Recent Advances in Photoinduced Perfluoroalkylation Using Perfluoroalkyl Halides as the Radical Precursors

Abstract

Perfluoroalkylation is one of the most important methods for the introduction of multiple fluorine atoms into organic molecules in a single step. The use of photoinduced technology is a common strategy that uses the outstanding oxidation or reduction ability of a photo­redox catalyst in its excited state to generate perfluoroalkyl radicals from perfluoroalkyl halides. The perfluoroalkyl radicals thus obtained can undergo various subsequent reactions under mild conditions, such as ATRA reaction of alkenes, alkynes, and 1,n-enynes; carbo/heteroperfluoroalkylation of alkenes and isocyanides; and C–H/F perfluoroalkyl­ation. This allows the expedient incorporation of various perfluoroalkyl groups into the molecular motifs. Perfluorinated functional groups are still in demand in pharmaceutical and material sciences; this short review discusses recent advances in photoinduced perfluoroalkylation methodologies and technologies.

1 Introduction

2 Photocatalytic Perfluoroalkylation of Alkenes, Alkynes, and 1,n- Enynes

3 Photocatalytic Carboperfluoroalkylation or Heteroperfluoro­alkylation of Alkenes, Alkynes, Isocyanides, and Hydrazones

4 Photocatalytic ATRE Reactions of Alkenes with Perfluoroalkyl Halides­

5 Photocatalytic C–X (X = H, F) Bond Perfluoroalkylation

6 Continuous Flow Strategies in Photocatalytic Perfluoroalkylation

7 Conclusions

Key words

perfluoroalkylation - perfluoroalkyl halides - alkenes and alkynes - photoredox catalysis - ATRA reactions - carbo/heteroperfluoroalkylation - C–H perfluoroalkylation

Publication History

Received: 30 October 2021

Accepted after revision: 20 December 2021

Article published online:
21 February 2022

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