Desulfitative Thioalkylation of Alkenes

Cao, Lidong; Jimeno, Ciril; Renaud, Philippe

doi:10.1002/adsc.202000657

Cited by 6 publications

(4 citation statements)

References 32 publications

(31 reference statements)

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“…Since working with gaseous trifluoromethyl iodide is tedious and costly, we looked for an alternative procedure based on the use of a commercially available, affordable, and easy to handle reagent. Recently, we reported that desulfitative processes are particularly efficient to run chloro‐ and thio‐ and azidoalkylation of alkenes [47–49] . Trifluoromethanesulfonyl chloride is a very common and commercially available reagent.…”

Section: Resultsmentioning

confidence: 99%

“…Recently, we reported that desulfitative processes are particularly efficient to run chloro-and thio-and azidoalkylation of alkenes. [47][48][49] Trifluoromethanesulfonyl chloride is a very common and commercially available reagent. Its use for the chlorotrifluoromethylation of alkenes [50] was pioneered by Kamigata et al using metal catalysis, [51][52][53][54] a reaction that could also be run under photoredox conditions, [55][56][57][58][59][60][61] as well as under classical radical initiation.…”

Section: Hydrotrifluoromethylation With Trifluoromethyl Iodide and Tr...mentioning

confidence: 99%

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Radical‐Mediated Hydroperfluoroalkylation of Unactivated Alkenes

et al. 2023

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The direct hydroperfluoroalkylation of a wide range of unactivated alkenes has been achieved at room temperature with readily available iodoperfluoroalkanes using 4‐tert‐butylcatechol as a source of hydrogen atom and triethylborane. The hydrotrifluoromethylation could also be achieved under these conditions using gaseous trifluoromethyl iodide. An experimentally simple two‐step, one‐pot hydrotrifluoromethylation process using the easy‐to‐use trifluoromethanesulfonyl chloride as the source of trifluoromethyl radicals has also been developed. Using these two approaches, a broad range of substrates, including isoprenoid natural products, were efficiently derivatized.

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Section: Resultsmentioning

confidence: 99%

Section: Hydrotrifluoromethylation With Trifluoromethyl Iodide and Tr...mentioning

confidence: 99%

Radical‐Mediated Hydroperfluoroalkylation of Unactivated Alkenes

et al. 2023

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“…Recently, we reported that desulfitative processes are particularly efficient to run chloro-and thio-and azidoalkylation of alkenes. [43][44][45][46] Trifluoromethanesulfonyl chloride is a very common and commercially available reagent. Its use for the chlorotrifluoromethylation of alkenes [47] was pioneered by Kamigata et al using metal catalysis, [48][49][50][51] a reaction that could also be run under photoredox conditions [52][53][54][55][56][57][58] as well as under classical radical initiation.…”

Section: Hydrotrifluoromethylation With Trifluoromethyl Iodide and Tr...mentioning

confidence: 99%

Radical Mediated Hydroperfluoroalkylation of Unactivated Alkenes

Sissengaliyeva

Dénès

Girbu

et al. 2023

Preprint

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The direct hydroperfluoroalkylation of a wide range of unactivated alkenes have been achieved at room temperature with readily available iodoperfluoroalkanes using 4-tert-butylcatechol as a source of hydrogen atom and triethylborane. The hydrotrifluoromethylation could also be achieved under these conditions using gaseous trifluoromethyl iodide. An experimentally simple two-step, one-pot hydrotrifluoromethylation process using the easy-to-use trifluoromethanesulfonyl chloride as the source of trifluoromethyl radicals has also been developed. Using these two approaches, a broad range of substrates, including isoprenoid natural products, were efficiently derivatized.

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“…烯烃也是一种重要的化工原料 [74] , 可与硫代磺酸酯反应, 经历不同的反应历程而合成具有特定官能团的分子, 如硫醚 [75] . Renaud 课题组 [76] 报道了一种硫代磺酸酯和烯烃发生的硫醚化反应(Eq. 13).…”

Section: 与烯类的加成反应应用unclassified

Research Progress in Synthesis and Application of Thiosulfonates

Yu¹,

Chen²,

Chen³

et al. 2022

Chinese Journal of Organic Chemistry

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As an important kind of synthons, thiosulfonates can react with alkynes, alkenes, aldehydes, and halogenated hydrocarbons to synthesize thioethers and sulfones. At the same time, some thiosulfonate compounds have anti-viral and anti-fungal bioactivities. The synthesis of thiosulfonates and their applications in organic synthesis have been under the spotlight. Thus, according to different types of catalysts and new progress in green chemistry, the synthesis progress of thiosulfonates is summarized. On the other hand, according to the types of reactants and reaction types, the application progress of thiosulfonates in organic synthesis is reviewed. In the future, among the researches on the construction of new sulfides with thiosulfonates, various difunctionalization reactions are still promising directions. Keywords thiosulfonate; green chemistry; C-S bond formation; photocatalysis; radical reaction; difunctionalization reaction 含硫有机化合物广泛出现在天然产物 [1] 、合成药物 [2] 、荧光探针 [3] 等分子中, 在诸多领域都有着十分广泛的应用 [4] . 硫代磺酸酯是一种特殊的硫化物, 它包含一个氧化态为 II 的硫原子和另一个氧化态为 VI 的硫原子, 这使它们能够与亲核试剂和亲电试剂反应 [5] . 硫代磺酸酯不仅可作为有机合成的合成子或者中间体 [6] , 而且具有良好的生物活性, 如抗病毒、抗真菌、抗寄生虫等作用 [7] . 因此, 硫代磺酸酯的制备与其在有机合成方法学中的应用备受人们关注 [8][9] . 鉴于此, 本文以不同的催化剂与绿色化学新进展为依据, 总结了常见的硫代磺酸酯的合成策略; 同时, 以反应物种类及其反应类型为依据, 重点对近年来硫代磺酸酯在有机合成上的应用进行了文献综述.

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Desulfitative Thioalkylation of Alkenes

Cited by 6 publications

References 32 publications

Radical‐Mediated Hydroperfluoroalkylation of Unactivated Alkenes

Radical‐Mediated Hydroperfluoroalkylation of Unactivated Alkenes

Radical Mediated Hydroperfluoroalkylation of Unactivated Alkenes

Research Progress in Synthesis and Application of Thiosulfonates

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