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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Chameleonic Reactivity of Imidoyl Sulfoxonium Ylides: Access to Functionalized Pyrroles and Dihydro-pyridines

Organic Letters, Год журнала: 2024, Номер 26(1), С. 62 - 67

Опубликована: Янв. 3, 2024

We have found a chameleonic reactivity of imidoyl sulfoxonium ylides. On the one hand, ylides react with electron-deficient reagents, such as alkynyl esters, to lead formation 1,2-dihydro-pyridines. The methyl group attached sulfur atom acts methylene donor. other pyridinium 1,4-zwitterionic thiolates, which leads functionalized pyrroles. Both transformations feature mild reaction conditions and good functional tolerance.

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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Construction of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides and derivatives

Chemical Communications, Год журнала: 2023, Номер 59(33), С. 4872 - 4890

Опубликована: Янв. 1, 2023

Recent advances in the direct synthesis of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides (TFAICs) and derivatives, including trifluoroacetimidohydrazides (TFAIHs) CF3-imidoyl sulfoxonium ylides (TFISYs), are systematically summarized discussed. The cascade annulation reactions synthons with suitable coupling partners have emerged as a powerful promising tool for construction variety trifluoromethyl-substituted heterocycles. Compared other building blocks, TFAICs derivatives notable merits easy availability handling, relative stability safety, high reactivity.

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 5‐Trifluoromethyl‐1,4‐dihydro‐1,2,4‐triazines via Base‐mediated [3+3] Cycloaddition of Nitrile Imines and CF₃‐Imidoyl Sulfoxonium Ylides

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(9), С. 1521 - 1525

Опубликована: Март 31, 2023

Abstract An approach for the construction of 5‐trifluoromethyl‐1,4‐dihydro‐1,2,4‐triazines has been developed via base‐mediated [3+3] cycloaddition in‐situ generated nitrile imines and CF 3 ‐substituted imidoyl sulfoxonium ylides. The metal‐free protocol is characterized by readily available starting materials, mild conditions, a broad substrate scope, high efficiency, good synthetic prospect, scalability. magnified image

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 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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Rh(III)‐Catalyzed Cascade Cyclization of 2‐Aryl‐3H‐indoles and CF₃‐Imidoyl Sulfoxonium Ylides Toward Trifluoroacetimidoyl‐Substituted 11H‐Isoindolo[2,1‐a]indoles

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(22), С. 3855 - 3860

Опубликована: Окт. 18, 2023

Abstract A rhodium(III)‐catalyzed C−H activation/[4+1] annulation of 2‐aryl‐3 H ‐indoles and CF 3 ‐substituted imidoyl sulfoxonium ylides (TFISYs) has been achieved, producing a wide variety trifluoroacetimidoyl‐substituted 11 ‐isoindolo[2,1‐a]indoles in 51–86% yields. The cascade reaction involves imidoylmethylation, tautomerization AgOAc‐mediated C−N bond formation sequence. could be scaled up to 2 mmol scale.

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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