Recyclable imidazolium ion-tagged nickel catalyst for microwave-assisted C–S cross-coupling in water using sulfonyl hydrazide as the sulfur source

Saini, Vaishali; Khungar, Bharti

doi:10.1039/c8nj00904j

Cited by 28 publications

(14 citation statements)

References 83 publications

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“…Oxidative addition of thiosulfonates to copper or nickel catalyst were able to form active metal species. The Tian group created a copper/byp‐catalyzed synthesis of thioethers with boronic acids (Eq.…”

Section: Formation and Application Of Thiosulfonatesmentioning

confidence: 99%

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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: Formation and Application Of Thiosulfonatesmentioning

confidence: 99%

“…Khungar and co‐workers devised a nickel‐catalyzed synthesis of thioethers by the C−S cross‐coupling of aryl sulfonyl hydrazides and alkyl halides (Eq. 45‐1).…”

Section: Formation and Application Of Thiosulfonatesmentioning

confidence: 99%

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

et al. 2020

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“…The incorporated imidazolium functionality supported the reusability of the catalyst; a marginal reduction of its activity was observed at the end of the fifth run, a yield of 86% was dropped to 80%. Although the principle of the reaction was innovative, the use of double amount of arylsulfonyl hydrazides increases the side products, which in turn could complicate the purification step [139] …”

Section: Formation Of Carbon‐chalcogen Bondmentioning

confidence: 99%

Modern Development in Copper‐ and Nickel‐Catalyzed Cross‐Coupling Reactions: Formation of Carbon‐Carbon and Carbon‐Heteroatom bonds under Microwave Irradiation Conditions

Salih

2022

Asian J Org Chem

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The use of transition metals in cross‐coupling reactions has been verified as a powerful tool in synthetic organic chemistry to access valuable pharmaceutical intermediates and functional organic molecules. Copper compounds were described for building a variety of Carbon‐Carbon and Carbon‐Heteroatom bonds more than a century ago. Whereas nickel‐catalyzed cross‐coupling was emerged in the 1972. The general reactivity of the reaction conversion was enhanced during the last two decades, particularly under microwave irradiation conditions. The focus of this review article accentuates the recent development and sustainable achievement of copper‐ and nickel‐catalyzed cross‐coupling of different electrophiles and nucleophiles or two sort of nucleophiles under microwave irradiation conditions. The published cross‐coupling protocols during the last ten years were critically reviewed, this includes the type and amount of metal catalyst used, solventless and ligandless conditions and the application in the synthesis of complex heterocycles. Furthermore, various proposed reaction mechanisms covering radical path or through the involvement of metal complexes in different oxidation states were highlighted and discussed.

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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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Recyclable imidazolium ion-tagged nickel catalyst for microwave-assisted C–S cross-coupling in water using sulfonyl hydrazide as the sulfur source

Abstract: Recyclable nickel(ii) catalyst promoted sulfenylation of aryl halides with sulfonyl hydrazides in water using microwave irradiation under mild conditions is reported.

Cited by 28 publications

References 83 publications

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

Modern Development in Copper‐ and Nickel‐Catalyzed Cross‐Coupling Reactions: Formation of Carbon‐Carbon and Carbon‐Heteroatom bonds under Microwave Irradiation Conditions

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

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