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

---

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

---

Palladium-catalyzed decarboxylation [2 + 2 + 2] annulation approach to chromone-containing polycyclic compounds

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(15), С. 3752 - 3759

Опубликована: Янв. 1, 2023

A variety of chromone-containing polycyclic compounds are efficiently generated via Pd-catalyzed decarboxylation [2 + 2 2] annulation 3-iodochromones, bridged olefins and o-bromobenzoic acids, in which o -bromobenzoic acids were employed as the electrophilic aryl units.

Язык: Английский

---

Oxoammonium-Catalyzed Ether Oxidation via Hydride Abstraction: Methodology Development and Mechanistic Investigation Using Paramagnetic Relaxation Enhancement NMR

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(46), С. 31420 - 31432

Опубликована: Ноя. 11, 2024

Hydride abstraction represents a promising yet underexplored approach in the functionalization of C-H bonds. In this work, we report oxidation α-C-H bonds ethers via oxoammonium catalysis using 3-chloroperbenzoic acid (

Язык: Английский

---

Recent Advances in Nickel‐Catalyzed Synthesis of Allenes: New Insights and Perspectives

ChemCatChem, Год журнала: 2023, Номер 15(19)

Опубликована: Июль 17, 2023

Abstract Allenes are one of the most important functional groups in organic chemistry, featuring unique physical and chemical properties. They not only key scaffolds present natural products, pharmaceutical molecules, advanced materials, but also valuable versatile building blocks for construction various complex bioactive molecules synthesis. Accordingly, benefiting from rapid development transition metal catalysis, numerous remarkable efficient approaches synthesis allenes readily available chemicals have been established past decades. In this brief review, we focus on recent advancements nickel‐catalyzed allenes. These transformations divided into two categories according to types reactions sorted further by starting materials. Moreover, a concise discussion limitations potential areas improvement field is provided, which would give an inspiration future study allene

Язык: Английский

---

Hydride Transfer-Enabled Dearomative Spirocyclization of Isoxazoles with O-Alkyl ortho-Oxybenzaldehydes

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 17, 2025

The TfOH-catalyzed dearomative [5 + 1] annulations were developed for the construction of chromane-fused spiroisoxazolines from readily available 5-amino-isoxazoles and O-alkyl ortho-oxybenzaldehydes. "two-birds-with-one-stone" strategy featuring dearomatization α-C(sp3)–H bond functionalization oxygen was disclosed via a cascade condensation/[1,5]-hydride transfer/dearomative spirocyclization process. In addition, unprecedented direct isoxazoles achieved, which introduced new family member chemistry.

Язык: Английский

---

Palladium-catalyzed chemoselective N-monoallylation of aromatic amines with diallylamine through a borrowing hydrogen strategy

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134648 - 134648

Опубликована: Апрель 1, 2025

Язык: Английский

---

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

---

Dearomatization of 3-Aminophenols for Synthesis of Spiro[chromane-3,1′-cyclohexane]-2′,4′-dien-6′-ones via Hydride Transfer Strategy-Enabled [5+1] Annulations

Molecules, Год журнала: 2024, Номер 29(5), С. 1012 - 1012

Опубликована: Фев. 26, 2024

The Sc(OTf)3-catalyzed dearomative [5+1] annulations between readily available 3-aminophenols and O-alkyl ortho-oxybenzaldehydes were developed for synthesis of spiro[chromane-3,1′-cyclohexane]-2′,4′-dien-6′-ones. “two-birds-with-one-stone” strategy was disclosed by the dearomatization phenols direct α-C(sp3)–H bond functionalization oxygen through cascade condensation/[1,5]-hydride transfer/dearomative-cyclization process. In addition, antifungal activity assay derivatizations products conducted to further enrich utility structure.

Язык: Английский

---

Iodomethane in C1 chemistry: application in palladium-catalyzed [2 + 2 + 1] annulation

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(16), С. 3204 - 3208

Опубликована: Янв. 1, 2024

An efficient palladium-catalyzed [2 + 2 1] annulation of 3-iodochromones, bridged olefins, and iodomethane is described, affording a range chromone-containing polycyclic compounds. Additionally, the corresponding deuterated products were smoothly obtained with iodomethane-

Язык: Английский

---