Visible-Light-Induced Redox-Neutral Difunctionalization of Alkenes and Alkynes

Chemical Communications, Год журнала: 2024, Номер 60(72), С. 9659 - 9691

Опубликована: Янв. 1, 2024

The twelve principles of green chemistry illuminate the pathway in direction sustainable and eco-friendly synthesis, marking a fundamental shift synthetic organic paradigms. In this realm, harnessing power visible light for difunctionalization various skeletons without employing any external oxidant or reductant, specifically termed as redox-neutral difunctionalization, has attracted tremendous interest from chemists due to its low cost, easy availability environmentally friendly nature contrast traditional metal-catalyzed difunctionalizations. This review presents an overview recent updates on visible-light-induced reactions with literature coverage up May 2024.

Язык: Английский

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Photochemical and Electrochemical Synthesis of Oxazoles and Isoxazoles: An Update

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(10), С. 2186 - 2208

Опубликована: Апрель 4, 2024

Abstract This review presents an outline of current advancements in the photochemical and electrochemical synthesis oxazoles isoxazoles. Oxazole isoxazole are important building blocks for a variety medicinally useful compounds. Therefore, these heterocycles via sustainable technologies is worth demanding. Photochemical two among few technologies. covers brief discussion on reaction parameters like catalysts, substrates scope, temperature, solvents, electrodes, electrolytes (in case process), light source process) individual reaction. Detailed mechanistic insight each also presented. Finally, summary, future direction toward development effective methods isoxazoles

Язык: Английский

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Visible-Light-Induced Energy-Transfer-Mediated Hydrofunctionalization and Difunctionalization of Unsaturated Compounds via Sigma-Bond Homolysis of Energy-Transfer Acceptors

ACS Catalysis, Год журнала: 2025, Номер 15(3), С. 1854 - 1941

Опубликована: Янв. 17, 2025

Over the past decade, visible-light-mediated energy-transfer (EnT) catalysis, particularly triplet–triplet (TTEnT) has emerged as a mild and environmentally friendly approach for diverse organic synthetic transformations. In contrast to photoredox which typically requires sacrificial electron donors or acceptors complete catalytic cycle, EnT photocatalysis generally proceeds with high atom economy while minimizing generation of wasteful byproducts. Furthermore, successful catalysis is contingent upon precise control redox potentials both photocatalysts substrates, strategies are primarily influenced by triplet energy compatibility between these entities. Considering growing importance photocatalysis, well hydrofunctionalization difunctionalization reactions in synthesis, this review systematically summarizes significant advancements EnT-enabled unsaturated compounds via sigma-bond homolysis over decade. Special emphasis placed on elucidating substrate scopes mechanistic scenarios. Additionally, discusses versatile applications methodologies addresses current challenges opportunities within evolving research field. This structured into six main categories based different types sigma-bonds undergoing homolysis. These include transformations mediated 1) N–O bond oxime esters other N,O-radical precursors; 2) N–S N-sulfonyl imines N,S-radical 3) chalcogen–chalcogen disulfides oxy/thio/selenosulfonates; 4) C–S tri/difluoromethylated sulfinates, acetylenic triflones, arylsulfonium salts; 5) C–X (X = halogen) halides; 6) acceptors. Through providing theoretical backgrounds along comprehensive overview currently employed acceptors, photosensitizers, contemporary EnT-induced compounds, aims serve an invaluable resource future innovations rapidly

Язык: Английский

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A radical Smiles rearrangement difunctionalization of activated alkenes via desulfonylation and insertion of sulfur dioxide relay strategy

Green Chemistry, Год журнала: 2024, Номер 26(11), С. 6774 - 6778

Опубликована: Янв. 1, 2024

A novel and attractive photochemical difunctionalization of N -tosyl acrylamide for constructing alkylsulfonylated oxindoles amides with excellent substrate adaptability via a radical Smiles rearrangement strategy is described.

Язык: Английский

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Electrochemical and photochemical reaction of isatins: a decade update

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(17), С. 3352 - 3375

Опубликована: Янв. 1, 2024

This review presents all the recent reports on electro- and photochemical reactions of isatins over last decade.

Язык: Английский

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Sustainable Synthesis through Catalyst‐Free Photoinduced Cascaded Bond Formation

Chemistry - An Asian Journal, Год журнала: 2024, Номер 19(14)

Опубликована: Май 8, 2024

The beginning of photochemical reactions revolutionized synthetic chemistry through sustainable practices. This review explores cutting-edge developments in leveraging light-induced processes for generating cascaded C-C and C-hetero bonds without catalysts. Significantly, catalyst-free photoinduced methodologies have garnered considerable attention, especially the creation varied heterocyclic frameworks drug design synthesis natural products. article delves into underlying mechanisms, addresses limitations, evaluates various methodologies, emphasizing potential photocatalyst transition metal-free to enhance sustainability. Divided two sections, it covers recent strides C-heteroatom multiple bond formation reactions.

Язык: Английский

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1,3-Difunctionalization of Alkenes by Cobaloxime Photocatalysis

Organic Letters, Год журнала: 2024, Номер 26(32), С. 6809 - 6813

Опубликована: Авг. 5, 2024

Represented herein is the first 1,3-difunctionalization of alkenes via photocatalysis. A single cobaloxime used to carry out two catalytic cycles in which not only as a photocatalyst initiate reaction but also metal catalyst for β-H elimination process. Electron-deficient alkenes, electron-rich and unactivated could be directly converted 1,3-bisphosphorylated products, even unsymmetric with H

Язык: Английский

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Visible Light-Induced Radical Cascade Functionalization of Quinoxalin-2(1H)-ones: Three-Component 1,2-Di(hetero)arylation Approach with Styrenes and Thianthrenium Salts

Organic Letters, Год журнала: 2024, Номер 26(41), С. 8821 - 8826

Опубликована: Окт. 9, 2024

The additive-free visible light-induced three-component 1,2-di(hetero)arylation of styrenes was developed using quinoxalin-2(1

Язык: Английский

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Photocatalyzed Azidofunctionalization of Alkenes via Radical‐Polar Crossover

Angewandte Chemie International Edition, Год журнала: 2025, Номер unknown

Опубликована: Янв. 2, 2025

The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical-polar crossover strategy. A broad range alkenes, including vinyl arenes, enamides, enol ethers, sulfides, dehydroamino esters, were regioselectively functionalized with an azide nucleophiles such as azoles, carboxylic acids, alcohols, phosphoric oximes, phenols. method led to more efficient synthesis 1,2-azidofunctionalized pharmaceutical intermediates when compared previous approaches, resulting in both reduction step count increase overall yield. scope limitations these transformations further investigated through standard unbiased selection 15 substrate combinations out 1,175,658 possible clustering technique.

Язык: Английский

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Photocatalyzed Azidofunctionalization of Alkenes via Radical‐Polar Crossover

Angewandte Chemie, Год журнала: 2025, Номер unknown

Опубликована: Янв. 2, 2025

Abstract The azidofunctionalization of alkenes under mild conditions using commercially available starting materials and easily accessible reagents is reported based on a radical‐polar crossover strategy. A broad range alkenes, including vinyl arenes, enamides, enol ethers, sulfides, dehydroamino esters, were regioselectively functionalized with an azide nucleophiles such as azoles, carboxylic acids, alcohols, phosphoric oximes, phenols. method led to more efficient synthesis 1,2‐azidofunctionalized pharmaceutical intermediates when compared previous approaches, resulting in both reduction step count increase overall yield. scope limitations these transformations further investigated through standard unbiased selection 15 substrate combinations out 1,175,658 possible clustering technique.

Язык: Английский

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