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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Self‐ or Acridinium‐Catalyzed Electrophotosynthesis of Thiocyanato Heterocycles from Activated Alkenes

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2352 - 2362

Published: April 5, 2024

Abstract While the emergence of electrophotochemistry provides opportunities, such a chemistry at this stage suffers from limited reaction types and high photocatalyst loadings. A self‐catalyzed electrophotosynthesis as well one with low loading is presented. These external‐oxidant‐free cyclizations are enabling applicable to range activated alkenes, affording diverse array thiocyanato heterocycles including 4‐pyrrolin‐2‐ones, isoquinoline‐1,3‐diones, indolo[2,1‐ ]isoquinolin‐6(5 H )‐ones, benzoimidazo[2,1‐ )‐ones indolin‐2‐ones, protocols amenable late‐stage diversification complex molecular architectures gram‐scale syntheses. Sunlight could serve light source, be conducted in an all‐solar‐driven mode using commercially available photovoltaic panel produce electricity.

Language: Английский

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

Organic Letters, Journal Year: 2024, Volume and Issue: 26(1), P. 62 - 67

Published: Jan. 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.

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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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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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, Journal Year: 2024, Volume and Issue: 13(5)

Published: Feb. 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.

Language: Английский

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Base-mediated formal [4+1] annulation of ortho-hydroxyphenyl substituted para-quinone methides and CF3-imidoyl sulfoxonium ylides to access trifluoroacetimidoyl-substituted 2,3-dihydrobenzofurans

Journal of Fluorine Chemistry, Journal Year: 2024, Volume and Issue: 277, P. 110308 - 110308

Published: June 7, 2024

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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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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Construction of trifluoromethyl-substituted enaminones via rhodium(III)-catalyzed aldehydic C(sp2)–H bond activation of N-sulfonyl-2-aminobenzaldehydes with CF3-imidoyl sulfoxonium ylides

Tetrahedron, Journal Year: 2024, Volume and Issue: unknown, P. 134408 - 134408

Published: Dec. 1, 2024

Language: Английский

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