Visible light-promoted defluorinative alkylation/arylation of α-trifluoromethyl alkenes with thianthrenium salts

Green Chemistry, Год журнала: 2024, Номер 26(17), С. 9371 - 9377

Опубликована: Янв. 1, 2024

Defluorinative alkylation and arylation between thianthrenium salts α-trifluoromethyl alkene to afford gem -difluoroolefins by easily recycling thianthrene under visible light irradiation free of metal photocatalyst.

Язык: Английский

---

Visible Light Photoredox-Catalyzed Radical Defluorinative Arylation of α-Trifluoromethyl Alkenes with Aryl Chlorides

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 26, 2025

Photocatalytic defluorinative cross-coupling reactions of α-trifluoromethyl alkenes with diverse radical precursors have emerged as a powerful strategy for the synthesis gem-difluoroalkenes. However, arylation is relatively rare due to limitation aryl precursors. Aryl chlorides, ideal candidates, remain large challenge in this reaction because chemical inertness C(sp2)–Cl bond and their high negative reduction potential. Herein, we report chlorides through consecutive photoinduced electron transfer (ConPET) process. This protocol features mild conditions, operational simplicity, wide substrate scope, functional group tolerance, producing range benzylic gem-difluoroalkenes moderate good yields. The scale-up valuable transformations products demonstrate great potential applications approach.

Язык: Английский

---

Visible-Light-Mediated Addition Reactions of Sulfur-Containing Reagents with α-Trifluoromethyl Alkenes

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 22, 2025

Herein, we described the addition reactions of sulfur-containing reagents (sodium sulfinates, dithiosulfonates) with α-trifluoromethyl alkenes under visible light. A series trifluoromethyl sulfonates were synthesized via visible-light-induced radical reaction sodium sulfinates and to obtain protons from solvent. dithiosulfonated derivatives bifunctionalization dithiosulfonates.This strategy has advantages mild conditions, good substrate universality high yield up 99% yield.

Язык: Английский

---

Visible Light‐Mediated Defluorination to Access 1,1‐Difluoro‐1,3‐Enynes

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2246 - 2251

Опубликована: Март 29, 2024

Abstract Herein, a visible light‐mediated defluorination reaction to access 1,1‐difluoro‐1,3‐enynes is described. Compared with previous studies, this protocol employs more readily accessible acids as radical precursor under redox‐neutral conditions. Moreover, the exhibits high compatibility diverse primary, secondary and tertiary acids, especially natural amino drug‐derived acids. Preliminary mechanistic investigations reveal that pathway involved in catalytic cycle.

Язык: Английский

---

Synthesis of gem-Difluorohomoallyl Amines via a Transition-Metal-Free Defluorinative Alkylation of Benzyl Amines with Trifluoromethyl Alkenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8342 - 8356

Опубликована: Май 31, 2024

A mild and transition-metal-free defluorinative alkylation of benzyl amines with trifluoromethyl alkenes is reported. The features this protocol are easy-to-obtain starting materials, a wide range substrates, functional group tolerance as well high atom economy, thus offering strategy to access variety

Язык: Английский

---

Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes to construct densely functionalized α-CF₃ tertiary alcohols

Green Chemistry, Год журнала: 2024, Номер 26(15), С. 8694 - 8700

Опубликована: Янв. 1, 2024

Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes under an air atmosphere was developed to construct densely functionalized α-CF 3 tertiary alcohols.

Язык: Английский

---

Visible Light Induced Selective Cleavage of Single C(sp3)-F Bond in Trifluoromethyl Groups Containing Compounds

Tetrahedron, Год журнала: 2024, Номер 163, С. 134155 - 134155

Опубликована: Июль 16, 2024

Язык: Английский

---

Nickel-catalyzed directed hydrodefluorination by using water as a hydride source

Journal of Catalysis, Год журнала: 2024, Номер unknown, С. 115754 - 115754

Опубликована: Сен. 1, 2024

Язык: Английский

---

Photoredox-Catalyzed Markovnikov Hydroamination of Alkenes with Azoles

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Окт. 30, 2024

A visible-light induced intermolecular hydroamination of alkenes with azoles is reported, delivering pharmaceutically valuable N-benzyl in high yields excellent Markovnikov selectivity. Mechanistic studies suggest that the process initiated by energy transfer excited photocatalyst alkenes, followed single electron reduction, protonation, and subsequent oxidation to afford key alkyl carbocation intermediate. This protocol exhibits advantages broad functional group tolerance, atom economy, efficiency, mild reaction conditions.

Язык: Английский

---

Electrochemical Decarboxylative Trifluoromethylation of Cinnamic Acids Revisited: A Combined Experimental and Computational Study

Chemistry - An Asian Journal, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 11, 2024

β-(Trifluoromethyl)styrenes are potentially useful building blocks for the synthesis of organofluorine compounds because their electron-deficient C=C double bonds can undergo diverse transformations. One most practical methods preparing β-(trifluoromethyl)styrenes is decarboxylative trifluoromethylation readily available cinnamic acid derivatives using Langlois reagent as a less expensive trifluoromethyl source. We revisited electrochemical to identify modified conditions that reduce loading without additional additives. The reaction mechanism was computationally investigated gain insight into dependence product yields on aryl terminal groups. synthetic utility obtained demonstrated by transformation 4-aryl-3-(trifluoromethyl)pyrrolidines.

Язык: Английский

---