Construction of Sulfonyl Phthalides via Copper-Catalyzed Oxysulfonylation of 2-Vinylbenzoic Acids with Sodium Sulfinates

Xiong, Yan‐Shi; Zhang, Bin; Yang, Yu; Weng, Jiang; Lu, Gui

doi:10.1021/acs.joc.9b01646

Cited by 30 publications

(22 citation statements)

References 69 publications

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“…[261] Copper-catalyzed difunctionalization of 2-vinylbenzoic acids with sodium sulfinates using DTBP or oxygen as the oxidizing agent also gave sulfonylmethyl-substituted lactones. [262] Polysubstituted furans 485 were synthesized via the addition of sodium sulfinates 483 to cyclopropylidene-propenones 482, followed by I 2 -mediated 5-endo-trig cyclization of the resulting adduct 484 (Scheme 211). The process was also carried out in one-pot mode.…”

Section: Construction Of Five-membered Heterocyclesmentioning

confidence: 99%

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

et al. 2020

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Oxidative coupling methodology is widely applied for the formation of carbon-carbon and carbon-heteroatom bonds. This review focuses on methods for oxidative sulfonylation of multiple bonds involving sulfonyl hydrazides, sulfinic acids and their salts as sulfonylation reagents. Under oxidative conditions, they generate sulfonyl radicals, trapped by multiple carbon-carbon bonds resulting in a variety of SO 2-containing products: mainly, vinyl and alkynyl sulfones, hydroxy-, keto, and halo-substituted sulfones, sulfonylated derivatives of carbo-and heterocycles. This exhaustive review summarizes 321 references from 1996 to 2020 with the specialization of the studies of the last five years, and is divided into the chapters according to the classes of compounds being sulfonylated.

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Section: Construction Of Five-membered Heterocyclesmentioning

confidence: 99%

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

et al. 2020

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“…The copper-catalyzed difunctionalization of 2-vinylbenzoic acids with sodium sulfinates to construct substituted lactones was reported by Lu group. [15] In this transformation, DTBP or O 2 was used as oxidant to release sulfonyl radical from sodium sulfinate. This reaction exhibited excellent functional group tolerance, high atom economy and high efficiency.…”

Section: Sulfonylation/cyclization With Alkenesmentioning

confidence: 99%

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

et al. 2020

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Sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides as readily available and efficient sulfonylation reagents have been extensively explored in recent years. Sulfonyl radical can be generated from these sulfonyl reagents via different methods, then the sulfonyl radical could react with various substrates via different pathways to afford the corresponding products. In this review, we will summarize the progress in sulfonylation via radical reaction using sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides in recent three years. In terms of the different sulfonylation reagents, we classify these sulfonylation reactions into four types: 1.

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“…24 Sulfonated -lactones derivatives were also synthesized by Weng, Lu, and co-workers by the Cu-catalyzed oxysulfonylation of 2-vinylbenzoic acids with sodium sulfinates employing CuCl 2 as the catalyst and di-tert-butyl peroxide or O 2 as the terminal oxidant (Scheme 13). 25…”

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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Construction of Sulfonyl Phthalides via Copper-Catalyzed Oxysulfonylation of 2-Vinylbenzoic Acids with Sodium Sulfinates

Cited by 30 publications

References 69 publications

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

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

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