Catalyst‐Free Regioselective Sulfenylation of Imidazoheterocycles with Sulfonyl Hydrazides in Water

Chowdhury, Soumyadeep Roy; Fadikar, Pulak; Hoque, Injamam Ul; Maity, Soumitra

doi:10.1002/ajoc.201700670

Cited by 21 publications

(6 citation statements)

References 78 publications

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“…Barman and Liu both investigated the sulfonylation of indoles derivatives. The Maity group described the sulfenylation of imidazoheterocycles in water under heating condition, without any additive. The Lei group described the radical sulfonylation of arenes employing the electrochemical condition.…”

Section: Sulfonyl Radiacls‐mediated Reactionsmentioning

confidence: 99%

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: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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“…These reactions are associated with the release of simpler by products i. e., H 2 and H 2 O. Attempts have been made to develop alternative sulfur surrogates such as S 8, [28] carbon disulfide (CS 2 ) , [29] potassium thiocyanate (KSCN), [30] dimethyl sulfoxide (DMSO), [31] sodium thiosulfate (NaS 2 O 3 ), [32] thiourea, [33] sulfonyl chlorides, thiols, Bunte salts, [55] sodium sulfinates, [56][57][58][59][60][61][62][63][64][65][66] N-(aryl/alkylsulfanyl)succinimides, [67] disulfides and sulfonyl hydrazides [68][69][70][71][72][73][74][75][76][77][78][79][80][81][82][83][84] as a sustainable sulfur source. The optimum usage of electrochemical and visible light in a metal-free approach is also important from green chemistry prespective.…”

Section: Deepak Tomar Is Working As An Assistant Professor Of Chemistry In Rk (Pg) Government College Shamli Uttar Pradesh He Has Two Yeamentioning

confidence: 99%

Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

et al. 2021

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Transition metal‐free sulfenylation of C−H bonds for C−S bond formation has recently emerged as sustainable protocols for the functionalisation of various molecules. Researchers have extensively developed such protocols for the construction of biologically relevant sulfur scaffolds. There has been a gradual shift from metal‐catalyzed to metal‐free C−S bond formation methodologies, because the latter offer environmentally benign and inherently safe access to novel synthetic routes in organic chemistry. The present review offers a dynamic discussion on recent advances in transition metal‐free C−S bond formation via C−H bond functionalization using different surrogate sulfenylating reagents. The review has comprehensively been devoted to radical and ionic mechanistic approaches. Some simple and eco‐friendly reagents for sulfenylation viz. tertbutyl hydrogen peroxide (TBHP), hydrogen peroxide (H2O2), iodine/potassium persulphate (I2/K2S2O8), inorganic bases, strong organic acids, iodine, I2/triphenyl phosphine (PPh3), N‐chlorosuccinamide (NCS), N‐bromosuccinamide (NBS), potassium iodate (KIO3), I2/bovine serum albumin (BSA), tetrabutyl ammonium iodide (TBAI)/HBr and graphene oxide along with their mechanistic approach has been detailed in this review. Moreover, modern methods for the C−S bond formation i. e., biocatalyst, electrochemical and visible light induced sulfenylation, and traditional sulfenylation methodologies have also been incorporated.

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“…It is noteworthy that no additional catalyst is required in this reaction, and this protocol provides a new choice for the synthesis of aromatic sulfides. In 2018, Maity and co-workers 79 also developed an environmentally friendly regioselective thiolation of imidazo heterocycles using sulfonyl hydrazides in water without any catalyst and additive.…”

Section: Alternative Reductantsmentioning

confidence: 99%

Synthesis of Thioethers from Sulfonyl Chlorides, Sodium Sulfinates, and Sulfonyl Hydrazides

Huang

Qiu

et al. 2019

Synthesis

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Sulfur-containing moieties, especially thioethers (sulfides), play pivotal roles in the functionalities of many natural products, pharmaceutical compounds, and organic materials. In this review, we summarize the recent synthetic protocols of thioethers using thiolating reagents, including sulfonyl chlorides, sodium sulfinates, and sulfonyl hydrazides, as the ideal starting materials. Representative mechanisms for different types of reaction are also discussed.1 Introduction2 Synthesis of Thioethers from Sulfonyl Chlorides3 Synthesis of Thioethers from Sodium Sulfinates4 Synthesis of Thioethers from Sulfonyl Hydrazides5 Conclusion

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Catalyst‐Free Regioselective Sulfenylation of Imidazoheterocycles with Sulfonyl Hydrazides in Water

Cited by 21 publications

References 78 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Transition Metal‐Free Sulfenylation of C−H Bonds for C−S Bond Formation in Recent Years: Mechanistic Approach and Promising Future

Synthesis of Thioethers from Sulfonyl Chlorides, Sodium Sulfinates, and Sulfonyl Hydrazides

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