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

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

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 characte...

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Veröffentlicht in:Journal of the American Chemical Society 2011-05, Vol.133 (18), p.6948-6951
Hauptverfasser: Velcicky, Juraj, Soicke, Arne, Steiner, Roland, Schmalz, Hans-Günther
Format: Artikel
Sprache:eng
Schlagworte:
Acetonitriles - chemical synthesis
Boronic Acids - chemistry
Bromides - chemistry
Catalysis
Isoxazoles - chemistry
Methylation
Palladium - chemistry
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Zusammenfassung: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja201743j