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, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, and Department of Chemistry, University of Illinois, 600 South Matthews Avenue, Urbana, Illinois 61801
Org. Lett., 2007, 9 (5), pp 757–760
DOI: 10.1021/ol062903o
Publication Date (Web): February 3, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jhartwig@uiuc.edu

Abstract

Abstract Image

The synthesis of arylboronic acids and aryl trifluoroborates in a one-pot sequence by Ir-catalyzed borylation of arenes is reported. To prepare the arylboronic acids, the Ir-catalyzed borylation is followed by oxidative cleavage of the boronic ester with NaIO4. To prepare the aryltrifluoroborate, the Ir-catalyzed borylation is followed by displacement of pinacol by KHF2. These two-step sequences give products that are more reactive toward subsequent chemistry than the initially formed pinacol boronates.

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History

  • Published In Issue March 01, 2007
  • Received November 30, 2006

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