Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

Chemical Society Reviews, Год журнала: 2022, Номер 51(6), С. 2313 - 2382

Опубликована: Янв. 1, 2022

Visible-light photoredox catalysis has been regarded as an extremely powerful tool in organic chemistry, bringing the spotlight back to radical processes. The versatility of photocatalyzed reactions already demonstrated be effective providing alternative routes for cross-coupling well multicomponent reactions. photocatalyst allows generation high-energy intermediates through light irradiation rather than using highly reactive reagents or harsh reaction conditions. In a similar vein, electrochemistry experienced fruitful renaissance generating without need any catalyst. Such milder approaches pose basis toward higher selectivity and broader applicability. electrochemical reactions, species acts starter cascade events. This diverse reactivity use is usually not covered by classical methods. Owing availability cheaper more standardized photo- reactors, easily scalable flow-setups, it surprising that these two fields have become areas increased research interest. Keeping view, this review aimed at overview synthetic design MCRs involving and/or activation crucial step with particular focus on choice difunctionalized reagent.

Язык: Английский

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Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis

Journal of the American Chemical Society, Год журнала: 2021, Номер 143(13), С. 4903 - 4909

Опубликована: Март 24, 2021

N-Heterocyclic carbene (NHC) catalysis has emerged as a versatile tool in modern synthetic chemistry. Further increasing the complexity, several processes have been introduced that proceed via dual catalysis, where NHC organocatalyst operates concert with second catalytic moiety, significantly enlarging reaction scope. In biological transformations, multiple is generally used to access complex natural products. Guided by strategy, triple studied recently, three different modes are merged single process. this Communication, direct α-C–H acylation of various alkenes aroyl fluorides using NHC, sulfinate, and photoredox cooperative reported. The method allows preparation α-substituted vinyl ketones moderate high yields excellent functional group tolerance. Mechanistic studies reveal these cascades through sequential radical addition/coupling/elimination contrast known operate two sets interwoven cycles, process, all cycles interwoven.

Язык: Английский

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Recent Advances in Green Multi-Component Reactions for Heterocyclic Compound Construction

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

This review highlights the recent advances in multi-component reactions for synthesizing heterocyclic compounds via green approaches including photoredox catalysis, electrochemical activation, catalyst-free methods and use of water as sole solvent.

Язык: Английский

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Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

ChemistrySelect, Год журнала: 2020, Номер 5(42), С. 13103 - 13134

Опубликована: Ноя. 13, 2020

Abstract Sodium sulfinates, sulfinic acids, sulfonyl chlorides and hydrazides as readily available efficient sulfonylation reagents have been extensively explored in recent years. Sulfonyl radical can be generated from these via different methods, then the could react with various substrates pathways to afford corresponding products. In this review, we will summarize progress reaction using sodium three terms of reagents, classify reactions into four types: 1. Sulfonylation sulfinates. 2. acid. 3. chlorides. 4. hydrazides.

Язык: Английский

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Divergent reactivity of sulfinates with pyridinium salts based on one-versustwo-electron pathways

Chemical Science, Год журнала: 2021, Номер 12(19), С. 6629 - 6637

Опубликована: Янв. 1, 2021

Divergent reactions of sulfinates with pyridinium salts were developed by controlling the one-versustwo-electron reaction manifolds.

Язык: Английский

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Visible-light-induced surfactant-promoted sulfonylation of alkenes and alkynes with sulfonyl chloride by the formation of an EDA-complex with NaI in water at room temperature

Green Chemistry, Год журнала: 2021, Номер 23(15), С. 5467 - 5473

Опубликована: Янв. 1, 2021

We report an efficient visible-light-induced iodosulfonyl reaction of alkenes in water using EDA complex strategy at room temperature. The addition a cationic surfactant allows for the easy formation colored complexes water.

Язык: Английский

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Photoredox-Catalyzed and Copper(II) Salt-Assisted Radical Addition/Hydroxylation Reaction of Alkenes, Sulfur Ylides, and Water

ACS Catalysis, Год журнала: 2022, Номер 12(6), С. 3279 - 3285

Опубликована: Фев. 25, 2022

A visible light-driven photoredox-catalyzed and copper(II)-assisted three-component radical addition/hydroxylation reaction of alkenes, sulfur ylides, water is reported. This process shows broad substrate scope high functional group tolerance, with respect to both readily available ylides providing high-yielding practical access valuable γ-hydroxy carbonyl compounds. Key the success controlled generation α-carbonyl carbon radicals from via sulfonium salts by a visible-light-driven proton-coupled electron transfer (PCET) strategy in mixture 2,2,2-trifluoroethanol/CH2Cl2. Addition Cu(TFA)2·H2O helps accelerate radical-cation crossover improve efficiency. Mechanistic studies suggest that hydroxy moiety products stems water. study also builds up platform for further investigation into synthetic chemistry ylides.

Язык: Английский

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Visible-Light-Mediated Photoredox Carbon Radical Formation from Aqueous Sulfoxonium Ylides

Organic Letters, Год журнала: 2023, Номер 25(7), С. 1161 - 1165

Опубликована: Фев. 9, 2023

The visible-light-induced photoredox carbon radical formation from aqueous sulfoxonium ylides has been demonstrated for the first time. While direct reduction of by H2O efficiently generates corresponding hydrocarbon compounds, use additional alkenes as acceptors alters chemical reactivity to achieve alkene carboarylation N-arylacrylamides. Mechanistic studies reveal two different reaction pathways involved in resulting release dimethyl sulfone and form DMSO.

Язык: Английский

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Redox-neutral carbon–heteroatom bond formation under photoredox catalysis

Chemical Communications, Год журнала: 2023, Номер 59(46), С. 7004 - 7027

Опубликована: Янв. 1, 2023

This feature article presents all the recent reports on photoredox-catalyzed redox-neutral carbon–heteroatom coupling reactions up to March 2023.

Язык: Английский

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Photochemical Halogen-Bonding Promoted Synthesis of Vinyl Sulfones via Vinyl and Sulfonyl Radicals

Organic Letters, Год журнала: 2024, Номер 26(3), С. 636 - 641

Опубликована: Янв. 10, 2024

A photochemical halogen-bonding-assisted synthesis of vinyl sulfones via radical–radical cross-coupling bromines and sodium sulfinates is developed. This methodology offers a facile efficient approach to various with excellent functional group tolerance under metal-, photocatalyst-, base-, oxidant-free conditions. The reaction also applicable for the late-stage functionalization drug molecules hectogram scale. Moreover, instead sulfites being prepared, these reactions could be conducted using sulfonyl chlorides in one-pot method.

Язык: Английский

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