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

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(14), С. 3974 - 3981

Опубликована: Янв. 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.

Язык: Английский

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Water-promoted defluorinative synthesis of fluoroalkylated 1,5-diazapentadienes by using (NH₄)₂CO₃ as an NH₂ and NH source

Green Chemistry, Год журнала: 2023, Номер 25(23), С. 9672 - 9679

Опубликована: Янв. 1, 2023

A H 2 O-promoted and (NH 4 ) CO 3 -enabled defluoroiminization reaction of fluoroalkyl alkenes for the synthesis fluoroalkylated 1,5-diazapentadienes has been developed.

Язык: Английский

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Sequential In Situ-Formed Kukhtin–Ramirez Adduct and P(NMe₂)₃-Catalyzed O-Phosphination of α-Dicarbonyls with P(O)–H

Organic Letters, Год журнала: 2023, Номер 25(42), С. 7595 - 7600

Опубликована: Окт. 13, 2023

O-Phosphination of α-dicarbonyls via sequential in situ formation a Kukhtin-Ramirez adduct and P(NMe2)3-catalyzed process has been exploited for the synthesis α-phosphoryloxy carbonyls. A range P(O)-H derivatives, including diarylphosphine oxides, arylphosphinates, phosphinates, are competent candidates to be introduced into this transformation, various carbonyls obtained. This approach possesses advantages mild conditions, simple operations, atom economy, high efficiency, gram-scale synthesis, which make it promising toolbox.

Язык: Английский

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TEMPO/PhI(OAc)₂ promotes the α-aminophosphinoylation of alcohols with amines and H-phosphine oxides in aqueous medium

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(19), С. 3860 - 3865

Опубликована: Янв. 1, 2024

The aminophosphinoylation of alcohols with amines and H-phosphine oxides provides an efficient mild approach to access various α-aminoalkylphosphine in good yields tolerance functional groups using H 2 O as a clean solvent.

Язык: Английский

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Combining Hydrodefluorination and Defluorophosphorylation for Chemo- and Stereoselective Synthesis of gem-Fluorophosphine Alkenes

Organic Letters, Год журнала: 2023, Номер 25(34), С. 6368 - 6373

Опубликована: Авг. 18, 2023

A chemo-, regio-, and stereoselective reaction of trifluoromethyl enones, phenylsilane, phosphine oxides through a sequential hydrodefluorination defluorophosphorylation relay is developed for the synthesis distinctive gem-fluorophosphine alkenes. This multicomponent occurred under transition-metal-free conditions with good functional group tolerance. Moreover, preinstalled carbonyl auxiliary important tuning reactivity β-trifluoromethyl thereby enabling controllable selective functionalization two fluorine atoms in trifluoromethylated enones.

Язык: 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, Год журнала: 2025, Номер unknown, С. 134705 - 134705

Опубликована: Май 1, 2025

Язык: Английский

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Transition‐Metal‐Free Carbonyl Reduction and Hydrodefluorination of β‐Trifluoromethyl Enones with Hydrosilanes: Synthesis of gem‐Difluorovinyl Alcohols

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(23)

Опубликована: Апрель 20, 2024

Abstract A tandem carbonyl reduction and hydrodefluorination of β‐trifluoromethyl enones with hydrosilanes under transition‐metal‐free conditions was developed for the synthesis a variety valuable gem ‐difluorovinyl alcohols. The hydrosilane could act as both reductive agent C(sp 3 )‐F bond‐breaking promoter mild reaction conditions. Synthetically useful organofluorides, such ‐fluorophosphine alkene, ketone, fluorinated dihydrofuran derivatives be readily constructed by further transformations obtained Moreover, method features conditions, operational simplicity, excellent functional group tolerance, scalability.

Язык: Английский

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Nickel-Catalyzed Hydrodefluorination/Deuterodefluorination of CF3-alkenes with Formic Acid

Chemical Communications, Год журнала: 2024, Номер 60(51), С. 6548 - 6551

Опубликована: Янв. 1, 2024

The synthesis of deuterated

Язык: Английский

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“On‐Water” Synthesis of Sterically Congested γ‐Ketophosphine Oxides Featuring a CF₃‐ and P(O)‐Tetrasubstituted Carbon Center

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(20), С. 3546 - 3552

Опубликована: Сен. 16, 2023

Abstract The distinctive hydrophobic hydration effect in the aqueous solution contributes to success of phospha‐Michael reaction between β‐CF 3 ‐β,β‐disubstituted enones and diarylphosphine oxides, providing an access biologically relevant γ‐ketophosphine oxides bearing a sterically highly congested CF ‐ P(O)‐tetrasubstituted carbon center. More importantly, resulting products could be further transformed into densely functionalized containing

Язык: Английский

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Synthesis of gem-Difluorohomoallyl Amines via a Transition-Metal-Free Defluorinative Alkylation of Benzyl Amines with Trifluoromethyl Alkenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8342 - 8356

Опубликована: Май 31, 2024

A mild and transition-metal-free defluorinative alkylation of benzyl amines with trifluoromethyl alkenes is reported. The features this protocol are easy-to-obtain starting materials, a wide range substrates, functional group tolerance as well high atom economy, thus offering strategy to access variety

Язык: Английский

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