Recent Advances in Electron Donor‐Acceptor (EDA)‐Complex Reactions involving Quaternary Pyridinium Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(10), С. 1538 - 1564

Опубликована: Март 6, 2023

Abstract Quaternary pyridinium compounds are valuable intermediates in organic synthesis, which have gained immense popularity the synthetic community. The application of transition metal or photoredox catalysis transforming quaternary into various C−C and C−X bonds is well established. A majority these methods require high temperatures, expansive catalysts, delicate conditions for successful execution. On other hand, use metal‐free photocatalysis‐free strategies constructing using derivatives has been sought‐after. In this context, electron‐donor‐acceptor (EDA)‐complex reactions emerged as a state‐of‐the‐art methodology, do not any photocatalyst their EDA‐complex photochemistry takes advantage electron‐acceptor ability derivatives, can quickly generate radical precursor via deaminative process. These newly generated useful several transformations. We hereby, review, discuss an area major progress mediated involving with mechanism, substrate scope, limitations. magnified image

Язык: Английский

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Divergent Geminal Alkynylation–Allylation and Acylation–Allylation of Carbenes: Evolution and Roles of Two Transition-Metal Catalysts

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(7), С. 4727 - 4740

Опубликована: Фев. 8, 2024

Cooperative bimetallic catalysis to access novel reactivities is a powerful strategy for reaction development in transition-metal-catalyzed chemistry. Particularly, elucidation of the evolution two transition-metal catalysts and understanding their roles dual are among most fundamental goals catalysis. Herein, three-component terminal alkyne, diazo ester, an allylic carbonate was successfully developed via cooperative Cu/Rh with Xantphos as ligand, providing highly efficient 1,5-enynes all-carbon quaternary center that can be used immediate synthetic precursors complex cyclic molecules. Notably, Meyer–Schuster rearrangement involved reactions using propargylic alcohols, resulting unprecedented acylation–allylation carbenes. Mechanistic studies suggested course Cu(I) species might aggregate some types Cu clusters nanoparticles (NPs), while Rh(II)2 precursor dissociate mono-Rh species, wherein NPs proposed responsible alkynylation carbenes work cooperation Xantphos-coordinated dirhodium(II) or Rh(I)-catalyzed alkylation.

Язык: Английский

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Mechanochemical-assisted decarboxylative sulfonylation of α,β-unsaturated carboxylic acids with sodium sulfinate salts

Green Chemistry, Год журнала: 2024, Номер 26(5), С. 2721 - 2729

Опубликована: Янв. 1, 2024

Herein, we report a mechanochemical-assisted decarboxylative sulfonylation of α,β-unsaturated carboxylic acids with sodium sulfinate salts using potassium iodide as an activator under water-assisted grinding conditions.

Язык: Английский

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Photoredox-Catalyzed 1,4-Peroxidation–Sulfonylation of Enynones: A Three-Component Radical Coupling Approach for the Synthesis of Highly Functionalized Allenes

Organic Letters, Год журнала: 2024, Номер 26(15), С. 2955 - 2959

Опубликована: Апрель 3, 2024

An Eosin Y-catalyzed visible light-promoted 1,4-peroxidation–sulfonylation of enynones was achieved to give tetrasubstituted allenes. The photoredox catalysis Y allowed the concomitant formation peroxy and sulfonyl radicals, where preferential radical addition alkene moiety resulted in subsequent α-keto radical–sulfonyl cross couplings. developed demonstrates a regioselective 1,4-diradical strategy, opening up new possibility diradical functionalization conjugate systems.

Язык: Английский

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Radical cascade cyclization of 1,n-enynes under photo/electrochemical conditions

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(22), С. 5735 - 5745

Опубликована: Янв. 1, 2023

During the past decade, photo- and electrochemical reactions proceeding via single-electron-transfer (SET) triggered radical pathways have emerged as an indispensable strategy for efficient formation of chemical bonds.

Язык: Английский

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Visible light-assisted chemistry of vinyl azides and its applications in organic synthesis

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(23), С. 4723 - 4743

Опубликована: Янв. 1, 2023

Vinyl azides have emerged as highly versatile precursors in organic synthesis due to their rich reactivity driven by the excellent leaving-group ability of molecular nitrogen. Over years, significant advancement has been achieved manipulation vinyl for construction C-C and C-X bonds. Typical methods involve application transition metals strong oxidants conversion into useful compounds employing harsh reaction conditions coupled with intense product purification. In this regard, visible light chemistry become one most exciting fields being mild, sustainable, often orthogonal conventional approaches. Visible light-induced reactions involving generate either 2H-azirines or iminyl radicals key intermediates, which may undergo further transformations form desired cyclic acyclic products. Herein, we provide synthetic transient intermediates biological significance under photocatalysis. We classified review two parts: (i) formation an radical intermediate (ii) 2H-azirine intermediate-based reactions.

Язык: Английский

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Visible light-induced bromine radical enhanced hydrogen atom transfer (HAT) reactions in organic synthesis

RSC Sustainability, Год журнала: 2024, Номер 2(8), С. 2169 - 2189

Опубликована: Янв. 1, 2024

This review describes the recent advancements in visible light-induced bromine radical enhanced hydrogen atom transfer (HAT) reactions organic synthesis.

Язык: Английский

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The literature of heterocyclic chemistry, part XXII, 2022

Advances in heterocyclic chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Язык: Английский

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Visible Light-Mediated Aza-Norrish–Yang Type Cyclization

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 6473 - 6485

Опубликована: Апрель 6, 2025

Язык: Английский

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Visible-Light-Initiated Catalyst-Free Radical Annulation Reactions of 1,6-Enynes and Aryl Sulfonyl Bromide to Assemble Sulfonation/Bromination Succinimide Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(6), С. 3857 - 3867

Опубликована: Фев. 22, 2024

In the present study, environment-friendly visible-light-promoted strategy is used to perform an efficient, simple, and straightforward photocatalytic succinimide derivative synthesis from reaction of 1,6-enynes aryl sulfonyl bromide at room temperature under air ambient conditions. This method features mild conditions, broad substrate scope, high yields, excellent configurational selectivity. addition, all atoms substrates involved in converge product structures, showing a atomic economy. Moreover, most important characteristic this study that no photocatalyst additives are used, while key factor triggers visible light, indicating has practical value.

Язык: Английский

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