Exploring the Reactivity of Trifluoromethyl Tolueneselenosulfonate with Alkynes under Copper Catalysis

Ghiazza, Clément; Debrauwer, Vincent; Billard, Thierry; Tlili, Anis

doi:10.1002/chem.201705231

Cited by 44 publications

(12 citation statements)

References 46 publications

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“…Later, they reported the copper‐catalyzed trifluoromethylselenolation of terminal alkynes (Scheme 31). [55] The yields of arenes with electron‐donating groups were good ( 44 a – 44 b ), while the yields of arenes with electron‐withdrawing groups were only moderate ( 44 c – 44 d ). For the substrates bearing an amine, ether, ester, as well as amide, the products were obtained in moderate to good yields ( 44 e – 44 h ).…”

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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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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“…[55] In 2018, Billard and Tlili proposed to study the reactivity of TsSeR F reagents with terminal alkynes under copper catalysis (Scheme 20C and Scheme 20D). [56] Indeed, the direct fluoroalkylselenolation was achieved under mild conditions affording the desired products 55 in low to good yields for both aromatic and aliphatic starting materials. Once again, the formation of an organocopper (I) species, namely alkynyl copper (I), is invoked to activate the fluoroalkylselenylated source.…”

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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“…[55] In 2018, Billard & Tlili proposed to study the reactivity of TsSeRF reagents with terminal alkynes under copper catalysis (Scheme 20, C & D). [56] Indeed, the direct fluoroalkylselenolation was achieved under mild conditions affording the desired products 55 in low to good yields for both aromatic and aliphatic starting materials. Once again, the formation of an organocopper (I) species, namely alkynyl copper (I), is invoked to activate the fluoroalkylselenylated source.…”

Section: Se-(fluoroalkyl) Arylselenosulfonatesmentioning

confidence: 99%

Front Cover: Synthesis, Reactivity and Activation Modes of Fluoroalkyl Thiosulfonates and Selenosulfonates (Eur. J. Org. Chem. 41/2021)

Ghiazza

Billard

2021

Eur J Org Chem

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The Front Cover shows highly versatile reagents gravitating in the galaxy of reactions aiming to introduce fluorine‐containing units, namely fluoroalkylchalcogenosulfonates. Indeed, this family of compounds enables trifluoromethylation, trifluoromethylsulfonylation, fluoroalkylthiolation, and fluoroalkylselenolation reactions through several activation modes. Thus, these valuable fluorinated motifs can be introduced following electrophilic, nucleophilic, or radical pathways onto a plethora of organic substrates. More information can be found in the Minireview by C. Ghiazza and T. Billard.

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Exploring the Reactivity of Trifluoromethyl Tolueneselenosulfonate with Alkynes under Copper Catalysis

Cited by 44 publications

References 46 publications

Recent Advances in the Development of Direct Trifluoromethylselenolation Reagents and Methods

Recent Advances in the Development of Direct Trifluoromethylselenolation Reagents and Methods

Synthesis, Reactivity and Activation Modes of Fluoroalkyl Thiosulfonates and Selenosulfonates

Front Cover: Synthesis, Reactivity and Activation Modes of Fluoroalkyl Thiosulfonates and Selenosulfonates (Eur. J. Org. Chem. 41/2021)

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