Visible-Light-Induced Defluorinative α-C(sp³)–H Alkylation for the Synthesis of gem-Difluoroallylated α-Trifluoromethylamines

Organic Letters, Год журнала: 2023, Номер 25(51), С. 9124 - 9129

Опубликована: Ноя. 17, 2023

Herein, we describe a novel and efficient photoredox catalytic Cα radical addition/defluoroalkylation coupling reaction between α-trifluoromethyl alkenes N-trifluoroethyl hydroxylamine. A series of gem-difluoroallylated α-trifluoromethylamines were synthesized by the addition enabled 1,2-H shift in situ-generated radical. Notably, this protocol is distinguished its mild conditions, easy operation, excellent functional group tolerability.

Язык: Английский

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Diastereo- and Enantioselective Dearomative Reductive Aryl-Fluoroalkenylation of Indoles by Nickel Catalysis

ACS Catalysis, Год журнала: 2024, Номер 14(9), С. 6432 - 6439

Опубликована: Апрель 11, 2024

Herein, we disclose a nickel-catalyzed dearomative reductive aryl-fluoroalkenylation of indoles by defluorinative coupling with gem-difluoroalkenes. The catalytic protocol affords facile assembly various monofluoroalkene-containing polycyclic fused indolines bearing two contiguous carbon stereocenters in high diastereo- and enantioselectivities tolerance diverse functional groups.

Язык: Английский

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Pd-Catalyzed Asymmetric Intramolecular Dearomatizing Reductive Heck Reaction of Indoles

Organic Letters, Год журнала: 2024, Номер 26(18), С. 3739 - 3743

Опубликована: Апрель 29, 2024

An enantioselective Pd-catalyzed intramolecular dearomative reductive Heck reaction of N-(o-bromoaryl) indole-3-carboxamide is developed. By employing Pd(dba)2/SPINOL-based phosphoramidite as the chiral catalyst and HCO2Na hydride source, a series enantioenriched spiro indolines bearing vicinal stereocenters were afforded in moderate to good yields with excellent enantioselectivities. The formal tetrasubstituted alkene β-hydrogens therefore realized by inhibiting β-H elimination.

Язык: Английский

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Visible-Light-Induced Tandem Nickel-Catalyzed Heck Cyclization/Self-Promoted [2+2] Intermolecular Cycloaddition

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 12, 2025

Visible-light-induced transition metal (TM) catalysis has emerged as a new paradigm to discover unprecedented transformations. The reported nickel species TM photocatalysts are mainly involved in the homolysis of Ni(II) complex or alkyl halide activation. Herein, we describe that photoexcited could facilitate Heck cyclization by accelerating anti-β-hydride elimination. Meanwhile, tandem visible-light-induced substrate self-promoted intermolecular [2+2] photocycloaddition without assistance additional was discovered.

Язык: Английский

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Asymmetric dearomative reductive arylallylation of indoles with trifluoromethyl alkenes by nickel catalysis

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(23), С. 5940 - 5949

Опубликована: Янв. 1, 2023

Herein, we report an asymmetric dearomative reductive arylallylation of indoles with trifluoromethyl alkenes enabled by nickel catalysis to access structurally diverse gem -difluorovinyl-containing chiral polycyclic indolines.

Язык: Английский

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Synthesis of gem-Difluorohomoallyl Amines via a Transition-Metal-Free Defluorinative Alkylation of Benzyl Amines with Trifluoromethyl Alkenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8342 - 8356

Опубликована: Май 31, 2024

A mild and transition-metal-free defluorinative alkylation of benzyl amines with trifluoromethyl alkenes is reported. The features this protocol are easy-to-obtain starting materials, a wide range substrates, functional group tolerance as well high atom economy, thus offering strategy to access variety

Язык: Английский

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Synthesis of substituted (trifluoromethyl)alkenes: (Trifluoromethyl)alkylidenation of thioketones via CF3-thiiranes

Journal of Fluorine Chemistry, Год журнала: 2024, Номер 275, С. 110273 - 110273

Опубликована: Март 23, 2024

Язык: Английский

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Research Progress in the Synthesis of Azaindoline and Its Derivatives

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(4), С. 1106 - 1106

Опубликована: Янв. 1, 2024

The azaindoline skeleton exists in a wide range of bioactive molecules and natural products, has significant biological pharmaceutical activities.The synthesis these compounds attracted great attention from chemists.However, due to the electron-deficient nature pyridine ring where nitrogen atom is located, many traditional methods for indoline cannot effectively construct skeleton.In recent years, chemists have been exploring made some progress.According different reaction types, azaindolines years key mechanisms are reviewed discussed, future development prospect this research field prospected.

Язык: Английский

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Switchable divergent synthesis of chiral indole derivatives via catalytic asymmetric dearomatization of 2,3-disubstituted indoles

RSC Advances, Год журнала: 2024, Номер 14(22), С. 15591 - 15596

Опубликована: Янв. 1, 2024

A strategy allowing the switchable divergent synthesis of chiral indole derivatives was established via phosphoric acid-catalyzed asymmetric dearomatization 2,3-disubstituted indoles using naphthoquinone monoimines as electrophiles. The products were switched between indolenines and fused indolines according to post-processing conditions. Both two types obtained in good high yields with generally excellent enantioselectivities. NaBH4 found work a promoter well reductant cyclization process leading indolines.

Язык: Английский

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Silver-Catalyzed Dearomative [3+2] Spiroannulation of Aryl Oxamic Acids with Alkynes

Synthesis, Год журнала: 2024, Номер 56(20), С. 3191 - 3198

Опубликована: Июль 3, 2024

Abstract A silver-catalyzed dearomative decarboxylative [3+2] spiroannulation of aryl oxamic acids with alkynes is described. The reaction provides reliable access to a range azaspiro[4,5]trienones in moderate yields aqueous media. In addition, the exhibits broad substrate scope and good functional group compatibility.

Язык: Английский

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