Electrochemically Oxidative C-H/N-H Cross-Coupling Reactions of Sulfoximines with Imidazopyridines.

J Org Chem

Biomass-Derived Functional Oligosaccharides Engineering Technology Research Center of Anhui Province, Engineering Research Center of Biomass Conversion and Pollution Prevention of Anhui Educational Institutions, School of Chemistry and Material Engineering, Fuyang Normal University, Fuyang, Anhui 23

Published: August 2025


Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

An electrochemically induced C-H/N-H cross-coupling of sulfoximines with imidazopyridines was achieved. This protocol provides a sustainable approach for the synthesis of C-3 sulfoximidoyl-functionalized imidazo[1,2-]pyridines in the absence of exogenous oxidants and metal catalysts.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.5c01245DOI Listing

Publication Analysis

Top Keywords

c-h/n-h cross-coupling
8
sulfoximines imidazopyridines
8
electrochemically oxidative
4
oxidative c-h/n-h
4
cross-coupling reactions
4
reactions sulfoximines
4
imidazopyridines electrochemically
4
electrochemically induced
4
induced c-h/n-h
4
cross-coupling sulfoximines
4

Similar Publications

Screening and dissecting electroorganic synthesis by mass spectrometry decoupling of electrode and homogeneous processes.

Nat Commun

August 2025

State Key Laboratory of Analytical Chemistry for Life Science, Chemistry and Biomedicine Innovation Center, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, PR China.

Rapid reaction screening and in-depth mechanistic exploration of electroorganic synthesis remain challenging due to low throughput of experimentation and high complexity of electrode and homogenous processes. Here, we report a decoupled electrochemical flow microreactor hyphenated mass spectrometry (namely DEC-FMR-MS) platform for high-throughput reaction screening and intermediate tracking of electrosynthesis. This platform combines in-capillary electrochemical transformation with operando MS interrogation, enabling rapid reactivity survey of a series of electrosynthetic reactions on nanomole scale.

View Article and Find Full Text PDF

Electrochemically Oxidative C-H/N-H Cross-Coupling Reactions of Sulfoximines with Imidazopyridines.

J Org Chem

August 2025

Biomass-Derived Functional Oligosaccharides Engineering Technology Research Center of Anhui Province, Engineering Research Center of Biomass Conversion and Pollution Prevention of Anhui Educational Institutions, School of Chemistry and Material Engineering, Fuyang Normal University, Fuyang, Anhui 23

An electrochemically induced C-H/N-H cross-coupling of sulfoximines with imidazopyridines was achieved. This protocol provides a sustainable approach for the synthesis of C-3 sulfoximidoyl-functionalized imidazo[1,2-]pyridines in the absence of exogenous oxidants and metal catalysts.

View Article and Find Full Text PDF

Reported herein is a photoredox/cobaloxime dual-catalytic approach to execute tandem dehydrogenative azolation and aromatization of tetrahydronaphthalene for rapid construction of -(β-naphthyl)azole architectures. This protocol highlights noble metal-free and external oxidants-free conditions, step- and atom-economy, and site-selectivity. A preliminary mechanistic study has uncovered that the transformation undergoes a -centered radical mediated C-H/N-H cross-coupling followed by dehydrogenative aromatization of saturated naphthyl surrogates under visible light irradiation, and DFT calculations elucidate the site-selectivity.

View Article and Find Full Text PDF

Selective Cleavage of C-O-4 Bond for Lignin Depolymerization via Paired-Electrolysis in an Undivided Cell.

Angew Chem Int Ed Engl

September 2024

Hubei Biomass-Resource Chemistry and Environmental Biotechnology Key Laboratory, School of Resource and Environmental Sciences, Wuhan University, 430079, Wuhan, P. R. China.

The cleavage of C-O bonds is one of the most promising strategies for lignin-to-chemicals conversion, which has attracted considerable attention in recent years. However, current catalytic system capable of selectively breaking C-O bonds in lignin often requires a precious metal catalyst and/or harsh conditions such as high-pressure H and elevated temperatures. Herein, we report a novel protocol of paired electrolysis to effectively cleave the C-O-4 bond of lignin model compounds and real lignin at room temperature and ambient pressure.

View Article and Find Full Text PDF

An electrochemical protocol for benzylic C(sp)-H aminopyridylation via direct C-H/N-H cross-coupling of alkylarenes with -aminopyridinium triflate has been developed. This method features excellent site-selectivity, broad substrate scope, redox reagent-free and facile scalability. The generated benzylaminopyridiniums can be readily converted to benzylamines via electroreductive N-N bond cleavage.

View Article and Find Full Text PDF