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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Three-Component Ring-Expansion Reaction of Indoles Leading to Synthesis of Pyrrolo[2,3-c]quinolines

Organic Letters, Journal Year: 2023, Volume and Issue: 25(37), P. 6886 - 6890

Published: Sept. 7, 2023

Herein, we have developed an atom- and step-economic three-component cascade reaction that enables a modular platform for the synthesis of pyrrolo[2,3-c]quinoline compounds through ring-expansion/cyclization by way novel N1–C2 cleavage indoles. The metal-free catalytic system exhibits broad functional group tolerance.

Language: Английский

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Synthesis of 3‐Arylazoindoles through Iron(III)‐Catalyzed C−H Azolation of Indoles and Arylhydrazines

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(9), P. 2123 - 2129

Published: March 6, 2024

Abstract A variety of functionalized 3‐arylazoindoles were prepared in good to excellent yields through an iron(III)‐catalyzed C−H azolation 2‐substituted indoles with arylhydrazines under mild reaction conditions. The underwent initial TBN‐mediated nitrosation, 1,5‐hydrogen migration, intramolecular condensation, and migration over four steps one pot. paracyclophane‐derived 3‐phenylazoindole could be 25% yield three some showed a different fluorescence emission wavelength existed obvious pH conditions response. present method highlights broad substrate scope easily available starting materials, wide range functional group compatibility, gram scalable preparations, high atom economy, avoidance unstable explosive reagents, simple purification operations by extraction, washing, recrystallization without flash column chromatography.

Language: Английский

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Selective Construction of C–S/S–N Bonds from N-Substituted O-Thiocarbamates and Indoles under Transition-Metal-Free Conditions

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4098 - 4112

Published: Feb. 29, 2024

A method for the selective construction of S–N/C(sp2)-S bonds using N-substituted O-thiocarbamates and indoles as substrates is reported. This protocol features good atom utilization, mild conditions, short reaction time, wide substrate scope, which can provide a convenient path functionalization indoles. In addition, could be scaled up on gram scale, showing potential application value in industry synthesis.

Language: Английский

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Recent advances in electrochemically enabled construction of indoles

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(65), P. 8516 - 8525

Published: Jan. 1, 2024

This review summarizes recent advances in the electrochemically enabled construction of indoles from non-indole-based precursors and their underlying mechanisms.

Language: Английский

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