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Palladium-catalyzed Cyanomethylation of Aryl Halides Through Domino Suzuki Coupling-Isoxazole Fragmentation

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

J Am Chem Soc. 2011 May 11;133(18):6948-51.

PMID: 21504197

Abstract:

A one-pot protocol for the cyanomethylation of aryl halides through a palladium-catalyzed reaction with isoxazole-4-boronic acid pinacol ester was developed. Mechanistically, the reaction proceeds through (1) Suzuki coupling, (2) base-induced fragmentation, and (3) deformylation as shown by characterization of all postulated intermediates. Under optimized conditions (PdCl(2)dppf, KF, DMSO/H(2)O, 130 °C) a broad spectrum of aryl bromides could be converted into arylacetonitriles with up to 88% yield.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
LS7931218 isoxazole-4-boronic acid isoxazole-4-boronic acid Price
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