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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Recent Advances in the Construction of Spiro Compounds via Radical Dearomatization

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 362(21), С. 4446 - 4461

Опубликована: Июль 15, 2020

Abstract The field in dearomatization of aromatic compounds for the construction spirocycle has been developed rapidly over last two decades and it provides alternative synthetic method without using extra stoichiometric amounts chemical oxidants or reductants. In addition, radical cascade reactions alkenes alkynes that produce multiple bonds one‐step are significant direct efficient building complex molecules. By combining these concepts, opens a new powerful avenue accessing These have well explored past decade. As result, we summarize recent eventful advances this growing area as review, which typical examples listed mechanism also discussed. magnified image

Язык: Английский

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Electrophilic Halospirocyclization of N-Benzylacrylamides to Access 4-Halomethyl-2-azaspiro[4.5]decanes

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(19), С. 13610 - 13621

Опубликована: Сен. 11, 2023

An electrophilic spirocyclization of N-benzylacrylamides with N-halosuccinimides (NXS) as the halogenating reagents has been developed. This reaction is carried out at room temperature under simple conditions without relying on metal reagents, photochemistry, or electrochemistry, providing a fast and efficient route to synthesize wide variety 4-halomethyl-2-azaspiro[4.5]decanes satisfactory yields. The approach further highlighted through gram-scale synthesis diverse transformations spiro products.

Язык: Английский

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Visible-light-promoted direct C–H/S–H cross-coupling of quinoxalin-2(1H)-ones with thiols leading to 3-sulfenylated quinoxalin-2(1H)-ones in air

Organic Chemistry Frontiers, Год журнала: 2019, Номер 6(24), С. 3950 - 3955

Опубликована: Янв. 1, 2019

A new and efficient visible-light-mediated strategy has been developed for the synthesis of 3-sulfenylated quinoxalin-2(1H)-ones via rhodamine B catalyzed C–H/S–H cross-coupling with thiols in air at room temperature.

Язык: Английский

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Visible-light-initiated malic acid-promoted cascade coupling/cyclization of aromatic amines and KSCN to 2-aminobenzothiazoles without photocatalyst

Chinese Chemical Letters, Год журнала: 2020, Номер 31(7), С. 1895 - 1898

Опубликована: Фев. 8, 2020

Язык: Английский

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Visible-light photoredox-catalyzed dual C–C bond cleavage: synthesis of 2-cyanoalkylsulfonylated 3,4-dihydronaphthalenes through the insertion of sulfur dioxide

Chemical Communications, Год журнала: 2020, Номер 56(20), С. 3011 - 3014

Опубликована: Янв. 1, 2020

An efficient novel visible-light photoredox-catalyzed dual carbon-carbon bond cleavage of methylenecyclopropanes and cycloketone oximes for the synthesis 2-cyanoalkylsulfonated 3,4-dihydronaphthalenes through insertion sulfur dioxide is established. This bonds involves a radical pathway goes sequence iminyl formation, cleavage, insertion, sulfonyl addition, another intramolecular cyclization.

Язык: Английский

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Recent Progress and Emerging Technologies towards a Sustainable Synthesis of Sulfones

ChemSusChem, Год журнала: 2021, Номер 14(22), С. 4878 - 4902

Опубликована: Сен. 3, 2021

Sulfones play a pivotal role in modern organic chemistry. They are highly versatile building blocks and find various applications as drugs, agrochemicals, or functional materials. Therefore, sustainable access to this class of molecules is great interest. Herein, the goal was provide summary on recent developments field sulfone synthesis. Advances existing limitations traditional approaches towards sulfones were reviewed selected examples. Furthermore, novel emerging technologies for more synthesis future directions discussed.

Язык: Английский

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Metal Free Sulfonylative Spirocyclization of Alkenyl and Alkynyl Amides via Insertion of Sulfur Dioxide

Advanced Synthesis & Catalysis, Год журнала: 2019, Номер 362(1), С. 224 - 229

Опубликована: Ноя. 13, 2019

Abstract Herein, we report an efficient synthesis of azaspiro[4,5]‐decanes and azaspiro[4,5]‐trienones by the radical cascade spirocyclization N‐ benzylacrylamides or N ‐arylpropiolamides respectively. These reactions proceed under metal free conditions involve in situ generation aryl sulfonyl radicals from DABSO diazonium salts. Furthermore, a catalyst visible light mediated protocol was developed for sulfonylative ‐aryl alkynamides using diaryliodonium The utility these protocols were justified excellent compatability wide range functional groups, good yields scalablity mild at room temperature. magnified image

Язык: Английский

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Heterogeneous Carbon Nitrides Photocatalysis Multicomponent Hydrosulfonylation of Alkynes To Access β-Keto Sulfones with the Insertion of Sulfur Dioxide in Aerobic Aqueous Medium

Organic Letters, Год журнала: 2020, Номер 22(2), С. 670 - 674

Опубликована: Янв. 7, 2020

Although hydrosulfonylation of alkynes is an ideal process to generate β-keto sulfones, such approach rarely implemented. Here we reported a facile and efficient graphitic carbon nitride (p-g-C3N4) photocatalyzed with the insertion sulfur dioxide in aerobic conditions. Controlled experiments ESR results indicated both superoxide radicals valence band holes played important role reaction. Further isotope confirmed oxygen atom products comes from H2O, while O2 plays reaction by quenching DABCO radical cation. The metal-free heterogeneous semiconductor fully recyclable at least 6 times without significant reducing activity. Furthermore, this could be carried out under solar light irradiation was applicable for large-scale conserved results.

Язык: Английский

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Photoinduced intramolecular carbosulfonylation of alkynes: access to sulfone-containing dibenzazepines from sulfur dioxide

Chemical Communications, Год журнала: 2021, Номер 57(23), С. 2883 - 2886

Опубликована: Янв. 1, 2021

A visible-light-driven three-component carbosulfonylation of terminal alkynes, DABCO (SO₂)₂ and aryldiazonium tetrafluoroborates is developed, leading to sulfone-containing dibenzazepines in moderate good yields under mild conditions.

Язык: Английский

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