Base-controlled selective cleavage of the C–F bond of difluorocarbene for the divergent assembly of indolizines

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4214 - 4218

Опубликована: Янв. 1, 2024

A [3 + 1 1] cascade annulation reaction for the divergent construction of trisubstituted indolizines using sulfoxonium ylides, BrCF 2 CO Me and pyridinium salts as readily available substrates has been developed.

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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Copper‐Catalyzed Oxidative Trifluoromethylation of Aromatic Alkenes for the Synthesis of α‐Trifluoromethylated Ketones

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(3)

Опубликована: Янв. 23, 2024

Abstract A copper‐catalyzed oxidative trifluoromethylation of aromatic alkenes has been developed successfully, providing access to a variety valuable α‐trifluoromethyl‐substituted ketones using Togni's reagent as the trifluoromethyl source. The use affordable copper catalyst and readily available feedstock, broad substrate scope, mild conditions, operational simplicity are attractive features method. Preliminary mechanistic studies revealed that both dimethyl sulfoxide (DMSO) air might function oxidant for transformation.

Язык: Английский

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Advances in the Synthesis of α-Trifluoromethyl Ketones and Their Application via Defluorinative Reactions

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(1), С. 86 - 86

Опубликована: Янв. 1, 2025

Язык: Английский

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Synthesis of Functionalized Indolizines through 1,3-Dipolar Cycloaddition of Zwitterionic Ketenimines and Pyridinium Salts

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 19, 2025

A straightforward and efficient strategy for the synthesis of fully functionalized indolizines has been developed through a transition metal- oxidant-free [3 + 2] cycloaddition reaction zwitterionic ketenimines pyridinium salts. This versatile method proceeds under mild conditions, affording in moderate to good yields. approach involves an intermolecular cycloaddition, followed by enamine/imine tautomerization aromatization. Notably, this demonstrates broad functional group compatibility allows facile scalability, making it valuable tool indolizine-based frameworks organic medicinal chemistry.

Язык: Английский

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Synthesis of 2-Fluorinated Pyrazolo[1,5-a]pyridines via Base- Mediated [3+2] Cycloaddition of N-Aminopyridinium Salts with gem-Difluorostyrenes

New Journal of Chemistry, Год журнала: 2024, Номер 48(28), С. 12496 - 12500

Опубликована: Янв. 1, 2024

A method for the construction of 2-fluoropyrazolo[1,5- a ]pyridines through base-promoted [3+2] cycloaddition N -aminopyridinium salts with gem -difluorostyrenes has been established.

Язык: Английский

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Highly diastereoselective multicomponent synthesis of 2-piperidone-substituted pyridinium salts with three and four stereogenic centers

Tetrahedron, Год журнала: 2023, Номер 149, С. 133685 - 133685

Опубликована: Окт. 14, 2023

Язык: Английский

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1,2-Oxidative Trifluoromethylation of Olefin with Ag(O2CCF2SO2F) and O2: Synthesis of α-Trifluoromethyl Ketones

Molecules, Год журнала: 2024, Номер 29(23), С. 5622 - 5622

Опубликована: Ноя. 27, 2024

A novel and efficient 1,2-oxidative trifluoromethylation of olefins employing Ag(O2CCF2SO2F) as a trifluoromethyl source is described with O2 the oxidant, which provides access to variety valuable α-trifluoromethyl-substituted ketones. The broad substrate scope, feasibility large-scale operation, derivatization reactions α-trifluoromethyl ketones demonstrate promising utility this protocol.

Язык: Английский

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β,β-Difluoro Peroxides as Fluorinated C2-Building Blocks for the Construction of Functionalized Indolizines

Molecules, Год журнала: 2024, Номер 29(24), С. 5927 - 5927

Опубликована: Дек. 16, 2024

An effective method for the construction of functionalized indolizines has been developed in which β,β-difluoro peroxides act as novel C2-building blocks to implement [3+2] annulation with pyridinium ylides under base-mediated conditions. With this protocol, a broad range multisubstituted were prepared moderate good yields mild conditions, and many useful functional groups tolerated.

Язык: Английский

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