Recent advances on electrochemical generation of sulfonyl radical triggered cyclization of alkene/alkynes

Tetrahedron, Год журнала: 2025, Номер 173, С. 134467 - 134467

Опубликована: Янв. 12, 2025

Язык: Английский

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Electrochemical synthesis of γ-carbolinones via sulfonylation-triggered cyclization of indole-3-carboxamides

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 5, 2024

A novel electrochemical cyclization reaction of N -acryloyl-indole-3-carboxamides has been developed, which provides a new and efficient strategy for the synthesis γ-carbolinone derivatives.

Язык: Английский

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Organophotocatalytic Regioselective Silylation/Germylation and Cascade Cyclization of N-Alkenyl α-CF₃ Acrylamides: Access to Densely Functionalized 4-Pyrrolin-2-ones

Organic Letters, Год журнала: 2024, Номер 26(43), С. 9269 - 9275

Опубликована: Окт. 21, 2024

We report an organophotoredox-catalyzed silylation/germylation cascade cyclization of

Язык: Английский

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DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 2, 2024

Comprehensive Summary Herein, we report a rare example of three‐component net‐oxidative sulfonylation SO 2 surrogate with an oxidatively activated radical precursor under mild and metal‐ external‐oxidant‐free conditions. The mildness sustainability the reaction are enabled by photoelectrocatalysis, 3‐aza‐1,5‐dienes, organotrifluoroborates 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in atom‐economical manner broad substrate scope good functional‐group tolerance. protocol is amenable late‐stage diversification complex molecular architectures as well gram‐scale synthesis. Sunlight could be used light source, conducted all‐solar mode using commercially available photovoltaic panel generate electricity situ . Mechanistic studies reveal that generated (DABCO), which was generally innocent previous reactions, functions electron shuttle between photocatalytic cycle reactants.

Язык: Английский

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Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 18, 2024

We report an electrophotocatalytic process that enables the thiocyanation and sulfonylation/cyclization of alkenes. It is applicable to a wide range unactivated alkenes, using inexpensive photocatalyst 2,4,6-triphenylpyrylium tetrafluoroborate (TPPT) produce diverse array heterocycles containing sulfonyl thiocyano groups with good functional group tolerance. The protocol operates under mild, chemical oxidant- transition-metal-free, broad scope substrates. Preliminary mechanistic studies suggest reaction involves combination electrolysis reductive quenching photocatalytic cycle TPPT.

Язык: Английский

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Electrochemical domino sulfonylation/dearomative ipso‐annulation of 2‐alkynyl biaryls to access spiro(indenyl)cyclohexadienones

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 2, 2024

Abstract Herein, we present an efficient strategy for the synthesis of spiro(indenyl)cyclohexadienones through radical‐promoted reaction 2‐alkynyl biaryls with sodium sulfinates under electrochemical conditions. The involves sulfonylation and dearomative ipso‐ cyclisation in a domino fashion. This approach features use readily accessible precursors, wide functional group tolerance external oxidant‐free practicality method was also illustrated by scale‐up further diversification product.

Язык: Английский

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Sulfonylation/cyclization of alkynes with sulfonyl chlorides by copper catalysis

New Journal of Chemistry, Год журнала: 2024, Номер 48(47), С. 19746 - 19749

Опубликована: Янв. 1, 2024

A gentle and remarkably effective copper-catalyzed method for the cascade sulfonylation of alkynes using sulfonyl chlordies as direct sulfonylating reagents, is presented.

Язык: Английский

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Exploring nickel-catalyzed organochalcogen synthesis via cross-coupling of benzonitrile and alkyl chalcogenols with computational tools

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 30, 2024

The reaction mechanism of Ni(0)-catalyzed C–S cross-coupling between benzonitrile and propanethiol has been studied with DFT validated by microkinetic modeling. protocol is used to assess its potential usage for building C–Se C–Te bonds.

Язык: Английский

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