution to journalArticlepeer-review

Abstract

Borenium does it direct: A boron analogue of the Friedel-Crafts reaction uses inexpensive catecholatoborenium cations that are sufficiently electrophilic to borylate arenes by electrophilic aromatic substitution. The direct arene borylation proceeds with high regioselectivity for a range of anilines, N-heterocycles, and thiophenes. Subsequent one-pot transesterification provides the synthetically useful pinacol boronate esters (see scheme).

Original languageEnglish
Pages (from-to)2102-2106
Number of pages5
JournalAngewandte Chemie - International Edition
Volume50
Issue number9
DOIs
Publication statusPublished - 25 Feb 2011

Keywords

  • borenium ions
  • borocations
  • boronate esters
  • borylation
  • electrophilic substitution

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