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