Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles

Zhang, Yuzhen; Mo, Zu‐Yu; Wang, Hengshan; Wen, Xiaoan; Tang, Hai‐Tao; Pan, Ying‐Ming

doi:10.1039/c9gc01201j

Cited by 85 publications

(17 citation statements)

References 44 publications

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“…The subsequent C−S coupling of sulfony radicals in C3‐position yielded the bifunctionalized indoles. In 2019, Pan and co‐workers demonstrated the similar sulfonylation and hydrazination under an electrochemical condition (Scheme ).…”

Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 98%

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Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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Sulfonyl hydrazides are widely used as organic reagents. Advances in the past decade are summarized in the following categories by key intermediates: (1) [RO2S.]; (2) RO2SSR; (3) [ArS.]; (4) [RO2S−]; (5) RSO2‐[Metal] species; (6) Ar‐[Metal] species; (7) RSX; (8) RS‐DBU; (9) nucleophilic amino group; (10) sulfonyl hydrazides as diazene or sulfinic acid surrogate. Reactions with alkenes, alkynes, aldehydes, alcohols, thiophenol, Grignard reagents, among others, are discussed. We hope this review will promote future research in this area.

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Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 98%

“…Normally, copper‐oxidant systems were efficient. Besides, both photosynthesis and electrosynthesis were also well investigated in these years. The radical addition to unsaturated bonds, C−H activation and coupling were all effective, which will be fully discussed herein.…”

Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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“…It should be mentioned that the generation of the CF 2 H radical is different from the CF 3 radical. At the anode, the Mn III ‐CF 2 H species is generated by anodic oxidation of Mn II in the presence of Langlois reagent [6j, f, 7g, 17] . Subsequently, Mn‐assisted delivery of CF 2 H⋅ to the olefin moiety and went through the same path as the CF 3 radical to obtain the target product 3 (for details, see Figure S6 in the Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Electrochemical Tri‐ and Difluoromethylation‐Triggered Cyclization Accompanied by the Oxidative Cleavage of Indole Derivatives

Yuan

Cui

Zhang

et al. 2021

Chemistry A European J

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Considering their unique roles in organic synthesis, and pharmaceutical and agrochemical applications, the development of fluoroalkylation, cyclization, and indole oxidative cleavage are important topics. Herein, an unprecedented electrochemical tri‐ and difluoromethylation/cyclization/indole oxidative cleavage process occurring in an undivided cell is presented. The protocol employs a readily prepared Langlois reagent as the fluoroalkyl source, affording a series of tri‐ or difluoromethylated 2‐(2‐acetylphenyl)isoquinoline‐1,3‐diones in good yields with excellent stereoselectivity. It is worth noting that this new methodology merges the fluoroalkylation/cyclization of N‐substituted acrylamide alkenes with the oxidative cleavage of an indole C(2)=C(3) bond under external oxidant‐free conditions.

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“…In the presence of a substituent at the 3 d position of indole 354 , only diazene products were formed in 42–52% yields. A similar process of sulfonylation‐hydrazination of indoles with sulfonyl hydrazides was carried out with electric current as the oxidant [199] . Electrochemical sulfonylation of 2 H ‐indazoles was also reported [200] …”

Section: Sulfonylation Of Heterocyclesmentioning

confidence: 95%

“…A similar process of sulfonylation-hydrazination of indoles with sulfonyl hydrazides was carried out with electric current as the oxidant. [199] Electrochemical sulfonylation of 2H-indazoles was also reported. [200] The reaction of diaryl(1H-indol-2-yl)methanols 357 with sodium sulfinates 358 in the presence of AgNO 3 in EtOH at 80°C under an inert atmosphere provided disulfonylation products 359 in 41-85% yields (Scheme 157).…”

Section: Sulfonylation Of Five-membered Heterocyclesmentioning

confidence: 98%

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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Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles

Abstract: We have developed electrochemically enabled chemoselective sulfonylation and hydrazination of C2,C3-unsubstituted indoles with arylsulfonyl hydrazide.

Cited by 85 publications

References 44 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Electrochemical Tri‐ and Difluoromethylation‐Triggered Cyclization Accompanied by the Oxidative Cleavage of Indole Derivatives

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

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