Electrochemical N(sp²)–H/C(sp³)–H cross-coupling reaction between sulfoximines and alkylarenes

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(10), P. 5824 - 5831

Published: Jan. 1, 2024

An electrochemical oxidation-induced amination of simple alkylarenes with sulfoximines as a nitrogen source and 5,6-dimethyl-1 H -benzo[ d ]imidazole catalyst was developed.

Language: Английский

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Electrochemical Benzylic C–H Functionalization with Isocyanides

Organic Letters, Journal Year: 2022, Volume and Issue: 24(11), P. 2125 - 2130

Published: March 14, 2022

We report the challenging direct carbamoylation or cyanation of benzylic C(sp3)–H bonds with an isocyanide via electrochemical process giving rise to structures that are encountered in several biologically relevant compounds and drugs. This transformation proceeds under mild conditions without need for any external oxidant avoids necessity start from a prefunctionalized substrate deployment cation pool method. The anodic oxidation position subsequent addition lead formation C–C bond nitrilium hydrolyzes yield α-aryl acetamide derivatives, whereas elimination t-butyl delivers acetonitrile derivatives.

Language: Английский

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The Application of Sulfonyl Hydrazides in Electrosynthesis: A Review of Recent Studies

ACS Omega, Journal Year: 2022, Volume and Issue: 7(44), P. 39531 - 39561

Published: Oct. 27, 2022

Sulfonyl hydrazides are viewed as alternatives to sulfinic acids and their salts or sulfonyl halides, which broadly used in organic synthesis work active pharmaceutical substances. Generally, considered good building blocks show powerful value a diverse range of reactions construct C–S bonds C–C bonds, even C–N sulfur, carbon, nitrogen sources, respectively. As profound synthetic tool, the electrosynthesis method was recently achieve efficient green applications hydrazides. Interestingly, many unique novel electrochemical syntheses using radical precursors have been developed, including cascade reactions, functionalization heterocycles, well continuous flow combining with since 2017. Accordingly, it is necessary specifically summarize recent developments only more deeply understand better design reactions. Herein, research 2017 reviewed detail based on chemical structures products reaction mechanisms.

Language: Английский

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Electrocatalytic synthesis: an environmentally benign alternative for radical-mediated aryl/alkenyl C(sp²)–C(sp³) cross-coupling reactions

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(24), P. 9373 - 9401

Published: Jan. 1, 2022

This review covers the recent progress in electrochemically enabled radical-mediated aryl/alkenyl C(sp 2 )–C(sp 3 ) cross-coupling reactions, including synthetic strategies, plausible mechanisms and further research outlook.

Language: Английский

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Electrochemical intramolecular N(sp²)–H/N(sp³)–H coupling for the synthesis of 1H-indazoles

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(10), P. 3982 - 3988

Published: Jan. 1, 2023

The electrochemical intramolecular cyclization of ketimines via N–H/N–H dehydrogenation coupling has been established for the construction 1 H -indazole scaffolds.

Language: Английский

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Cyclization of Azobenzenes Via Electrochemical Oxidation Induced Benzylic Radical Generation

Organic Letters, Journal Year: 2023, Volume and Issue: 25(32), P. 5978 - 5983

Published: Aug. 7, 2023

An electrochemical oxidation-induced cyclization of ortho-alkyl-substituted azobenzenes has been developed. The direct benzylic C-H functionalization with respect to could proceed in the absence any catalyst or external chemical oxidant afford a number 2H-indazole derivatives moderate good yields. This protocol enables reuse byproduct same 2H-indazoles, thus significantly reducing pollution discharge synthetic chemistry.

Language: Английский

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Electrochemical oxidation-induced benzylic C(sp³)–H functionalization towards the atom-economic synthesis of oxazole heterocycles

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(13), P. 5128 - 5133

Published: Jan. 1, 2023

A unique electrochemical four-component reaction of terminal alkynes, (thio)xanthenes, nitriles, and water has been established in the absence any catalyst or external oxidant.

Language: Английский

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Electrooxidation‐Induced C(sp³)–H/C(sp²)–H Radical‐Radical Cross‐Coupling between Xanthanes and Electron‐Rich Arenes

Chinese Journal of Chemistry, Journal Year: 2022, Volume and Issue: 40(12), P. 1422 - 1428

Published: March 15, 2022

Comprehensive Summary The arylation of C(sp 3 ) − H bonds has been a priority research topic in organic synthesis. Minsici reactions have the powerful methods for 2 formation. Despite its mature development, scopes arenes are usually suitable electron‐deficient heterocyclic compounds, rather than electron‐rich arenes. Herein, we report an electrooxidation‐induced alkylation with evolution under exogenous oxidant‐free conditions, avoiding utilization metal catalysts. This protocol is well performed various aniline derivatives and nitrogen‐containing compounds. We anticipate that this electro‐oxidative represents important expansion classic alkylation, thereby proving attractive strategy developments radical cross‐coupling chemistry.

Language: Английский

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Sustainable Approaches for the Synthesis of Functionalized Xanthene Derivatives with Anticancer Activities Using Modern Green Tools at Room Temperature: Less Energy and More Efficiency

Synlett, Journal Year: 2025, Volume and Issue: unknown

Published: April 30, 2025

Abstract Functionalized xanthenes occupy an important position in medicinal chemistry due to their wide range of pharmacological properties. The xanthene skeleton is present various bioactive natural products such as mulgravanols A and B, hermannol, (+)-myrtucommulone D, homapanicones blumeaxanthene II, acrotrione, etc. Important xanthene-based drugs, including propantheline bromide, methantheline, phloxine etc., are available on the market. Thus, much effort has been dedicated generating or modifying crucial O-heterocyclic compounds. Recently, development efficient processes for synthesis derivatives using modern techniques received significant attention overcome disadvantages traditional methodologies. Aligned with sixth principle green chemistry, which minimum energy needed perform synthetic methods at ambient temperature optimum productivity, this account focuses green, room-temperature strategies anticancer activities 1 Introduction 2 Synthesis Xanthene Derivatives through Green Strategies Room Temperature 3 Medicinal Perspectives Anticancer Agents 4 Conclusion 5 List Abbreviations

Language: Английский

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Electrooxidation-induced arylsulfonylation of xanthene derivatives with DABSO as an SO2 surrogate

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

An electrochemical redox C(sp3)-H arylsulfonylation of xanthenes has been developed using aryl diazonium tetrafluoroborates and DABSO as the arylsulfone source. This radical reaction proceeds via formation arylsulfonyl radicals from between DABSO, followed by a cross-coupling process. Notably, occurs in absence any catalyst or external oxidant, providing efficient sulfonylation with broad functional group compatibility.

Language: Английский

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