Merging dearomatization with redox-neutral C(sp³)–H functionalization via hydride transfer/cyclization: recent advances and perspectives

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(18), С. 5041 - 5052

Опубликована: Янв. 1, 2022

This review highlights the encouraging advances in hydride transfer-involved dearomatization reaction during past decade, content of which is categorized according to acceptors, namely vinylogous imines and quinone methides.

Язык: Английский

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Controllable Synthesis of N-Heterocycles via Hydride Transfer Strategy-Enabled Formal [5 + 1] and [5 + 2] Cyclizations

Organic Letters, Год журнала: 2023, Номер 26(1), С. 332 - 337

Опубликована: Дек. 28, 2023

The Brønsted acid-controlled switchable synthesis of indoline-fused tetrahydroquinolines and indole-fused benzazepines was developed through hydride transfer-enabled formal [5 + 1] 2] cyclization reactions from indoles N-alkyl o-aminobenzoketones. Indoline, furanone, tetrahydroquinoline hybridized pentacyclic products were unprecedentedly accessed via a cascade condensation/hydride transfer/dearomatization-cyclization/deethylation/nucleophilic addition process. In addition, the undeveloped transfer-involved cyclizations also realized for direct construction benzazepines.

Язык: Английский

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Divergent synthesis of nitrogen heterocyclesviaH₂O-mediated hydride transfer reactions

Green Chemistry, Год журнала: 2023, Номер 25(13), С. 5134 - 5141

Опубликована: Янв. 1, 2023

The H 2 O-promoted controllable synthesis of diverse 3-carboxyl and 3-acyl substituted tetrahydroquinolines 3,4-dihydroquinolin-2(1 )-ones from readily available feedstocks was developed by a hydride transfer strategy.

Язык: Английский

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Alkyl amines and ethers as traceless hydride donors in [1,5]-hydride transfer cascade reactions

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(4), С. 700 - 714

Опубликована: Янв. 1, 2023

The use of alkyl amines and ethers as traceless hydride donors in [1,5]-hydride transfer cascade reactions has been reviewed herein.

Язык: Английский

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Synthesis spiro and fused chromenes via [4 + 2] cycloaddition of salicyl N-tosylimines and cyclic dienophiles

Journal of Molecular Structure, Год журнала: 2024, Номер 1304, С. 137684 - 137684

Опубликована: Фев. 4, 2024

Язык: Английский

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Visible-Light-Catalyzed Fast Synthesis of 1,4-Benzoxazepine Derivatives from 2-Alkoxyarylaldehydes and N-Arylglycines

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 3, 2025

A novel photocatalytic method for the synthesis of 1,4-benzoxazepine using 2-alkoxyarylaldehyde as an oxygen source and N-arylglycine a nitrogen has been reported. This is mild, efficient, fast, corresponding reaction can be completed within 2 h at room temperature under atmosphere light-irradiation conditions. Mechanistic studies have confirmed that this scheme involves decarboxylation cyclization provides convenient pathway preparation various 2-alkyl-N-phenyl-substituted 1,4-benzoxazepine.

Язык: Английский

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Role of Hydrogen Transfer in Functional Molecular Materials and Devices

Precision Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 11, 2025

Язык: Английский

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HFIP-mediated three-component imidization of electron-rich arenes with in situ formed spiroindolenines for facile construction of 2-arylspiroindolenines

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(6), С. 1696 - 1702

Опубликована: Янв. 1, 2022

The three-component reaction of o -aminobenzaldehydes with 5-hydroxyindole and electron-rich arenes has been achieved through HFIP-mediated cascade hydride transfer/dearomative cyclization/CDC-type imidization at room temperature under air.

Язык: Английский

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Aromatization-driven cascade [1,5]-hydride transfer/cyclization for synthesis of spirochromanes

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(7), С. 1796 - 1802

Опубликована: Янв. 1, 2023

An aromatization-driven hydride transfer-involved α-C(sp 3 )–H bond functionalization of the oxygen atom was developed. Easily prepared p -quinone methides were applied to initiate [1,5]-hydride transfer/cyclization for generating spirochromanes.

Язык: Английский

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1,7-Hydride transfer-involved dearomatization of quinolines to access C3-spiro hydroquinolines

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Фев. 1, 2024

1,7-Hydride transfer-involved dearomatization of quinolines toward C3-spiro hydroquinoline derivatives has been developed. This method offers a protocol to achieve the electron-deficient arenes via redox-neutral hydride transfer process. A series hydroquinolines can be provided in moderate excellent yields (up 98%) with good diastereoselectivities. Significant advantages such as high step- and atom-economy, well mild conditions, make it an appealing alternative quinolines.

Язык: Английский

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