Generation of sulfonated isobenzofuran-1(3<i>H</i>)-ones under photocatalysis through the insertion of sulfur dioxide

Zhang, Jun; Zhou, Kaida; Wu, Jie

doi:10.1039/c7qo00987a

Cited by 66 publications

(23 citation statements)

References 60 publications

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“…Jun Zhang and co‐workers reported the synthesis of sulfonated isobenzofuran‐1(3H)‐ones starting from 2‐vinyl benzoic acids, aryldiazonium salts, DABCO ⋅ (SO 2 ) 2 and Ir(ppy) 3 as the photocatalyst under visible light at room temperature (Scheme 49). [75] A variety of aryl diazonium salts were utilized to obtain the desired products in good yields. Similarly, vinyl benzoic acid derivatives bearing different substituents worked efficiently under these conditions to afford the expected sulfonated isobenzofuran‐1(3H)‐ones in excellent yields.…”

Section: C−s Bond Formationmentioning

confidence: 99%

Aryldiazonium Salts in Photoredox Catalysis – Recent Trends

et al. 2021

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Aryl diazonium salts are an important class of organic compounds that are now widely used as arylating agents in photoredox catalysis owing to their lower redox potential, broad substrate scope, and atom economy. They have successfully been used in many interesting organic transformations to introduce an aryl group. They serve as good alternatives for aryl halides and other aryl organometallic reagents primarily used as aryl group surrogates. New reactions using aryl diazonium salts are continually emerging, and in this review, we have highlighted some recent developments in photoredox arylations and their applications. 4.3. Oxy-Arylation of Alkynes for the Synthesis of Benzofuran 4.4.

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Section: C−s Bond Formationmentioning

confidence: 99%

Aryldiazonium Salts in Photoredox Catalysis – Recent Trends

et al. 2021

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“…Sulfonated isobenzofuran‐1(3 H )‐ones were further synthesized from a reaction of 2‐vinylbenzoic acids, aryldiazonium tetrafluoroborates, and sulfur dioxide surrogate of DABCO·(SO 2 ) 2 under photocatalysis in the presence of visible light (Scheme ) . The reaction pathway was similar to the above, as shown in Scheme .…”

Section: Photo‐assisted Single Electron Transfer (Set) After Insermentioning

confidence: 99%

Photoinduced Sulfonylation Reactions through the Insertion of Sulfur Dioxide

Xie

et al. 2019

Eur J Org Chem

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Recent advances in the photoinduced sulfonylation reactions through the insertion of sulfur dioxide are summarized. Among the approaches developed in the sulfonylation reactions, the insertion of sulfur dioxide via radical process can be accomplished with the assistance of photoredox catalysis in the presence of visible light or under ultraviolet irradiation, depending the substrates used in the reactions. Under ultraviolet irradiation, the conversion can be completed under metal‐ and additive‐free conditions. It is noteworthy that alkyl halides possessing eliminable β‐hydrogen atom are effective as alkyl radical precursors with the insertion of sulfur dioxide. Two parts, according to the photoinduced reaction pathways, are introduced: (a) photo‐initiated formation of radical with the subsequent capture of sulfur dioxide; (b) photo‐assisted single electron transfer (SET) after insertion of sulfur dioxide. During the transformation, an oxidative or reductive single electron transfer would occur under visible light photoredox catalysis.

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“…Notably, the gram-scale reaction worked well and gave the products in 80% yield. 23 Also in 2018, the Han group constructed chiral sulfonyl lactones using the same substrates. This multistep asymmetric radical reaction was carried out in the presence of Cu(MeCN) 4 PF 6 as catalyst using bis[(S)-4tert-butyl-4,5-dihydrooxazol-2-yl]methane as chiral ligand under argon atmosphere at room temperature, resulting in the corresponding sulfonyl lactones in up to 95% yield and 88% ee.…”

Section: Scheme 12 Cu-mediated Difunctionalization Unsaturated Carboxmentioning

confidence: 99%

Radical Strategy for the Transition-Metal-Catalyzed Synthesis of γ-Lactones: A Review

Wei

Li²,

Wu³

et al. 2020

Synthesis

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The γ-lactone skeleton is very important component of various natural products, biological molecules, food additives, and perfumes. As a result, much effort has been made towards such compounds. In this review, we summarize recent progress in transition-metal-catalyzed annulation reactions for the formation of γ-lactone derivatives through a radical pathway. Various reagents, such as anhydrides, Togni’s reagent, TMSN3, arenesulfonyl chlorides, arenediazonium salts, dibenzoyl peroxides, O-benzoylhydroxylamine, NFSI, and α-halocarboxylic compounds, used in radical cyclization reactions are described, and the mechanisms of these radical annulation reactions are also discussed.1 Introduction2 Annulations of Alkenes with Anhydrides3 Annulations of Unsaturated Carboxylic Acids with Nucleophiles4 Annulations of Alkenes with α-Halocarboxylic Compounds5 Conclusions and Outlook

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Generation of sulfonated isobenzofuran-1(3H)-ones under photocatalysis through the insertion of sulfur dioxide

Cited by 66 publications

References 60 publications

Aryldiazonium Salts in Photoredox Catalysis – Recent Trends

Aryldiazonium Salts in Photoredox Catalysis – Recent Trends

Photoinduced Sulfonylation Reactions through the Insertion of Sulfur Dioxide

Radical Strategy for the Transition-Metal-Catalyzed Synthesis of γ-Lactones: A Review

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