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Electrochemical One-Step Synthesis of Alkyne Sulfonates and Sulfonamides: Building Blocks for Highly Substituted Alkenes and 1,3-Butadienes

Azizzade, Meysam; Breitschaft, Florian A.; Waldvogel, Siegfried R. 1; Opatz, Till
1 Institut für Biologische und Chemische Systeme (IBCS), Karlsruher Institut für Technologie (KIT)

Abstract (englisch):

Alkyne motifs have a central place in organic synthesis due to their versatility as building blocks for complex molecule construction. The development of efficient and sustainable strategies for the synthesis of functionalized alkynes remains an utmost challenge in modern organic chemistry. Herein, we report a novel and efficient electrochemical multicomponent reaction (eMCR) that enables the one-step synthesis of valuable alkyne sulfonates and sulfonamides using SO$_2$ stock solutions and electric current as a clean oxidant. The generated alkynyl sulfonates and sulfonamides serve as powerful synthetic intermediates, undergoing diverse downstream transformations, including regio- and stereoselective copper-catalyzed dimerizations, hydroarylations, and cyclizations, to access 1,3-dienes, highly substituted alkenes, and heterocycles. Moreover, this method enables late-stage functionalization of complex molecules and pharmaceuticals, demonstrating its significant potential for natural product synthesis, medicinal chemistry, and materials science. The study underscores the promise of electrochemical MCRs as sustainable and versatile tools in modern synthetic methodology.


Verlagsausgabe §
DOI: 10.5445/IR/1000189067
Veröffentlicht am 22.12.2025
Originalveröffentlichung
DOI: 10.1021/jacsau.5c00972
Scopus
Zitationen: 1
Dimensions
Zitationen: 1
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 24.11.2025
Sprache Englisch
Identifikator ISSN: 2691-3704
KITopen-ID: 1000189067
Erschienen in JACS Au
Verlag ACS Publications
Band 5
Heft 11
Seiten 5493 - 5503
Vorab online veröffentlicht am 23.10.2025
Schlagwörter alkynes, sulfonates, sulfur dioxide, electrochemistry, copper catalysis
Nachgewiesen in OpenAlex
Scopus
Dimensions
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