Photoredox Catalysis in C–S Bond Construction: Recent Progress in Photo‐Catalyzed Formation of Sulfones and Sulfoxides

Abstract

The emergence of radical chemistry as well as green chemistry in organic synthesis has initiated an interest in photochemistry over the past decade. With catalytic amounts of photoredox catalysts under light irradiation, high active radical species are produced, which could trigger the subsequent organic transformations smoothly. Among the various photoredox reactions, photo‐catalytic C–S bond formation continues to thrive, as the C–S bond is indispensable in many important biological and pharmaceutical compounds. Great attention has been devoted to this area as illustrated by the series of papers on sulfone and sulfoxide skeleton synthesis under irradiation published in the past years. This review summarizing the recent advances in photo‐catalyzed sulfones and sulfoxide formation is arranged by reaction type together with the sulfur source covering sulfonylation and sulfinylation reactions. It is intended to provide readers with a comprehensive understanding of photo‐catalytic C‐S bond formation and offer help for future research.

A chiral nickel DBFOX complex as a bifunctional catalyst for visible-light-promoted asymmetric photoredox reactions

“…Visible light photoredox catalysis has emerged as a powerful strategy for organic synthesis. 1 However, the development of catalytic asymmetric photoredox reactions is still highly desirable and remains a formidable challenge owing to the difficulties in controlling the stereochemistry of highly reactive intermediates such as radicals and radical ions. 2 , 3 Pioneering work by Sibi, Porter, and others has demonstrated that transition-metal-based chiral Lewis acids are capable of governing the enantioselective conjugate addition of radicals produced by stoichiometric reduction of organic halides ( Fig.…”

Radical Reactions for the Synthesis of 3‐Substituted Chroman‐4‐ones

“…In the past decade, visible-light promoted organic synthesis has emerged as a highly economical and eco-friendly strategy for the construction of various chemical bonds under mild conditions. [94][95][96][97][98][99][100][101][102][103][104][105] Particularly, visible-light photoredox catalysis is an ideal tool to initiate radical cascade reactions for the synthesis of heterocycles. [106][107][108][109][110][111][112][113][114][115][116][117][118] In 2017, Hong's group reported a visible-light-enabled radical strategy to synthesize spiroepoxy chroman-4-one derivatives 74 via a tandem oxidation/radical cyclization/epoxidation process (Scheme 14).…”

Selectivity control in thiol–yne click reactions via visible light induced associative electron upconversion

“…[9][10][11] Visible light photoredox catalysis has evolved into an important method in organic chemistry and can provide superior reaction conditions. [12][13][14][15] The rst example of a photoredox thiol-yne click reaction under metal-free conditions with good yields and selectivity for b-vinylsuldes was reported in 2016. 16 Later, Wang and co-workers reported a photoredox process driven by 1 mol% mesityl-10-methyl-acridinium tetra-uoroborate, providing a range of mono-and bis-substituted sulde products.…”