Synthesis 2021; 53(01): 123-134
DOI: 10.1055/s-0040-1707232
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© Georg Thieme Verlag Stuttgart · New York

Metal-Free Iodoperfluoroalkylation: Photocatalysis versus Frustrated Lewis Pair Catalysis

Lucas Helmecke
,
Michael Spittler
,
,
Institute for Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany   Email: constantin.czekelius@hhu.de
› Author Affiliations
This research was funded by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) (Grant No. 396890929/GRK 2482). The generous support provided to M. Spittler through a fellowship provided by the Studienstiftung des deutschen Volkes (Doktorandenstipendium) is most gratefully acknowledged.
Further Information

Publication History

Received: 11 May 2020

Accepted after revision: 30 June 2020

Publication Date:
12 August 2020 (online)


In memoriam Professor Rolf Huisgen

Abstract

A comparison of two catalytic, metal-free iodoperfluoro­alkylation protocols is presented. Frustrated Lewis pairs [ t Bu3P/B(C6F5)3] or phosphines/phosphites under visible light irradiation efficiently mediate the functionalization of non-activated alkenes and alkynes. A comprehensive account of the corresponding substrate scopes as well as insights into the mechanistic details of both reaction pathways are provided.

Supporting Information

 
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