Copper and Zinc Copromoted Bromo(chloro)trifluoromethylation of Alkenes and Alkynes with Trifluoromethanesulfonic Anhydride

Yao Ouyang, Chao-Lai Tong, Xiu-Hua Xu and Feng-Ling Qing*

*Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China, Email: flqmail.sioc.ac.cn

Y. Ouyang, C.-L. Tong, X.-H. Xu, F.-L. Qing, Org. Lett., 2021, 23, 346-350.

DOI: 10.1021/acs.orglett.0c03855

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Abstract

A trifluoromethylation of alkenes or alkynes using trifluoromethanesulfonic anhydride (Tf2O) as a trifluoromethylating reagent in the presence of CuX₂ (X = Br, Cl), Zn powder, and 2,2'-bipyridine affords bromo(chloro)trifluoromethylated products in good yields. CuX₂ plays a dual role as the catalyst and halide source, whereas 2,2′-bipyridine acts as both the activation reagent and ligand.

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Key Words

trifluoromethylation, bromination

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ID: J54-Y2021