Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates

James Z. Deng*, Daniel V. Paone*, Anthony T. Ginnetti, Hideki Kurihara, Spencer D. Dreher, Steven A. Weissman, Shaun R. Stauffer and Christopher S. Burgey

*Department of Medicinal Chemistry, Merck Research Laboratories, P.O. Box 4, West Point, Pennsylvania 19486, Email: james_dengmerck.com, daniel_paonemerck.com

J. Z. Deng, D. V. Paone, A. T. Ginnetti, H. Kurihara, S. D. Dreher, S. A. Weissman, S. R. Stauffer, C. S. Burgey, Org. Lett., 2009, 11, 345-347.

DOI: 10.1021/ol802556f

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Abstract

Suzuki reactions of electron-deficient 2-heterocyclic boronates generally give low conversions and remain challenging. A successful copper(I) facilitated Suzuki coupling of 2-heterocyclic boronates is broad in scope and affords greatly enhanced yields of these notoriously difficult couplings. Furthermore, mechanistic investigations suggest a possible role of copper in the catalytic cycle.

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Key Words

Heterobiaryls, Pyridines, Suzuki Coupling

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ID: J54-Y2009-0240