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). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Original languageEnglish
    Pages (from-to)2102-2106
    Number of pages4
    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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