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

Velcicky, Juraj and Soicke, Arne and Steiner, Roland and Schmalz, Hans-Günther (2011) Palladium-Catalyzed Cyanomethylation of Aryl Halides through Domino Suzuki Coupling-Isoxazole Fragmentation. Journal of the American Chemical Society, 133 (18). pp. 6948-6951. ISSN 1520-5126

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.

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Date Deposited: 18 May 2011 23:45
Last Modified: 18 May 2011 23:45
URI: https://oak.novartis.com/id/eprint/5085

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