Copper catalyzed direct tert-butyl sulfonylation of alkynes with t-butylsulfinamide leading to (E)-vinyl sulfones

Liu, Zhidong; Chen, Xiaolan; Chen, Jianyu; Qu, Lingbo; Xia, Yingya; Wu, Haitao; Ma, Huili; Zhu, Shaohua; Zhao, Yufen

doi:10.1039/c5ra13474a

Cited by 13 publications

(9 citation statements)

References 33 publications

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“…Qu, Chen and co-workers developed a copper-catalyzed sulfonylation of alkynes with tert-butylsulfinamide (Scheme 51). 90 Phosphorous acid serves as terminal reducing agent and the oxidation of the sulfinyl (SO) to the sulfonyl (SO 2 ) moiety takes place under the reaction conditions.…”

Section: Scheme 50mentioning

confidence: 99%

Recent Advances in the Synthesis of Sulfones

2016

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Sulfones are versatile intermediates in organic synthesis and important building blocks in the construction of biological active molecules or functional materials. This review provides a summary of recent developments in the synthesis of sulfones. 1 Introduction 2 Classical Methods and Variants 2.1 Oxidation of Sulfides 2.2 Aromatic Sulfonylation 2.3 Alkylation/Arylation of Sulfinates 2.4 Addition to Alkenes and Alkynes 2.5 Miscellaneous Methods 3 Metal-Catalyzed Coupling Reactions 4 Sulfone Synthesis by C-H Functionalization 5 Sulfur Dioxide Based Three-Component Approaches 6 Biological Synthesis of Sulfones 7 Conclusion

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Section: Scheme 50mentioning

confidence: 99%

Recent Advances in the Synthesis of Sulfones

2016

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“…44 Loh's group 45 described the alternative Cu(I)-catalyzed methyl sulfonylation of alkynes using DMSO as a methyl sulfone source. In 2015, Zhao and co-workers 46 reported a study on the copper-catalyzed tert-butyl sulfonylation reaction of alkynes with tert-butanesulfinamide for the construction of (E)vinyl sulfones. Tert-butanesulfinamide react with alkynes in DMF in the presence of CuSO4• 5H2O, TFA and H3PO3 to afford the corresponding products in 51-79% yields.…”

Section: Reaction With Alkynesmentioning

confidence: 99%

“…Zhao and co-workers have proposed a very complicated mechanism for this reaction (Scheme 21). 46 But we think that this reaction involved acid hydrolysis of tert-butanesulfinamide into tert-butanesulfinic acid by H3PO3 and then electrophilic addition of tert-butanesulfinic acid to phenylacetylenes to provide 2arylvinyl sulfones.…”

Section: Reaction With Alkynesmentioning

confidence: 99%

“…44 In 2014, Loh and Jiang 45 described an alternative Cu(I)-catalyzed methyl sulfonylation of alkynes using DMSO as a methyl sulfone source. In 2015, Chen, Qu, and co-workers 46 reported a copper-catalyzed tert-butyl sulfonylation reaction of alkynes. tert-Butanesulfinamide reacts with alkynes in DMF in the presence of CuSO 4 •5H 2 O as the catalyst, TFA and H 3 PO 3 , and DMF as the solvent to afford various tertbutyl (E)-vinyl sulfones in 51-79% yields (Scheme 20).…”

Section: Short Review Synthesis 32 Reaction With Alkynesmentioning

confidence: 99%

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Syntheses and Transformations of Sulfinamides

Zhang¹,

Xi²,

He³

et al. 2021

Synthesis

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Sulfinamides, especially enantiopure sulfinamides, are widely used in organic and medicinal synthesis. Syntheses and transformations of racemic and enantioenriched sulfinamides have achieved great progress. Especially sulfinamides demonstrate interesting and valuable reactivity, which deserves to be concerned. This review summarizes the latest development in the synthesis and transformation of sulfinamides and will be helpful for future related research.

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“…In 2015, Chen and Zhao'group 36 disclosed that (E)-vinyl sulfone scaffolds could be obtained from t-butylsulfinamide and alkynes in the CuSO 4 -phosphorous acid catalytic system (Scheme 18). It is the first example of the use of t-butylsulfinamide as a sulfur source to prepare vinyl sulfones.…”

Section: Scheme 18 Synthesis Of (E)-vinyl Sulfones From Alkynes and Tmentioning

confidence: 99%

Recent advances in the synthesis of vinyl sulfones

2016

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Development of methodology for the preparation of vinyl sulfones is of significant interest to organic chemists. Recently, numerous useful methods have been developed, mainly including direct sulfonylation of olefins and alkynes, decarboxylative sulfonylation of α,β-unsaturated carboxylic acids and decomposition of tosylhydrazones. This review will focus on recent achievements in vinyl sulfones synthesis and the mechanisms of the reactions are also discussed.

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Copper catalyzed direct tert-butyl sulfonylation of alkynes with t-butylsulfinamide leading to (E)-vinyl sulfones

Abstract: The first copper-catalyzed tert-butyl sulfonylation reaction of alkynes with t-butylsulfinamide for the construction of (E)-vinyl sulfones has been developed.

Cited by 13 publications

References 33 publications

Recent Advances in the Synthesis of Sulfones

Recent Advances in the Synthesis of Sulfones

Syntheses and Transformations of Sulfinamides

Recent advances in the synthesis of vinyl sulfones

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