Ferric chloride-promoted direct trifluoromethylselenolation of nitrogen-containing heterocyclic compounds by Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate in water

Zhao, Xia; Wei, Xianfu; Tian, Miaomiao; Zheng, Xiancai; Ji, Liangshuo; Li, Quan; Lin, Yanhong; Lu, Kui

doi:10.1016/j.tetlet.2019.06.002

Cited by 31 publications

(28 citation statements)

References 53 publications

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“…Pleasingly, functional groups such as trifluoromethyl, silyl ether, and boronic esters as well as primary amide, unprotected aniline, free alcohol, and free carboxylic acid were tolerated affording moderate to good yields of 3 and high recovery of the corresponding additives. Noteworthy, the electrochemical protocol affords similar yields than the previously reported approaches that require stoichiometric quantities of reducing or activating agents [43–50] . Comparable limitations are also observed with non‐activated alkyl halides delivering low yields of the desired products.…”

Section: Resultsmentioning

confidence: 63%

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Electrochemical Trifluoromethylselenolation of Activated Alkyl Halides

et al. 2022

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A practical electrochemical method for the generation of CF3Se− anion from a shelf‐stable reagent (TsSeCF3) is reported allowing the metal‐free trifluoromethylselenolation of activated alkyl halides. Trifluoromethylselenolated compounds have been obtained in modest to excellent yields under the optimized reaction conditions. Finally, cyclic voltammetric and 19F NMR studies are presented and allowed to gain insight into the reaction mechanism.

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Section: Resultsmentioning

confidence: 63%

“…Noteworthy, the electrochemical protocol affords similar yields than the previously reported approaches that require stoichiometric quantities of reducing or activating agents. [43][44][45][46][47][48][49][50] Comparable limitations are also observed with non-activated alkyl halides delivering low yields of the desired products.…”

Section: Resultsmentioning

confidence: 99%

Electrochemical Trifluoromethylselenolation of Activated Alkyl Halides

et al. 2022

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“…Using TsSeCF 3 as an electrophilic trifluoromethylselenolation reagent, Zhao and co‐workers reported the FeCl 3 ‐promoted trifluoromethylselenolation of electron‐rich nitrogen‐containing heteroarenes, such as indoles (Scheme 31, 46 a – 46 h ), pyrrole( 46 i ), pyrazole ( 46 j ), indolizine ( 46 k ) and 1,3,5‐trimethoxybenzene ( 46 l )(Scheme 32). [56] The role of FeCl 3 was acted as a Lewis acid to activate TsSeCF 3 and increase its electrophilicity.…”

Section: Electrophilic Trifluoromethylselenolation Reagentsmentioning

confidence: 99%

Recent Advances in the Development of Direct Trifluoromethylselenolation Reagents and Methods

Wang

Zhang

et al. 2021

Adv Synth Catal

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The introduction of trifluoromethylchalcogen group (CF 3 O, CF 3 S and CF 3 Se) has attracted growing attention in the field of modern organofluorine chemistry. Compared with the CF 3 S and CF 3 O chemistry, methods for trifluoromethylselenolation are much less developed owing to the limited availability of CF 3 Se transfer reagents and synthetic methods. The CF 3 Se group introduces promising lipophilicity (Hansch-Leo parameter = 1.29) and strong electron-withdrawing effect (Hammett constants σ m = 0.44, σ p = 0.45) which are important parameters for the development of new pharmaceutically relevant compounds. Traditionally, the CF 3 Se compounds were synthesized by the nucleophilic trifluoromethylation of diselenides and selenocyanates, which suffered from harsh conditions and/or limited substrates scope. Compared with the indirect methods, the direct formation of CÀ SeCF 3 constitutes is a more efficient approach. In recent years, new reagents and methods were developed which enabled the incorporation of the trifluoromethylselenyl group directly under mild conditions, specifically in transition metal catalysis and photoredox catalysis. In this review, we will focus on direct trifluoromethylselenolation strategies based on the development of new trifluoromethylselenolation reagents and methods. 2.1. MÀ SeCF 3 (M=Hg, Cu, Ag) 2.2. [(bpy)CuSeCF 3 ] 2 2.3. (Me 4 N)SeCF 3 2.4. BTÀ SeCF 3 3. Electrophilic Trifluoromethylselenolation Reagents 3.1. In situ formed CF 3 SeCl from BnSeCF 3 + SO 2 Cl 2 3.2. TsSeCF 3 4. Miscellaneous 5. Conclusions

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“…In 2019, the group of Zhao applied the TsSeCF 3 reagent to trifluoromethylselenylate electron-rich aromatic compounds with a focus on nitrogen-containing heterocycles (Scheme 19C). [52] The reaction is performed in water at room temperature with FeCl 3 to activate and enhance the electrophilicity of the trifluoromethylselenyl group. Indoles were smoothly functionalized with good to excellent yields.…”

Section: So 2 -(Fluoroalkyl) Selenosulfonatesmentioning

confidence: 99%

Synthesis, Reactivity and Activation Modes of Fluoroalkyl Thiosulfonates and Selenosulfonates

Ghiazza

Billard

2021

Eur J Org Chem

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Reagent design is at the cornerstone of modern organofluorine chemistry. The past decades have seen the emergence of diverse families of reagents with the aim of introducing fluoroalkylthio or seleno groups in an efficient and selective way. Among them, highly versatile fluoroalkyl thiosulfonates and selenosulfonates are in the foreground of the recent developments. Their applicability is discussed in detail in this Minireview, with a specific focus on the reactivity and activation modes.

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Ferric chloride-promoted direct trifluoromethylselenolation of nitrogen-containing heterocyclic compounds by Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate in water

Cited by 31 publications

References 53 publications

Electrochemical Trifluoromethylselenolation of Activated Alkyl Halides

Electrochemical Trifluoromethylselenolation of Activated Alkyl Halides

Recent Advances in the Development of Direct Trifluoromethylselenolation Reagents and Methods

Synthesis, Reactivity and Activation Modes of Fluoroalkyl Thiosulfonates and Selenosulfonates

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