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DOI: 10.1055/s-2007-968425
Ir-Catalyzed Borylation and Sequential Functionalization of Arenes
Contributor(s):Paul Knochel, Andrei GavryushinYale University, New Haven and University of Illinois, Urbana, USA
Arenes to Anilines and Aryl Ethers by Sequential Iridium-Catalyzed Borylation and Copper-Catalyzed Coupling
Org. Lett. 2007, 9: 761-764
Publication History
Publication Date:
24 April 2007 (online)
Key words
borylation - iridium -
Significance
The Ir-catalyzed borylation of aromatic compounds represents a new useful method for the preparation of polyfunctionalized arylboronates, which have become extremely important intermediates in modern organic synthesis. This reaction is complementary to the usual preparation of arylboronic acids. It requires only a quite low amount of the Ir catalyst and usually offers excellent yields of products. If the resulting arylboron compounds are transformed into anilines and aryl ethers, this method presents a simple functionalization of an arene C-H bond.
Comment
This publication is a continuation of the previous article on this topic by the same group (J. M. Murphy, C. C. Tzschucke, J. F. Hartwig Org. Lett. 2007, 9, 757-760). The regioselectivity of the C-H borylation process is mostly determined by steric rather than electronic factors, and therefore offers a useful method for the preparation of 3-substituted arylboronic acids. The authors also reported a useful protocol for the conversion of pinacolborates into boronic acids and trifluoroborates, which are more preferable reagents for many applications.