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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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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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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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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Synthesis of Spiro 3,3′-Cyclopropyl Oxindoles via Cyclopropanation of 3-Alkenyl-oxindoles with CF₃-Imidoyl Sulfoxonium Ylides

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

Опубликована: Март 4, 2025

A catalyst and additive-free [2+1] annulation of 3-alkenyl-oxindoles with CF3-imidoyl sulfoxonium ylides (TFISYs) for the construction spiro 3,3'-cyclopropyl oxindoles has been achieved. cascade intermolecular Micheal-addition reaction intramolecular nucleophilic substitution sequence might be involved in transformation, which afforded a wide range multisubstituted oxindole products high efficiency diastereoselectivity.

Язык: Английский

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Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications

Chemical Reviews, Год журнала: 2025, Номер unknown

Опубликована: Апрель 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Язык: Английский

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Formal (4+2) cycloaddition of azoalkenes with trifluoromethylimidoyl sulfoxonium ylides: synthesis of trifluoromethyl pyridazine derivatives

Chemical Communications, Год журнала: 2023, Номер 59(83), С. 12495 - 12498

Опубликована: Янв. 1, 2023

CF3-substituted imidoyl sulfoxonium ylides (TFISYs) are extraordinarily versatile and powerful synthons for use in cyclization chemistry that affords diverse N-heterocycles. We first reacted TFISYs as a two-atom synthon with readily available azoalkenes then subjected the products to metal-free formal (4+2) cycloaddition chemistry. This protocol features mild conditions broad substrate scope, is simple operate, provides highly functionalized trifluoromethylpyridazines widely found bioactive molecules.

Язык: Английский

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Synthesis of Multifunctionalized Thiazolidine‐4‐thiones via [2+2+1] Annulation of Isothiocyanates and CF₃‐Imidoyl Sulfoxonium Ylides

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4672 - 4676

Опубликована: Ноя. 10, 2023

Abstract 2‐Iminothiazolidin‐4‐one, 5‐ethylidenethiazolidin‐4‐one, and thiazolidine‐4‐thione are all medicinally relevant structures. In this work, a NaSO 2 CF 3 ‐promoted [2+2+1] cascade annulation reaction of ‐imidoyl sulfoxonium ylides isothiocyanates was reported to synthesize variety decorated thiazolidine‐4‐thiones in 35–91% yields with exclusive stereoselectivity. The gram‐scale further chemoselective S ‐alkylations demonstrated the synthetic utilities transformation.

Язык: Английский

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