Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates
Organic Letters2008Vol. 11(2), pp. 345–347
Citations Over TimeTop 10% of 2008 papers
James Z. Deng, Daniel V. Paone, Anthony T. Ginnetti, Hideki Kurihara, Spencer D. Dreher, Steven A. Weissman, Shaun R. Stauffer, Christopher S. Burgey
Abstract
The palladium-catalyzed Suzuki-Miyaura reaction has been utilized as one of the most powerful methods for C-C bond formation. However, Suzuki reactions of electron-deficient 2-heterocyclic boronates generally give low conversions and remain challenging. The successful copper(I) facilitated Suzuki coupling of 2-heterocyclic boronates that is broad in scope is reported. Use of this methodology 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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