“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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Multi-functionalization of β-trifluoromethyl enones enabled 2,3-dihydrofuran synthesis

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5144 - 5150

Published: Jan. 1, 2024

A transition-metal-free multi-functionalization reaction of β-trifluoromethyl enones and azacycles is first developed for the synthesis valuable amino-2,3-dihydrofuran derivatives.

Language: Английский

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Palladium-Catalyzed Regioselective Monofluoroallylation of Indoles with gem-Difluorocyclopropanes

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6905 - 6909

Published: Aug. 1, 2024

We present a palladium-catalyzed ring-opening reaction that induces indoles to cross-couple with gem-difluorocyclopropanes. The proceeds through domino process of C–C bond activation and C–F elimination, followed by C–C(sp2) coupling produce various 2-fluoroallylindoles. This method is characterized its high functional group tolerance, good yields regioselectivity, under base-free conditions. synthetic utility the products illustrated functionalization NH C2 positions indole scaffold.

Language: Английский

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Controlled Defluorinative Carboxylation Cascade of Sterically Hindered CF₃-Alkenes with Formate Salt via Photocatalysis

Organic Letters, Journal Year: 2025, Volume and Issue: 27(10), P. 2492 - 2497

Published: March 5, 2025

A controlled cleavage of double C-F bonds in sterically hindered tetrasubstituted CF3-alkenes using formate salt has been achieved through a photoinduced electron transfer approach. Diverse γ-branched multifunctionalized gem-difluoroalkenes and α-fluoroacrylic acids are obtained sequentially via hydrodefluorination bond carboxylation with good-to-high yields. Precisely controlling the quantity reaction time is crucial for obtaining divergent defluorinative products. Formate serves as C1 source, hydrogen donor, reducing agent.

Language: Английский

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

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(51), P. 6548 - 6551

Published: Jan. 1, 2024

The synthesis of deuterated

Language: 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, Journal Year: 2024, Volume and Issue: 27(23)

Published: April 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.

Language: Английский

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β-Trifluoromethylated enones as trifluoromethylated synthons in asymmetric catalysis

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(21), P. 5519 - 5537

Published: Jan. 1, 2023

This minireview describes the applications of β-trifluoromethylated enones in diverse asymmetric catalytic transformations since 2008, and incorporates mechanistic aspects, involving key intermediates reaction pathways.

Language: Английский

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Photoinduced Transition‐Metal‐Free Chemodivergent Phosphorylation‐Peroxidation and Oxyphosphorylation of Alkenes

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 22, 2024

Abstract A visible‐light‐promoted chemodivergent phosphorylation‐peroxidation and oxyphosphorylation of alkenes with phosphine oxides HOO t Bu was realized under transition‐metal‐free conditions. Using the commercially available Eosin Y as a SET‐photocatalyst, β ‐peroxy‐phosphine were selectively obtained catalytic amount base, while addition acid led to exclusive formation ‐keto‐phosphine control experiments showed that could also act HAT‐catalyst induce O−O bond cleavage peroxides acidic

Language: Английский

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Transition-Metal-Free Hydrodefluoroamination of Trifluoromethyl Enones for the Synthesis of α-Fluoroenamides

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10299 - 10310

Published: July 2, 2024

A three-component strategy was developed to enable hydrodefluoroamination of β-trifluoromethyl enones by selectively activating two C(sp3)-F bonds in the trifluoromethyl group. The method involved a sequence carbonyl reduction, hydrodefluorination, and defluoroamination under transition-metal-free conditions. Synthetically useful (E)-stereospecific α-fluoroenamides were obtained good yields with diverse functional group tolerance, which could be easily transformed into valuable organofluorides heterocycles. auxiliary exerts both electronic steric impacts on CF3-alkenes, allowing for controllable selective defluorination.

Language: Английский

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