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Metal-Free Activation of C-I Bonds and Perfluoroalkylation of Alkenes with Visible Light Using Phosphine Catalysts

Lucas Helmecke, Michael Spittler, Kai Baumgarten and Constantin Czekelius*

*Institute of Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany, Email: constantin.czekeliusuni-duesseldorf.de

L. Helmecke, M. Spittler, K. Baumgarten, C. Czekelius, Org. Lett., 2019, 21, 7804-7808.

DOI: 10.1021/acs.orglett.9b02812 (free Supporting Information)


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Abstract

The use of catalytic amounts of phosphines and blue light irradiation enables an efficient metal-free, iodo perfluoroalkylation of olefins under mild conditions within short reaction times. The reaction presumably proceeds upon generation of perfluoroalkyl radicals, which are formed by catalyst-induced absorption enhancement.

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Key Words

perfluoroalkylation, iodination, photochemistry


ID: J54-Y2019