One-Pot Synthesis of Arylboronic Acids and Aryl Trifluoroborates by Ir-Catalyzed Borylation of Arenes

Jaclyn M. Murphy, C. Christoph Tzschucke and John F. Hartwig*

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

J. M. Murphy, C. C. Tzschucke, J. F. Hartwig, Org. Lett., 2007, 9, 757-760.

DOI: 10.1021/ol062903o

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Abstract

Arylboronic acids and aryl trifluoroborates are synthesized in a one-pot sequence by Ir-catalyzed borylation of arenes. To prepare the arylboronic acids, the Ir-catalyzed borylation is followed by oxidative cleavage of the pinacol boronates with NaIO₄. To prepare the aryltrifluoroborate, the Ir-catalyzed borylation is followed by displacement of pinacol by KHF₂.

see article for more examples

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A C-H Borylation Approach to Suzuki-Miyaura Coupling of Typically Unstable 2-Heteroaryl and Polyfluorophenyl Boronates

D. W. Robbins, J. F. Hartwig, Org. Lett., 2012, 14, 4266-4269.

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Key Words

Arylboronic Acids, Aryltrifluoroborates, Sodium Periodate

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ID: J54-Y2007-0680