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Cross-Coupling Reactions of Aromatic and Heteroaromatic Silanolates with Aromatic and Heteroaromatic Halides

Scott E. Denmark*, Russell C. Smith, Wen-Tau T. Chang and Joseck M. Muhuhi

*Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, Email: denmarkscs.uiuc.edu

S. E. Denmark, R. C. Smith, W.-T. T. Chang, J. M. Muhuhi, J. Am. Chem. Soc., 2009, 131, 3104-3118.

DOI: 10.1021/ja8091449 (free Supporting Information)


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Abstract

Alkali-metal salts of a large number of electron-rich, electron-poor, and sterically hindered aryl- and heteroarylsilanols undergo efficient cross-coupling with a wide range of aromatic bromides and chlorides under mild conditions. The critical feature for the success of these coupling reactions and their considerable scope is the use of bis(tri-tert-butylphosphine)palladium.


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Palladium-Catalyzed Cross-Coupling Reactions of Substituted Aryl(dimethyl)silanols

S. E. Denmark, M. H. Ober, Adv. Synth. Catal., 2004, 346, 1703-1715.


Key Words

Hiyama-Denmark Coupling, biaryls, benzofurans


ID: J48-Y2009-0690