Catalytic carbon–sulfur bond formation by amphoteric vanadyl triflate: exploring with thia-Michael addition, thioacetalization, and transthioacetalization reactions

Chen, Chien‐Tien; Lin, Yow‐Dzer; Liu, Chengyuan

doi:10.1016/j.tet.2009.10.012

Cited by 38 publications

(18 citation statements)

References 81 publications

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“…Typically, thia‐Michael reactions are promoted by certain bases, fluoride ion, functionalized clays, silica gel, lanthanum salts and Brønsted acids . Expensive metal catalysts based on copper, cadmium, ruthenium and vanadium have also been reported. Most of these approaches suffer from one or more drawbacks like long reaction time, requirement of high temperature, low to moderate yields, the use of stoichiometric amounts of catalysts, and the use of metal catalysts which are expensive and environmentally unsafe.…”

Section: Methodsmentioning

confidence: 99%

_L- Proline Nitrate: An Amino Acid Ionic Liquid for Green and Efficient Conjugate Addition of Thiols to Sulfonamide Chalcones

et al. 2017

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L‐Proline nitrate catalysed simple, mild and efficient protocol for the synthesis of thia‐Michael adducts of sulfonamide chalcones has been described. L‐Proline nitrate facilitates the electrophilic activation of sulfonamide enones with acetonitrile as optimum dielectric constant of the solvent increases nucleophilicity of thiophenol. The present protocol features benefits such as mild reaction conditions, operational simplicity and excellent yields.

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Section: Methodsmentioning

confidence: 99%

_L- Proline Nitrate: An Amino Acid Ionic Liquid for Green and Efficient Conjugate Addition of Thiols to Sulfonamide Chalcones

et al. 2017

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“…This gap was bridged by the Chen group, who demonstrated VO(OTf) 2 as an effective catalyst for ap lethora of thiols, including aliphatic, electron-withdrawing, electron-donating, andb iaryl systems (Scheme 8). [30] Their optimized reactionc onditions involved the presenceo f5mol% VO(OTf) 2 at room temperature in am ixed MeCN/CH 2 Cl 2 (1:4)s olvents ystem. To determine the scope of this reaction, aw ide range of thiols, including aliphatic, aromatic, heteroaromatic, and several a,b-unsaturated carbonyl systems( both acyclic and cyclic systems), were investigated and found to be well-tolerated.…”

