Metal-Free Iodoperfluoroalkylation: Photocatalysis versus Frustrated Lewis Pair Catalysis

Lucas Helmecke; Michael Spittler; Bernd M. Schmidt; Constantin Czekelius

doi:10.1055/s-0040-1707232

Synthesis, Table of Contents

Synthesis 2021; 53(01): 123-134
DOI: 10.1055/s-0040-1707232

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Metal-Free Iodoperfluoroalkylation: Photocatalysis versus Frustrated Lewis Pair Catalysis

Lucas Helmecke

,

Michael Spittler

,

Bernd M. Schmidt

,

Constantin Czekelius ∗

Institute for Organic Chemistry and Macromolecular Chemistry, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf, Germany Email: constantin.czekelius@hhu.de

› Author Affiliations

Abstract

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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.

Key words

iodoperfluoroalkylation - frustrated Lewis pair - electron donor–acceptor complex - halogenations - radicals

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References

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