Meta Halogenation of 1,3-Disubstituted Arenes via Iridium-Catalyzed Arene Borylation

Jaclyn M. Murphy, Xuebin Liao and John F. Hartwig*

*Department of Chemistry, University of Illinois, 600 South Matthews Avenue, Urbana, Illinois 61801-3602, Email: jhartwiguiuc.edu

J. M. Murphy, X. Liao, J. F. Hartwig, J. Am. Chem. Soc., 2007, 129, 15434-15435.

DOI: 10.1021/ja076498n

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Abstract

Iridium-catalyzed borylation of 1,3-disubstituted arenes with B₂pin₂, followed by reaction of the boronic ester with copper(II) bromide or chloride converts arylboronic esters to the corresponding meta-halogenated aryl halides. Various functional groups, such as alkoxy, alkyl, halogen, nitrile, ester, amide, and pivaloyl and TIPS-protected alcohols, are tolerated.

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Key Words

aryl bromides, aryl chlorides

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ID: J48-Y2007-4150