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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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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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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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 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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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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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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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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Synthesis of 1,4-oxathiins via [3+3] annulation of pyridinium 1,4-zwitterionic thiolates with iodonium ylides

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: July 1, 2024

A straightforward and valuable approach for the synthesis of 1,4-oxathiins has been developed via [3 ​+ ​3] annulation pyridinium 1,4-zwitterionic thiolates with iodonium ylides. C–S C–O bonds were formed in one pot manner this transformation, which features readily available substrates, excellent tolerance functional groups mild reaction conditions. It would be great value construction biological pharmacological activity.

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

Published: Jan. 1, 2024

Language: Английский

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