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

Peng Sun, Shang Gao, Chi Yang, Songjin Guo, Aijun Lin* and Hequan Yao*

*State Key Laboratory of Natural Medicines (SKLNM) and Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing 210009, P. R. China, Email: ajlincpu.edu.cn, hyaocpu.edu.cn

P. Sun, S. Gao, C. Yang, S. Guo, A. Lin, H. Yao, Org. Lett., 2016, 18, 6464-6467.

DOI: 10.1021/acs.orglett.6b03355

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Abstract

A Rh(III)-catalyzed annulation between salicylaldehydes and diazo compounds offers good functional group tolerance, scalability, and a controllable chemoselectivity. AgNTf₂ as additive favored benzofurans via a tandem C-H activation/decarbonylation/annulation process, while AcOH led to chromones through a C-H activation/annulation pathway.

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Key Words

benzofurans, chromones

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ID: J54-Y2016