Iodotrifluoromethylation of Alkenes and Alkynes with Sodium Trifluoromethanesulfinate and Iodine Pentoxide

Zhaojia Hang, Zejiang Li and Zhong-Quan Liu*

*State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China, Email: liuzhqlzu.edu.cn

Z. Hang, Z. Li, Z.-Q. Liu, Org. Lett., 2014, 16, 3648-3651.

DOI: 10.1021/ol501380e

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Abstract

Sodium trifluoromethanesulfinate and iodine pentoxide as safe solid reagents enable a scalable, selective, and convenient iodotrifluoromethylation of a wide range of alkenes and alkynes in aqueous medium. Mechanistic studies confirm a free-radical processes, in which key radical intermediates such as CF₃ and β-CF₃ alkyl radicals have been detected by spin trapping and electron spin resonance.

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Key Words

trifluoromethylation, iodination

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ID: J54-Y2014