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Palladium-Catalyzed Cyanomethylation of Aryl Halides through Domino Suzuki Coupling-Isoxazole Fragmentation

Juraj Velcicky*, Arne Soicke, Roland Steiner and Hans-Günther Schmalz*

*Novartis Institutes for Biomedical Research, Forum 1, Novartis Campus, CH-4056 Basel, Switzerland, Email: juraj.velcickynovartis.com, schmalzuni-koeln.de

J. Velcicky, A. Soicke, R. Steiner, H.-G. Schmalz, J. Am. Chem. Soc., 2011, 133, 6948-6951.

DOI: 10.1021/ja201743j (free Supporting Information)


Abstract

A one-pot protocol for the cyanomethylation of aryl halides through a palladium-catalyzed reaction with isoxazole-4-boronic acid pinacol ester proceeds through Suzuki coupling, base-induced fragmentation, and deformylation. Under optimized conditions (PdCl2dppf, KF, DMSO/H2O, 130 °C) a broad spectrum of aryl bromides could be converted into arylacetonitriles in good yields.


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Key Words

α-Arylation, Cyanomethylation


ID: J48-Y2011-1380