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

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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

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Most cited references 47

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Organic Photoredox Catalysis.

Nathan Romero, David Nicewicz (2016)

In this review, we highlight the use of organic photoredox catalysts in a myriad of synthetic transformations with a range of applications. This overview is arranged by catalyst class where the photophysics and electrochemical characteristics of each is discussed to underscore the differences and advantages to each type of single electron redox agent. We highlight both net reductive and oxidative as well as redox neutral transformations that can be accomplished using purely organic photoredox-active catalysts. An overview of the basic photophysics and electron transfer theory is presented in order to provide a comprehensive guide for employing this class of catalysts in photoredox manifolds.

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Visible light-mediated atom transfer radical addition via oxidative and reductive quenching of photocatalysts.

Carl-Johan Wallentin, John D Nguyen, Peter Finkbeiner … (2012)

Herein, the development of visible light-mediated atom transfer radical addition (ATRA) of haloalkanes onto alkenes and alkynes using the reductive and oxidative quenching of [Ir{dF(CF(3))ppy}(2)(dtbbpy)]PF(6) and [Ru(bpy)(3)]Cl(2) is presented. Initial investigations indicated that the oxidative quenching of photocatalysts could effectively be utilized for ATRA, and since that report, the protocol has been expanded by broadening the scope of the reaction in terms of the photocatalysts, substrates, and solvents. In addition, further modifications of the reaction conditions allowed for the efficient ATRA of perfluoroalkyl iodides onto alkenes and alkynes utilizing the reductive quenching cycle of [Ru(bpy)(3)]Cl(2) with sodium ascorbate as the sacrificial electron donor. These results signify the complementary nature of the oxidative and reductive quenching pathways of photocatalysts and the ability to predictably direct reaction outcome through modification of the reaction conditions.