Ru(OAc)₃-Catalyzed Regioselective Difunctionalization of Alkynes: Access to (E)-2-Bromo-1-alkenyl Sulfonates

Lu Chen*, Ya Li, Xiaoyan Bai, Dian Dong, Meiwei Pan, Ling Huang, Runqin Huang, Xiaotong Long and Yibiao Li*

*School of Biotechnology and Health Science, Wuyi University, Jiangmen 529020, China, Email: wyuchemcl126.com, leeyib268126.com

L. Chen, Y. Li, X. Bai, D. Dong, M. Pan, L. Huang, R. Huang, X. Long, Y. Li, Org. Lett., 2023, 25, 7025-7029.

DOI: 10.1021/acs.orglett.3c02623

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Abstract

Ruthenium(III) acetate catalyzes a regioselective synthesis of (E)-2-bromo-1-phenylvinyl trifluoromethanesulfonates through alkyne difunctionalization in the presence of N-bromosuccinimide (NBS) and trimethylsilyl trifluoromethanesulfonate (TMSOTf). The protocol tolerates a broad range of functional groups.

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proposed mechanism

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Key Words

alkenyl bromides, protected enols, NBS, multicomponent reactions

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ID: J54-Y2023