“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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EDA Complex-Enabled Annulation to Access CF₂-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10614 - 10623

Published: July 25, 2024

A photocatalyst-free and EDA complex-enabled radical cascade cyclization reaction of inactive alkenes with bromodifluoroacetamides was reported for the divergent synthesis fluorine-containing tetralones quinazolinones. In this transformation, persulfates as electron donors difluoro bromamide acceptors generate complex. This is a promising photochemical method advantages such mild conditions, simple operation, being metal-free, excellent functional group tolerance.

Language: Английский

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Synthesis of 2‐(β‐Trifluoromethyl‐β‐arylethylthio)pyridine through DBU‐Mediated Regioselective Addition of Pyridine‐2(1H)‐thione Onto α‐(Trifluoromethyl)styrenes

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(3)

Published: Jan. 8, 2024

Abstract An efficient and practical method for the synthesis of (β‐trifluoromethyl‐β‐aryl)ethyl 2‐pyridyl thioethers via hydrothiolation α‐(trifluoromethyl)styrenes with pyridine‐2(1 H )‐thione was reported. The reaction proceeded smoothly regioselectively in an anti‐Markovnikov manner assistance DBU afforded a variety trifluoromethyl‐containing moderate to good yields.

Language: Английский

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Air‐Induced Hydroxyphosphorylation of α‐Trifluoromethyl Styrenes with H‐Phosphonates and H‐Phosphine Oxides

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: unknown

Published: Aug. 22, 2023

Abstract Efficient synthesis of β‐hydroxy‐β‐CF 3 ‐phosphonates and ‐phosphine oxides by Mn‐mediated or transition‐metal‐free hydroxyphosphorylation α‐trifluoromethy)styrenes with H the assistance air, respectively, was described.

Language: Английский

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Two-step synthesis of vicinal trifluoromethyl primary amines from α-(trifluoromethyl)styrenes and phthalimide

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(23), P. 4641 - 4646

Published: Jan. 1, 2024

A novel two-step synthesis of β-trifluoromethyl primary amines from readily available α-(trifluoromethyl)styrenes and phthalimide is developed. The first step involves a hydroamination between (PhthNH) with the assistance base. Next, hydrazinolysis resulting

Language: 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, Journal Year: 2023, Volume and Issue: 365(20), P. 3546 - 3552

Published: Sept. 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

Language: Английский

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Facile synthesis of β‐trifluoromethyl thioethers via DBN‐catalyzed hydrothiolation of a‐trifluoromethyl styrenes with thiols

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(20)

Published: July 23, 2024

Abstract A very simple and atom‐economical method for the synthesis of vicinal trifluoromethyl thioethers via DBN‐catalyzed hydrothiolation α‐(trifluoromethyl)styrenes with thiols was reported. The reaction proceeded smoothly under mild conditions provided β‐CF 3 ‐thioethers in moderate to good yields an anti‐Markovnikov manner. Furthermore, this features several remarkable advantages, such as use a catalytic amount DBN, broad substrate scope, excellent functional group compatibility, easy scalability.

Language: Английский

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Efficient synthesis of functionalized trifluoromethyl cyclopropanes via cyclopropanation of α-trifluoromethyl styrenes with chloroacetonitrile and ethyl chloroacetate

New Journal of Chemistry, Journal Year: 2023, Volume and Issue: 47(35), P. 16604 - 16610

Published: Jan. 1, 2023

A practical method for the synthesis of functionalized trifluoromethyl cyclopropanes via cyclopropanation α-trifluoromethyl styrenes with chloroacetonitrile or ethyl chloroacetate was developed.

Language: Английский

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Tunable base-controlled chemoselective synthesis of trifluoromethyl-containing N-substituted benzimidazole-2-thiones and monofluorinated 4H-benzo[4,5]imidazo[2,1-b][1,3]thiazine

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

A base-controlled synthesis of N -β-CF 3 -substituted 2 H -benzo[ d ]imidazole-2-thiones and 2-fluoro-4 -benzo[4,5]imidazo[2,1- b ][1,3]thiazines via hydroamination or defluorinative cyclizations α-CF -styrenes with 2-mercaptobenzimidazole was developed.

Language: Английский

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