“On-water” defluorinative cyclization of trifluoromethyl enones with phosphine oxides: synthesis of polysubstituted furans

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 3974 - 3981

Published: Jan. 1, 2024

A defluorinative cyclization of readily available trifluoromethyl enones with phosphine oxides for the synthesis polysubstituted furans is developed in a pure water solution.

Language: Английский

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Perfluoroalkyl Editing of Fluoroalkynes: Chemo-, Regio-, and Stereoselective Synthesis of (E)-(2-Amino-fluoroalkenyl)pyrimidines

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 26, 2025

A chemo-, regio-, and stereoselective condensation reaction of perfluoroalkyl alkynes (PFAAs), (CH2O)n, (NH4)2CO3 through the cleavage five inert C(sp3)-F bonds at three distinct carbon sites, thereby establishing an unprecedented platform for synthesizing structurally unique (E)-(2-amino-fluoroalkenyl)pyrimidines, is first developed. Remarkably, this features mild conditions, good compatibility with various functional groups, excellent E-stereoselectivity, late-stage modification complex molecules, scalability, versatile synthetic transformations resulting heterocyclic compounds.

Language: Английский

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Combining (CH₂O)_n and (NH₄)₂CO₃ as a Formamidine Equivalent for “Four-in-One” Synthesis of Fluoroalkylated 2-H-Pyrimidines

Organic Letters, Journal Year: 2024, Volume and Issue: 26(33), P. 7078 - 7082

Published: Aug. 9, 2024

Multicomponent reactions hold the potential to maximize synthetic efficiency in preparation of diverse and complex molecular scaffolds. An unprecedented formal [3+1+1+1] annulation approach for one-step synthesis fluoroalkylated 2-H-pyrimidines commencing from perfluoroalkyl alkenes, paraformaldehyde, ammonium carbonate is described. By harnessing readily accessible (CH2O)n cheap (NH4)2CO3 as a formamidine surrogate, this method effectively replaces traditionally preformed amidines with pyrimidine assembly. The multicomponent reaction proceeds step-economical, operationally simple, metal-free, additive-free manner, featuring broad substrate scope, excellent functional group compatibility, scalability. elaboration obtained 2-H-pyrimidine further demonstrated alkylation vinylation its C2 position.

Language: Английский

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Modular Synthesis of Furans with Four Nonidentical Substituents by Aqueous Defluorinative Reaction of Trifluoromethyl Enones with Two Nucleophiles

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 24, 2024

A three-component reaction of trifluoromethyl enones, phosphine oxides, and alcohols in water solution is developed. This defluorinative occurs through a cascade process involving defluorophosphorylation, defluoroalkyloxylation, defluoroheteroannulation, enabling the modular synthesis furans with four distinct substituents: C2-alkyloxy, C3-trifluoromethyl, C4-phosphoryl, C5-(hetero)aryl groups. Moreover, apart from alcohol substrates, scope nucleophiles could be further extended to phenols, azacycles, or sulfonamide.

Language: Английский

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Sequential C−F Bond Transformation of the Difluoromethylene Unit in Perfluoroalkyl Groups: A Combination of Fine‐Tuned Phenothiazine Photoredox Catalyst and Lewis Acid

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(14)

Published: Feb. 21, 2024

A sequential process via photoredox catalysis and Lewis acid mediation for C-F bond transformation of the CF

Language: Английский

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Intermolecular Defluorinative 1,2-Diamination of Fluoroalkenyl Iodides with Sulfonamides: Synthesis of Acyclic and Cyclic Fluorinated 1,2-Enediamines

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 13, 2024

An intermolecular defluorinative vicinal diamination protocol employing fluoroalkenyl iodides and sulfonamides for the efficient synthesis of a series acyclic cyclic fluorinated 1,2-enediamines has been developed.

Language: Английский

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Nickel-catalysed chelation-assisted reductive defluorinative sulfenylation of trifluoropropionic acid derivatives

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(17), P. 2405 - 2408

Published: Jan. 1, 2024

Nickel-catalysed chelation-assisted reductive cross-coupling of trifluoropropanamides/esters with disulfides to afford thioacrylamides/esters high E selectivity, involving triple C–F bond cleavage.

Language: Английский

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Water-Involved 1,3-Aminoxylation of Fluoroalkenes: Chemo-, Regio-, and Stereoselective Synthesis of β-Fluoroacyl Vinylamines

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

Published: April 9, 2025

Perfluoroalkyl alkenyl iodides (PFAIs) are emerging as highly reactive, storage-stable, and multifunctional fluoroalkyl-bearing reagents, facilitating the manufacture of value-added organofluorides through multi-halo-functionalization. Herein, we developed a water-involved 1,3-aminoxylation PFAIs with sulfonamides for chemo-, regio-, Z-stereoselective synthesis valuable β-fluoroacyl vinylamines. This reaction proceeded via sequential deiodoamination defluoroxylation process under transition-metal-free conditions, featuring broad substrate scope good functional group tolerance. Compared to reported methods, some drawbacks, such multistep manipulation, harsh need expensive catalysts, use toxic/sensitive could be eliminated. Furthermore, synthetic potential this method was demonstrated scale-up synthesis, postfunctionalization complex molecules, ready transformation products.

Language: Английский

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Ammonium Salts as Convenient Ammonia Surrogates in the Willgerodt Reaction

Russian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 61(3), P. 561 - 566

Published: March 1, 2025

Language: Английский

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Sulfonylation of 2-Haloquinolines with Sulfonyl Hydrazides in Water for Accessing 2-Sulfonyl Quinolines under Catalyst-, Reductant-, and Additive-Free Conditions

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134705 - 134705

Published: May 1, 2025

Language: Английский

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