Section: Acid-catalyzed Thia-michaela Ddition Reactionsmentioning

confidence: 99%

Thia‐Michael Addition: An Emerging Strategy in Organic Synthesis

2018

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The thia-Michael addition reactionh as been demonstrated to be ah ighly powerful tool in organic synthesis. Indeed, the influential natureo ft his reactionh as been wellestablished in the fields of medicinal chemistry,c atalysis, drug discovery,a nd materials science. The emergence of numerous synthetic strategies that take advantage of thia-Michael addition reactions of electron-deficienta lkenes has unleashed countless opportunities for the design and synthesis of diverse biologically relevant organosulfurc ompounds. However,d espite myriad potential synthetic applications, there has not been anye xclusive reviewso ft he thia-Michael addition reaction. Therefore, this Focus Review plots the journeyo ft he thia-Michael addition reaction in organic synthesis, and is categorized according to catalyzed and catalyst-free thia-Michael addition reactions. Figure 1. Summary of the applicationsoft hia-Michael adducts.[a] Dr.Scheme1.Catalyzed pathways for the thia-Michael addition reaction.EW-G = electron-withdrawing group.Scheme2.Acetic-acid-catalyzed thia-Michael additionr eaction proposed by Allen et al. [24] AsianJ.O rg.Scheme3.Indium-bromide-catalyzed thia-Michael addition reaction.Scheme4.Thia-Michael addition reaction followed by a1 ,2-addition of TMSCN in one pot. TMSCN = trimethylsilyl cyanide.Scheme5.Bi III -catalyzedt hia-Michael additionreactiono fa,b-unsaturated carbonyl compounds. Tf = trifluoromethanesulfonyl.Scheme6.Bismuth-triflate-catalyzed synthesis of bis-thioether compounds. Bn = benzyl.Scheme7.Iron-/copper-catalyzed thia-Michael additionr eaction.Scheme8.VO(OTf) 2 -mediated synthesis of b-mercapto ketones. Np = naphthyl.Scheme9.Substrate scope for the synthesis of 3-sulfanyl-substituted 1-(arylamino)-pyrrolidine-2,5-diones.Scheme10. Regio-and enantioselective addition at the d position of conjugated systems.Scheme11. Mechanistic modelf or the enantioselective d addition of at hiol to an a,b,g,d-unsaturated dienone,catalyzed by achiral Fe III Àsalenc omplex.Scheme12. Chemoselectivesynthesis of 2-amino-3,1-benzothiazines (15) and 3,4-dihydroquinazoline-2-thiones (16)byu sing ortho-aminocinnamate (13)a nd isothiocyanates 14.Scheme13. Reactionmechanism for the chemoselective synthesis of 2amino-3,1-benzothiazines (15)and 3,4-dihydroquinazoline-2-thiones (16).Scheme14. ZrCl 4 -assisted three-component reactionf or the synthesiso fbaryl-b-mercapto ketones.Scheme15. LiF-nanocube-mediated thia-Michael addition reaction.Scheme57. Ni II -catalyzed enantioselective synthesiso f2-aryl-3-nitrothiochroman-4-ols.Scheme58. Te ntative reaction mechanism for the Ni II -catalyzed asymmetric synthesis of 2-aryl-3-nitrothiochroman-4-ols.Scheme59. Pepsin-catalyzed synthesis of functionalized chiral dihydrothiophenes.Scheme69. Mechanistic aspects of the stereoselectives ynthesis of tetrahydrothioxanthenones.Scheme70. Enantioselectivesynthesis of methyl 2-((R)-2-nitro-1-(aryl/heteroaryl)ethylthio)acetatesa nd thiomorpholin-3-ones.Scheme71. Water-accelerated thia-Michael additionr eaction proposedb y Chakraborti and co-work...

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“…Among them, these organosulfur compounds have been particularly prepared via thioacetalization of aldehydes though different synthetic methodologies, for instance, using resin‐bounded reagents, solid supported‐linker, in the presence of protic or Lewis acids . However, the vast majority of methodologies reported have used different metals as catalysts, including copper, hafnium, indium, ruthenium, vanadium . More recently, dithioacetals have also been effectively prepared via photo‐catalyzed transformations .…”

Section: Introductionmentioning

confidence: 99%

Sulfamic Acid‐Catalyzed Thioacetalization of Aldehydes under Solvent and Metal‐Free Conditions

et al. 2020

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Herein, we have reported a straightforward methodology for the synthesis of dithioacetals through a metal‐free catalyzed reaction of aldehydes with thiols. In this regard, sulfamic acid proved to be a very efficient catalyst for the preparation of desired products under conventional heating as well as ultrasound irradiation. Generally, the desired products were obtained with reasonable yields through a thioacetalization process, under mild reaction conditions. Noteworthy, sulfamic acid could be recovered from the reaction by simple filtration and it was reused in further reactions and it showed good catalytic activity until the third cycle. In addition, a series of control experiments have also been performed and a plausible reaction mechanism has been illustrated.

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Catalytic carbon–sulfur bond formation by amphoteric vanadyl triflate: exploring with thia-Michael addition, thioacetalization, and transthioacetalization reactions

Cited by 38 publications

References 81 publications

_L- Proline Nitrate: An Amino Acid Ionic Liquid for Green and Efficient Conjugate Addition of Thiols to Sulfonamide Chalcones

_L- Proline Nitrate: An Amino Acid Ionic Liquid for Green and Efficient Conjugate Addition of Thiols to Sulfonamide Chalcones

Thia‐Michael Addition: An Emerging Strategy in Organic Synthesis

Sulfamic Acid‐Catalyzed Thioacetalization of Aldehydes under Solvent and Metal‐Free Conditions

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