Multiple-fold C–F bond functionalization for the synthesis of (hetero)cyclic compounds: fluorine as a detachable chemical handle

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(7), С. 2013 - 2055

Опубликована: Янв. 1, 2022

We highlighted the recent advances in field of multiple-fold C–F bond functionalization for synthesis (hetero)cyclic compounds.

Язык: Английский

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Chemo-, regio-, and stereoselective tetrafunctionalization of fluoroalkynes enables divergent synthesis of 5-7-membered azacycles

Chemical Science, Год журнала: 2024, Номер 15(30), С. 12026 - 12035

Опубликована: Янв. 1, 2024

A 1,2,3,4-tetrafunctionalization of polyfluoroalkynes for the divergent construction 5-7-membered ( E )-1,2-difluorovinyl azacycles is developed.

Язык: Английский

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Perfluoroalkyl Editing of Fluoroalkynes: Chemo-, Regio-, and Stereoselective Synthesis of (E)-(2-Amino-fluoroalkenyl)pyrimidines

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 26, 2025

A chemo-, regio-, and stereoselective condensation reaction of perfluoroalkyl alkynes (PFAAs), (CH2O)n, (NH4)2CO3 through the cleavage five inert C(sp3)-F bonds at three distinct carbon sites, thereby establishing an unprecedented platform for synthesizing structurally unique (E)-(2-amino-fluoroalkenyl)pyrimidines, is first developed. Remarkably, this features mild conditions, good compatibility with various functional groups, excellent E-stereoselectivity, late-stage modification complex molecules, scalability, versatile synthetic transformations resulting heterocyclic compounds.

Язык: Английский

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Synthesis of CF₃-Substituted N-Heterocyclic Compounds Based on C–H Activation-Initiated Formal [2 + 3] Annulation Featuring with a Latent Nucleophilic Site

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7828 - 7842

Опубликована: Май 22, 2024

Presented herein is a novel synthesis of CF

Язык: Английский

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Experimental and computational journey on transition-metal-catalyzed C H functionalization with fluorinated π-systems

Coordination Chemistry Reviews, Год журнала: 2024, Номер 522, С. 216244 - 216244

Опубликована: Сен. 24, 2024

Язык: Английский

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Chemo-, Regio-, and Stereoselective Assembly of Polysubstituted Furan-2(5H)-ones Enabled by Rh(III)-Catalyzed Domino C–H Alkenylation/Directing Group Migration/Lactonization: A Combined Experimental and Computational Study

ACS Catalysis, Год журнала: 2021, Номер 11(22), С. 13921 - 13934

Опубликована: Ноя. 2, 2021

Exploring multistep cascade reactions triggered by C–H activation are recognized as appealing, yet challenging. Herein, we disclose a Rh(III)-catalyzed domino coupling of N-carbamoyl indoles and 4-hydroxy-2-alkynoates for the streamlined assembly highly functionalized furan-2(5H)-ones in which carbamoyl-directing group (DG) is given dual role an auxiliary migrating acylating reagent via cleavage stable C–N bonds at room temperature. More importantly, obtained furan-2(5H)-one skeleton could be further under air situ C5–H hydroxylation simply switching solvent or additive, providing fully substituted with installation alcohol-based C5 quaternary carbon center. Detailed experimental studies density functional theory calculations reveal that Rh(III)-mediated tandem activation/alkyne insertion/DG migration/lactonization accounts developed transformation to achieve high functionalities observed exclusive selectivity. The potential biological application class potent PPARγ ligands highlights synthetic utility methodology. This protocol endowed several salient features including efficient activation, excellent chemo-, regio-, stereoselectivity, bond-forming efficiency (e.g., two C–C C–O bonds), solvent- additive-controlled product selectivity, good functional-group compatibility, mild redox-neutral conditions.

Язык: Английский

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Recyclable rhodium-catalyzed C–H activation/[4 + 2] annulation with unconventional regioselectivity at ambient temperature: experimental development and mechanistic insight

Green Chemistry, Год журнала: 2022, Номер 24(18), С. 7012 - 7021

Опубликована: Янв. 1, 2022

A robust and convenient rhodium-catalyzed unconventionally regioselective C–H activation/[4 + 2] annulation for the synthesis of isoquinolones which are prevalent in natural products pharmaceuticals was developed.

Язык: Английский

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Synthesis of Indole-Fused Oxepines via C–H Activation Initiated Diastereoselective [5 + 2] Annulation of Indoles with 1,6-Enynes

Organic Letters, Год журнала: 2021, Номер 23(21), С. 8365 - 8369

Опубликована: Окт. 15, 2021

A rhodium-catalyzed diastereoselective formal [5 + 2] annulation of indoles with cyclohexadienone-containing 1,6-enynes has been established via indole 2,3-difunctionalization. The reaction, probably proceeding through tandem C2–H alkenylation and intramolecular Friedel–Crafts alkylation relay, provides rapid construction indole-fused oxepines in good to excellent yields a broad substrate scope. This method also features concomitant cis-hydrobenzo[b] oxepine scaffolds, core unit found numerous natural products important biological activities.

Язык: Английский

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Recent advances in the synthesis of benzo[b]thiophene fused polycyclic derivatives: Strategies and reactions

Chinese Chemical Letters, Год журнала: 2022, Номер 34(6), С. 108003 - 108003

Опубликована: Ноя. 13, 2022

Язык: Английский

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Formation of Fluorovinyl Spiro-[imidazole-indene] and α-Amino-β-naphthalenones via Rh(III)-Catalyzed Cascade C–H Functionalization

Organic Letters, Год журнала: 2022, Номер 24(38), С. 6940 - 6944

Опубликована: Сен. 21, 2022

An efficacious method for building fluorovinyl spiro-[imidazole-indene] and α-amino-β-naphthalenone skeletons synchronously has been shown to consist of Rh(III)-catalyzed C–H functionalization between 2H-imidazoles difluoromethylene alkynes. This protocol demonstrates a practical straightforward route installing fluorine elements in the envisioned position heterocyclic compounds.

Язык: Английский

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