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

Daniel W. Robbins and John F. Hartwig*

*University of California, Department of Chemistry, Berkeley, California 94720, United States, Email: jhartwigberkeley.edu

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

DOI: 10.1021/ol301570t (free Supporting Information)



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Abstract

Pinacol boronate esters that are analogous to unstable boronic acids are formed in high yield by iridium-catalyzed C-H borylation of heteroarenes and fluoroarenes. These boronates are stable in the solid state or in solution and can be generated and used in situ for the palladium-catalyzed synthesis of biaryls and heterobiaryls from arenes and haloarenes.

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

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


Key Words

heterobiaryls


ID: J54-Y2012-2670