Photoredox-Catalyzed α-Sulfonylation of Ketones from Sulfur Dioxide and Thianthrenium Salts

He, Fu‐Sheng; Bao, Ping; Tang, Zhimei; Yu, Feiyan; Deng, Wei‐Ping; Wu, Jie

doi:10.1021/acs.orglett.2c01132

Cited by 47 publications

(24 citation statements)

References 71 publications

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“…The methyl ester derivative of dicamba, a broad spectrum herbicide, and aniracetam, an AMPA receptor modulator, delivered both cyclic and acyclic amine-based dithiocarbamates in moderate yield (45 and 53%, respectively). He, Wu and co-workers devised a three-component coupling protocol between aryl and alkyl thiathrenium salts ( 77.1 , generated via thianthration of alcohols), 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct ( 77.3 , DABCO·(SO 2 ) 2 ) and silyl enol ethers ( 77.2 ) (Scheme A) . As outlined Scheme B, thianthrenium salts ( 77.1 ) can undergo single-electron reduction from the photoexcited * Ir(ppy) 3 , generating aryl radical species (analogously to Scheme ).…”

Section: Late-stage Aromatic C(sp2)–h Functionalizationmentioning

confidence: 99%

Photocatalytic Late-Stage C–H Functionalization

et al. 2023

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The emergence of modern photocatalysis, characterized by mildness and selectivity, has significantly spurred innovative late-stage C–H functionalization approaches that make use of low energy photons as a controllable energy source. Compared to traditional late-stage functionalization strategies, photocatalysis paves the way toward complementary and/or previously unattainable regio- and chemoselectivities. Merging the compelling benefits of photocatalysis with the late-stage functionalization workflow offers a potentially unmatched arsenal to tackle drug development campaigns and beyond. This Review highlights the photocatalytic late-stage C–H functionalization strategies of small-molecule drugs, agrochemicals, and natural products, classified according to the targeted C–H bond and the newly formed one. Emphasis is devoted to identifying, describing, and comparing the main mechanistic scenarios. The Review draws a critical comparison between established ionic chemistry and photocatalyzed radical-based manifolds. The Review aims to establish the current state-of-the-art and illustrate the key unsolved challenges to be addressed in the future. The authors aim to introduce the general readership to the main approaches toward photocatalytic late-stage C–H functionalization, and specialist practitioners to the critical evaluation of the current methodologies, potential for improvement, and future uncharted directions.

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Section: Late-stage Aromatic C(sp2)–h Functionalizationmentioning

confidence: 99%

Photocatalytic Late-Stage C–H Functionalization

et al. 2023

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“…Therefore, exploration of novel and easily accessible radical precursors for the construction of diverse sulfones is still highly desirable. In 2022, Wu and coworkers reported that thianthrenium salts 23 prepared from thianthrene ( S )‐oxides (TTO) were compatible with the three‐component sulfonylation of silyl enol ethers 12 under blue light [31] . Notably, aryl and alkyl thianthrenium salts were both tolerated, producing a variety of α ‐sulfonated ketones 24 (Figure 13).…”

Section: Dabso‐involved Multicomponent Sulfonylation Reactionsmentioning

confidence: 99%

Multicomponent Reactions Based on SO₂ Surrogates: Recent Advances

Chen

Lian

2023

Eur J Org Chem

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Compounds containing sulfonyl-derived functional groups have received intensive attention owing to their widespread applications in life science, pharmaceuticals and materials science. To access this type of compounds, the multi-component sulfonylation reactions relying on sulfur dioxide (SO 2 ) insertion strategy have emerged as novel and attractive approaches in the past decade. The utilization of SO 2 surrogates for SO 2 insertion in the multicomponent reactions (MCRs) have improved reaction flexibility and step economy. Moreover, some advances have been achieved in the challenging but practical asymmetric MCRs for the construction of high value-added chiral sulfones. This review aims to summarize the progress made in the MCRs involving SO 2 surrogates from 2019 to 2022, and point out the potentials and challenges in this field.

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“…Proposed mechanism shows that sulfinate anion combined with aryl thianthrenium salts (1) In 2022, Wu reported an efficient photocatalytic sulfonation of silyl enol ethers with DABCO•(SO 2 ) 2 and organothianthrenium salts, providing a variety of β-keto sulfones in medium to good yields (Scheme 23). 89 Both aryl and alkyl thianthrenium salts were tolerated in the reaction. Proposed mechanism showed that photoexcited Ir III* reduced organothianthrenium salts to form radical species and oxidized photocatalyst Ir IV via SET.…”

Section: Please Do Not Adjust Marginsmentioning

confidence: 99%