Palladium-Catalysed Cross Coupling of Arylboronic Acids with 2-Chloro-1,4-naphthoquinones: the Synthesis of 2-Aryl- and 2,3-Bisaryl-1,4-naphthoquinones

Wayne M. Best, Wayne M. Best, Colette G. Sims, Colette G. Sims, Merilyn Winslade and Merilyn Winslade

Abstract

2-Chloro-1,4-naphthoquinones underwent palladium-catalysed cross coupling reactions with arylboronic acids to give the corresponding 2-aryl-1,4-naphthoquinones. Similarly, 2,3-dichloro-1,4-naphthoquinone underwent efficient cross coupling reactions with arylboronic acids to give mono or bis adducts. The required 2-chloro-1,4-naphthoquinones were conveniently prepared from the corresponding 2-hydroxy-1,4-naphthoquinones by treatment with oxalyl chloride.

Australian Journal of Chemistry 54(6) 401 - 404 (2001) doi:10.1071/CH01024