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

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 (PdCl₂dppf, KF, DMSO/H₂O, 130 °C) a broad spectrum of aryl bromides could be converted into arylacetonitriles with up to 88% yield.

https://pubs.acs.org/doi/abs/10.1021/ja201743j