Domino nucleophilic trifluoromethylations of alkyl perfluorodithioesters

Тимошенко, Вадим М.; Portella, Charles

doi:10.1016/j.jfluchem.2009.04.004

Cited by 17 publications

(8 citation statements)

References 13 publications

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“…For example catalyzed by TASF (tris(dimethylamino)sulfonium difluorotrimethyl siliconate), the reaction of benzenesulfonyl fluoride with 1 gives (trifluoromethylsulfonyl)benzene in excellent yield under mild conditions (eq 5). Utilizing this thiophilic nucleophilic reaction, , S -trifluoromethyl ketene dithioacetals (and analogues) are prepared by Portella and co-workers (eq 6). , This reaction has been successfully used for the transformation of nucleophilic trifluoromethylating species into electrophilic one, , such as the synthesis of N -protected trifluoromethyl-substituted sulfoximines (eq 7).…”

Section: Reactions With B- P- and S-based Electrophilesmentioning

confidence: 99%

Trifluoromethyltrimethylsilane: Nucleophilic Trifluoromethylation and Beyond

et al. 2014

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Section: Reactions With B- P- and S-based Electrophilesmentioning

confidence: 99%

Trifluoromethyltrimethylsilane: Nucleophilic Trifluoromethylation and Beyond

et al. 2014

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“…This reaction presents an alternative approach for the synthesis of 2,3-dicarbonylpyrrole derivatives. , In contrast with the construction of 88 , in the synthesis of 95 with N -methylprop-2-yn-1-amine as the amine component, the thiophilic nucleophilic reaction ,− for formation of thiiranium intermediate 98 , (also see Scheme ) should be critical for the formation of 95 via 1,2-acyl migration (Scheme ). …”

Section: Heteroannulation Reactions Via Ketene Ns-acetalsmentioning

confidence: 99%

Chemistry of Ketene N,S-Acetals: An Overview

et al. 2016

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Push-pull alkenes, which bear electron-donating and -accepting group(s) at both termini of a C═C double bond, respectively, are of interest not only for their unique electronic properties but also for their importance as versatile building blocks in organic synthesis. In the world of ketene acetals having the push-pull alkene skeleton, ketene N,S-acetal is most likely the biggest family according to the number and types of these compounds. The first ketene N,S-acetal compound was reported in 1956. As a cyclic ketene N,S-acetal compound, nithiazine, the first lead structure of neonicotinoid insecticides, was reported in 1978. The characteristics of ketene N,S-acetals, which have the structural feature of ketene S,S-acetals and enaminones, make them versatile and easy to use, especially in cyclization and multicomponent reactions for the synthesis of various heterocyclic systems and related natural products. There has been an increasing wealth of information about the synthesis and synthetic applications of ketene N,S-acetals, especially, in recent years. This review provides comprehensive knowledge on the chemistry of ketene N,S-acetals.

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“…Ketene dithioacetals are useful intermediates in organic synthesis and have been used for the synthesis of heterocyclic compounds (Kolb, 1990;Ila et al, 2001). The synthesis of trifluoromethyl ketene dithioacetals plays an important role in the field of pharmaceuticals and agrochemicals (Gouault-Bironneau et al, 2012;Timoshenko & Portella, 2009). They have also been used to develop domino reactions owing to their ability to produce a wide range of substances of structural diversity and varied biological activities (Pan et al, 2013;Samai et al, 2012).…”

Section: Structure Descriptionmentioning

confidence: 99%