Controllable Rh(III)-Catalyzed Annulation between Salicylaldehydes and Diazo Compounds: Divergent Synthesis of Chromones and Benzofurans

• DOI: 10.1021/acs.orglett.6b03355
• Publication Date: 2016-12-01T19:51:49Z
• Authors: Peng Sun; Shang Gao; Chi Yang; Songjin Guo; Aijun Lin; Hequan Yao
• Keywords: Annulation; Decarbonylation; Benzofuran; Tandem; Chemoselectivity

A Rh(III)-catalyzed annulation between salicylaldehydes and diazo compounds with controllable chemoselectivity is described. AgNTf2 favored benzofurans via a tandem C–H activation/decarbonylation/annulation process, while AcOH led to chromones through activation/annulation pathway. The reaction exhibited good functional group tolerance scalability. Moreover, only single regioisomer of benzofuran was obtained due the in situ decarbonylation orientation effect.