Electrochemical Three-Component C–H Functionalization of Indoles with Sodium Bisulfite and Alcohols to Access Indole-Containing Sulfonate Esters

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 4, 2025

Herein, an efficient electrochemical three-component C-H functionalization of indoles with sodium bisulfite and alcohols is described, providing a sustainable convenient synthetic route for the construction structurally valuable indole-containing sulfonate esters in moderate to good yields. This protocol proceeds undivided cell without any metal catalysts or oxidants, features broad substrate scope, has excellent functional group tolerance. Preliminary mechanistic studies suggest that radical-radical pathway may be involved this reaction system.

Language: Английский

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Visible-Light-Promoted Oxidative Decarboxylative Acylation of Acenaphthenone-2-ylidene ketones with α-Keto Carboxylic Acids under Metal , Additonal Oxidant and Base-free condition

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134674 - 134674

Published: April 1, 2025

Language: Английский

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Electrochemical synthesis of allenyl silanes and allenyl boronic esters

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: May 17, 2025

Allenyl silanes and boronates are pivotal building blocks in organic synthesis. Nevertheless, their synthesis requires the manipulation of transition metal or highly reactive species. Hence, development more sustainable protocol is sought after. Here we show electrochemical allenyl boronic esters. This catalyst-free method proceeds under mild reaction conditions. The for shows an excellent efficiency a good functional group tolerance. isolated yields (28 examples, 45-95% yields) without use catalyst A similar developed boronates, which obtained low to moderate (13 5-55% yields). Finally, mechanism based on oxidative generation silyl boryl radicals suggested access these classes allenes.

Language: Английский

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

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 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.

Language: Английский

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Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 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.

Language: Английский

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