Rh(iii)-catalyzed direct C-H/C-H cross-coupling of quinones with arenes assisted by a directing group: Identification of carbazole quinones as GSKβ inhibitors

Abstract

Rh-catalyzed direct C-H/C-H cross-coupling reaction of various (hetero)arenes with quinones is developed. This protocol is effective for a broad range of both quinone and arene substrates and a wide range of directing groups for this reaction, affording structurally diverse aryl-substituted quinones with high synthetic utility. Moreover, the present synthetic route allowed for the rapid construction of the carbazole quinone moiety that was identified as a new inhibitor scaffold for GSKβ. This journal is © The Royal Society of Chemistry 2015