Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds via trifluoromethyl building blocks

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(31), С. 6246 - 6276

Опубликована: Янв. 1, 2024

Recent advances in the preparation of trifluoromethyl-containing heterocyclics via trifluoromethyl building block strategies over period from 2019 to present are systematically summarized and discussed.

Язык: Английский

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Rh(iii)-catalyzed C–H activation/annulation of N-carbamoylindoles with CF₃-imidoyl sulfoxonium ylides for the divergent synthesis of trifluoromethyl-substituted (dihydro)pyrimidoindolones

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(15), С. 3843 - 3848

Опубликована: Янв. 1, 2023

We have developed a Rh( iii )-catalyzed C–H activation/chemodivergent annulation of N -carbamoylindoles with TFISYs, allowing facile access to variety trifluoromethyl-substituted (dihydro)pyrimidoindolones high efficiency. Solvents play critical role in the selectivity reaction.

Язык: Английский

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Synthesis of CF₃–Isoquinolinones and Imidazole-Fused CF₃–Isoquinolinones Based on C–H Activation-Initiated Cascade Reactions of 2-Aryloxazolines

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10180 - 10196

Опубликована: Июль 4, 2024

Presented herein are novel syntheses of CF

Язык: Английский

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Synthesis of 5‐Trifluoromethylpyrroles from Heating‐Induced Annulation of Pyridinium 1,4‐Zwitterionic Thiolates with CF₃‐Imidoyl Sulfoxonium Ylides

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(19), С. 3382 - 3386

Опубликована: Авг. 16, 2023

Abstract A heating‐induced desulfuration annulation of pyridinium 1,4‐zwitterionic thiolates and CF 3 ‐substituted imidoyl sulfoxonium ylides has been achieved, allowing a route to biologically important 5‐trifluoromethylpyrroles. The transformation proceeds through an unusual ((3+3)‐1) pathway under metal‐free conditions with the extrusion 4‐methoxypyridine, sulfur DMSO. scale‐up reaction further obtained pyrrole products have performed demonstrate synthetic utility developed method.

Язык: Английский

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Copper-Mediated Cyclization of Terminal Alkynes with CF₃-Imidoyl Sulfoxonium Ylides To Construct 5-Trifluoromethylpyrroles

Organic Letters, Год журнала: 2024, Номер 26(11), С. 2249 - 2254

Опубликована: Март 7, 2024

A copper-mediated [3 + 2] cyclization of CF3-imidoyl sulfoxonium ylides and terminal alkynes has been demonstrated. This work provides a practical approach for assembling 5-trifluoromethylpyrroles with the merits broad substrate scope, good functional tolerance, mild reaction conditions. Control experiments DFT studies indicate that this may involve addition π-bonds by copper-carbene radicals hydrogen migration.

Язык: Английский

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Rhodium(III)-Catalyzed Coupling of Quinolin-8-carboxaldehydes with CF₃–Imidoyl Sulfoxonium Ylides by Chelation-Assisted C(sp²)-H Bond Activation for the Synthesis of Trifluoromethyl-Substituted Enaminones

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 10736 - 10747

Опубликована: Июль 18, 2024

A rhodium(III)-catalyzed aldehydic C(sp

Язык: Английский

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Synthesis of 2‐Trifluoromethyl‐4‐aminoquinolines via Heating‐Promoted Multi‐component Reaction of CF₃‐Imidoyl Sulfoxonium Ylides and Amines with Difluorocarbene as a C1 Synthon^†

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(23), С. 3205 - 3210

Опубликована: Июль 17, 2023

Comprehensive Summary A thermally‐induced multi‐component reaction of CF 3 ‐substituted imidoyl sulfoxonium ylides (TFISYs), amines and (triphenylphosphonio)difluoroacetate (PDFA) has been developed, allowing a facile access to 2‐trifluoromethyl‐4‐aminoquinolines in high yields. The proceeds smoothly with or without the addition sulfur utilizes difluorocarbene as C1 synthon under simply heating conditions. Mechanistic study reveals that in‐situ generated thiocarbonyl fluoride, isothiocyanate gem ‐difluoroalkene might act key intermediates.

Язык: Английский

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Divergent Synthesis of Trifluoromethyl-Substituted 1,2-Dihydroquinoxalines and Diimines by Cascade Reactions of CF₃–Imidoyl Sulfoxonium Ylides with Azo Compounds

Organic Letters, Год журнала: 2023, Номер 25(38), С. 7046 - 7050

Опубликована: Сен. 18, 2023

A base-mediated cascade reaction of CF3-imidoyl sulfoxonium ylides and azo compounds has been achieved, allowing for facile access to trifluoromethyl-substituted 1,2-dihydroquinoxalines diimines in moderate excellent yields. Noteworthy is that the unusual N-N bond cleavage rearrangement are involved transformations.

Язык: Английский

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Rh(III)-catalyzed C–H/C–C activation of benzoylacetonitriles and cyclization with CF3-imidoyl sulfoxonium ylides to 3-trifluoromethyl-isoquinolones

Journal of Catalysis, Год журнала: 2023, Номер 427, С. 115098 - 115098

Опубликована: Авг. 19, 2023

Язык: Английский

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Synthesis of Trifluoromethyl‐Containing 2,3‐Dihydrobenzofurans via a Formal [4+1] Annulation of In‐situ Generated o‐Quinone Methides and CF₃−Imidoyl Sulfoxonium Ylides

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(5)

Опубликована: Фев. 29, 2024

Abstract A metal‐free [4+1] annulation of in‐situ generated ortho ‐quinone methides ( o ‐QMs) and CF 3 −imidoyl sulfoxonium ylides (TFISYs) has been achieved under mild conditions, which provides a facile straightforward access to variety trifluoromethyl‐containing 2,3‐dihydrobenzofurans in moderate excellent yields.

Язык: Английский

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