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

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6246 - 6276

Published: Jan. 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.

Language: Английский

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Visible light-promoted [3+2] cyclization reaction of vinyl azides with perfluoroalkyl-substituted-imidoyl sulfoxonium ylides

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(41), P. 5407 - 5410

Published: Jan. 1, 2024

A visible-light-induced [3+2] cyclization of vinyl azides with perfluoroalkyl-substituted imidoyl sulfoxonium ylides has been developed and provides a new efficient method for the construction 1-pyrrolines.

Language: 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, Journal Year: 2024, Volume and Issue: 89(15), P. 10736 - 10747

Published: July 18, 2024

A rhodium(III)-catalyzed aldehydic C(sp

Language: Английский

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Transition-Metal-Free Radical Approach for the Synthesis of Isothiocyanates by Pyridinium 1,4-Zwitterionic Thiolates as a Sulfur Source

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

Herein, we disclose a novel, mild, transition-metal-free approach to synthesizing diversely functionalized isothiocyanates from the corresponding isocyanide precursors, achieving high excellent yields (up 97%). The current method sheds light on reactivity of pyridinium 1,4-zwitterionic thiolates as an unprecedented sulfur source strikingly distinct their previously known in ionic annulation reactions, showcasing innovative organic synthesis.

Language: 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, Journal Year: 2025, Volume and Issue: unknown

Published: March 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.

Language: Английский

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Tandem Synthesis of Polysubstituted Pyrroles via Cu(I)-Catalyzed Cyclization of Ketene N,S-Acetals with β-Ketodinitriles

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

A new approach to multifunctionalized pyrroles has been explored by the tandem cyclization of α-oxoketene-N,S-acetals with β-ketodinitriles using Cu(MeCN)4BF4 and Ag2CO3 in toluene under reflux conditions. The reaction involves C–C/C–N bond creation, is assumed proceed via enamine formation, intramolecular cyclization, rearrangement. potential methodology also demonstrated for a gram-scale as well some useful organic transformations. offers practical pathway achieve polysubstituted broad substrate scope good functional group tolerance.

Language: Английский

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Base‐Mediated Cascade Reaction of CF3‐Imidoyl Sulfoxonium Ylides and Diimides for the Synthesis of Functionalized Amidines

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 7, 2024

Abstract A base‐mediated cascade reaction of CF 3 ‐imidoyl sulfoxonium ylides (TFISYs) and diimides has been developed for the preparation functionalized amidines. In transformation, a nucleophilic addition subsequent [2,3]‐sigmatropic rearrangement ylide occur to enable an intramolecular migration dimethyl sulfoxide (DMSO). The unexpected result protocol demonstrates chameleonic reactivity TFISYs.

Language: Английский

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Synthesis of N-Aryl-4-trifluoromethylthiazol-2-amines via Insertion/Annulation of Trifluoromethylimidoyl Sulfoxonium Ylides with Sodium Thiocyanate

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12255 - 12262

Published: Aug. 16, 2024

An efficient p-TsOH-mediated insertion of sodium thiocyanate into trifluoromethylimidoyl sulfoxonium ylides has been reported, affording annulated N-aryl-4-trifluoromethylthiazol-2-amines in 42–84% yields a one-pot manner. This protocol encompasses variety with serving as the source "S–C═N" moiety thiazole ring. The versatile transformations resulting pharmacologically important were also demonstrated.

Language: Английский

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Assembly of Thiazino[3,4‐a]isoquinoline and Thiazepino[5,4‐a]isoquinoline Frameworks from Isoquinolinium 1,4‐Zwitterionic Thiolates via [5 + 1] and [5 + 2] Cycloaddition Reactions

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 18, 2024

Abstract Two cycloaddition modes of isoquinolinium 1,4‐zwitterionic thiolates have been established. Upon choosing α ‐bromo ketones as the counterpart, a range isoquinoline‐fused thiazines can be attained with yields ranging from moderate to excellent through formal [5+1] reaction pathway, exhibiting remarkable substrate adaptability and resilience diverse functional groups. Additionally, library unprecedented thiazepino[5,4‐ ]isoquinolines, novel category seven‐membered heterocycles, has synthesized via [5+2] pathway utilizing acetylenedicarboxylate reactive component. Notably, this process stands out for its exceptional 100 % atomic utilization efficiency.

Language: Английский

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