Controllable Fluorocarbon Chain Elongation: TMSCF₂Br-Enabled Trifluorovinylation and Pentafluorocyclopropylation of Aldehydes

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(3), С. 1806 - 1812

Опубликована: Янв. 9, 2024

Controllable fluorocarbon chain elongation (CFCE) is a promising yet underdeveloped strategy for the well-defined synthesis of structurally novel polyfluorinated compounds. Herein, direct and efficient trifluorovinylation pentafluorocyclopropylation aldehydes are described by using TMSCF

Язык: Английский

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Visible-light-induced [1,3]-brook rearrangements of α-ketoacylsilanes and their subsequent trapping in a tandem annulation with 1,3,5-triazinanes and azomethine imines

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(11), С. 3250 - 3256

Опубликована: Янв. 1, 2024

An unusual visible-light-induced [1,3]-brook rearrangement of α-ketoacylsilanes for cascade cyclization with 1,3,5-triazinanes and C , N -cyclic azomethine imines has been realized to assemble various β-lactams pyrazolidinone scaffolds.

Язык: Английский

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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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Synthesis of gem-Difluorinated 2,3-Dihydrobenzofurans Using Freon-22 via [4 + 1] Annulation of Difluorocarbene and Antitumor Activity Evaluation

Organic Letters, Год журнала: 2024, Номер 26(6), С. 1212 - 1217

Опубликована: Фев. 1, 2024

As an inexpensive industrial chemical, chlorodifluoromethane (Freon-22), despite its relatively low reactivity, can serve as a practical CF

Язык: Английский

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Advances in the Synthetic Utility of Difluorocarbene Generated from TMSCF₃ (Ruppert‐Prakash Reagent) and Its Derivatives

The Chemical Record, Год журнала: 2025, Номер unknown

Опубликована: Март 12, 2025

Abstract Organofluorine compounds are of pivotal significance particularly, in drug and agrochemical industries different strategies have been designed for their synthesis. The last two decades witnessed the emergence difluorocarbene as an efficient synthetic tool, providing easy access to organofluorine compounds. This review summarises reactions generated from Ruppert‐Prakash reagent (TMSCF 3 ) its derivatives TMSCF 2 Cl Br. Among various fluorination techniques available, chemistry offers a cost effective procedure, opening avenue large number details developments utility derivatives, till date.

Язык: Английский

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Construction of a 1,2-diazetidine core based on a multicomponent reaction of N,N′-(2,3-dimethylbutane-2,3-diyl)bis(hydroxylamine), arylglyoxals, and Meldrum's acid

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

In the present paper we describe first example of construction a 1,2-diazetidine core based on vicinal bis(hydroxylamine).

Язык: Английский

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Difluorocarbene Enables Access to 2,2-Difluorohydrobenzofurans and 2-Fluorobenzofurans from ortho-Vinylphenols

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3744 - 3749

Опубликована: Апрель 30, 2024

2-Fluorobenzofurans are the backbone structures of many drug molecules and have potential therapeutic bioactivities. Despite applications in medicinal chemistry, practical efficient synthetic methods for construction 2-fluorobenzofuran very limited. Herein, we report an general method 2-fluorobenzofurans. Contrary to previous functionalizations existing benzofuran, our strategy directly constructs benzofuran scaffolds alongside incorporation fluorine atom on C2 position a formal [4 + 1] cyclization from readily accessible

Язык: Английский

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Difluorocarbene in Cycloadditions and Annulations for the Synthesis of gem‐Difluorocarbocycles and gem‐Difluoroheterocycles

European Journal of Organic Chemistry, Год журнала: 2023, Номер 27(3)

Опубликована: Ноя. 13, 2023

Abstract Difluorocarbene is a simple, readily prepared, and versatile difluorinated one‐carbon synthon. It can be applied as both the difluoromethylating reagent in carbene insertion difluoromethylenating various cycloadditions annulations. This concept article provides an account of applications difluorocarbene annulations for synthesis gem ‐difluorocarbocycles ‐difluoroheterocycles. The synthesized include 2,2‐difluorobicyclo[1.1.1]pentanes, 4,4‐/5,5‐difluoro‐cyclopentenes, 2,2‐difluorocyclopentanones, 5,5‐difluorocyclopent‐2‐enones via tandem [2+1] cycloaddition ring‐expansion or [4+1] prepared ‐difluoroheterocycles involve 2,2‐/3,3‐difluoro‐2,3‐dihydrofurans, 2,2‐difluoro‐2,3‐dihydrobenzofurans, 2,2‐difluoro‐2,3‐dihydrobenzothiophenes, 2,2‐difluorobenzofuran‐3(2 H )‐ones, 2,2‐difluorobenzothiophen‐3(2 2,2‐difluoro‐2,3‐dihydrothieno[2,3‐ b ]pyridines, 2,2‐difluorothieno[2,3‐ ]pyridine‐3(2 5,5‐difluorooxazolines thiazolines, spirocyclic 2,2‐difluorobenzo[ d ][1,3]aza/phosphaborol‐1‐ium‐3‐yliums annulations, 1,1‐difluoro‐1,4,5,9b‐tetrahydro‐2 ‐[1,2]diazeto[4,1‐ ]isoquinolines ‐[1,2]diazeto[1,4‐ ]pyrrolo[2,1‐ c ]pyrazines [3+1] annulation, 1,1‐difluoro‐1,9a‐dihydropyrido[2,1‐ ][1,4]thiazines 3,3‐difluorobenzo[ e ][1,4,2]oxaza/phosphaborinin‐4‐ium‐2‐uides [5+1] 9,9‐difluoro‐8‐azabicyclo[5.2.0]nona‐2,4,6‐trienes [8+1] 4,4‐difluorooxazolidines 3,3‐difluoropyrrolidines [2+2+1] generated from different available precursors proceeds these well. substrate scopes, proposed mechanisms, selected product examples their are discussed.

Язык: Английский

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Synthesis of α,α-Difluoromethylene Amines from Thioamides Using Silver Fluoride

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 18, 2024

We developed a mild, rapid process employing AgF and thioamides to produce α,α-difluoromethylene amines efficiently. This method exhibited remarkable tolerance toward various functional groups present in

Язык: Английский

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General access to furan-substituted gem-difluoroalkenes enabled by PFTB-promoted cross-coupling of ene-yne-ketones and difluorocarbene

Chemical Science, Год журнала: 2024, Номер 16(3), С. 1455 - 1464

Опубликована: Дек. 23, 2024

An efficient method for the tandem cyclization cross-coupling of conjugated ene-yne-ketones with difluorocarbene via PFTB promotion is described, providing facile access to diverse furan-substituted difluoroalkenes potential antitumor potency.

Язык: Английский

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