Electrochemical Sulfonylation/Heteroarylation of Alkenes via Distal Heteroaryl <i>ipso</i>-Migration

Zheng, Ming‐Wei; Yuan, Xin; Cui, Yu‐Sheng; Qiu, Jiang‐Kai; Li, Guigen; Guo, Kai

doi:10.1021/acs.orglett.8b03191

Cited by 64 publications

(23 citation statements)

References 111 publications

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“…This ipso-aryl group migration process is similar to those presented in Schemes 14 and 23. Guo and coworker reported electrochemical sulfonylheteroarylation reacti kenes involving heteroaryl group migration (Scheme 27) [50]. The arylsulfonyl generated from sulfinic acid at the anode add to benzothiazole ring for heteroary tion followed by single-electron oxidation at the anode to afford cations and then p 47 after deprotonation.…”

Section: Scheme 26 Electrochemical Difunctionalization Of Styrenesmentioning

confidence: 99%

Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions

Yao

Zhang

2020

Molecules

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Popular and readily available alkenes and alkynes are good substrates for the preparation of functionalized molecules through radical and/or ionic addition reactions. Difunctionalization is a topic of current interest due to its high efficiency, substrate versatility, and operational simplicity. Presented in this article are radical addition followed by oxidation and nucleophilic addition reactions for difunctionalization of alkenes or alkynes. The difunctionalization could be accomplished through 1,2-addition (vicinal) and 1,n-addition (distal or remote) if H-atom or group-transfer is involved in the reaction process. A wide range of moieties, such as alkyl (R), perfluoroalkyl (Rf), aryl (Ar), hydroxy (OH), alkoxy (OR), acetatic (O2CR), halogenic (X), amino (NR2), azido (N3), cyano (CN), as well as sulfur- and phosphorous-containing groups can be incorporated through the difunctionalization reactions. Radicals generated from peroxides or single electron transfer (SET) agents, under photoredox or electrochemical reactions are employed for the reactions.

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Section: Scheme 26 Electrochemical Difunctionalization Of Styrenesmentioning

confidence: 99%

Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions

Yao

Zhang

2020

Molecules

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“…An efficient electrooxidative sulfonylation/heteroarylation of alkenes with sulfinic acids via distal heteroaryl ipso-migration was achieved by Guo group. [71] Various sulfonated heteroarenes can be prepared efficiently using this method. A radical pathway was proposed for this reaction.…”

Section: Sulfonylation 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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“…The reaction was carried out in an undivided electrochemical cell at room temperature using Bu 4 NBF 4 as the supporting electrolyte (Scheme 73). [92] Apparently, the process begins from the deprotonation of the starting sulfinic acid 157 with the formation of the corresponding sulfinate anion A , which is oxidized on anode into sulfonyl radical B . After that, radical B is trapped by tertiary allyl alcohol 156 generating C‐centered radical C , which rearranges into radical D with the migration of R 2 .…”

Section: Sulfonylation Of Unactivated Multiple Bondsmentioning

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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Electrochemical Sulfonylation/Heteroarylation of Alkenes via Distal Heteroaryl ipso-Migration

Cited by 64 publications

References 111 publications

Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions

Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions

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

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

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