Electrochemical Sulfonylation of Alkynes with Sulfonyl Hydrazides: A Metal‐ and Oxidant‐Free Protocol for the Synthesis of Alkynyl Sulfones

Herein, an electrochemical oxidative cross‐coupling reaction between terminal alkynes and sulfonylhydrazides has been developed. Tetrabutylammonium iodide is used as the electrolyte and redox medium. The significant advantages of this method are high atom efficiency, functional group tolerance, and...

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Published inAdvanced synthesis & catalysis Vol. 362; no. 11; pp. 2160 - 2167
Main Authors Mo, Zu‐Yu, Zhang, Yu‐Zhen, Huang, Guo‐Bao, Wang, Xin‐Yu, Pan, Ying‐Ming, Tang, Hai‐Tao
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 26.05.2020
Wiley Subscription Services, Inc
Subjects
Alkynes
Alkynyl sulfones
Apoptosis
Cell adhesion & migration
Chemistry
Chemistry, Applied
Chemistry, Organic
Cross coupling
Cross-coupling reaction
Electrochemical synthesis
Electrolytic cells
Functional groups
Hydrazides
Oxidizing agents
Physical Sciences
Science & Technology
Sulfones
Sulfonylhydrazine
Terminal alkyne
Transition metals
Terminal alkyne
REAGENTS
STRATEGY
TERMINAL ALKYNES
ACETYLENIC SULFONES
DIARYLSULFONES
Alkynyl sulfones
DIFUNCTIONALIZATION
Sulfonylhydrazine
Cross-coupling reaction
ALKOXYSULFONYLATION
BONDS
INHIBITORS
Electrochemical synthesis
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Summary:Herein, an electrochemical oxidative cross‐coupling reaction between terminal alkynes and sulfonylhydrazides has been developed. Tetrabutylammonium iodide is used as the electrolyte and redox medium. The significant advantages of this method are high atom efficiency, functional group tolerance, and transition metal‐ and oxidant‐free conditions. Most of the compounds exhibit good inhibitory activity on tumor cell lines, and one of the compounds can inhibit cell migration and induce apoptosis in HeLa cells.
Bibliography:These authors contributed equally to this work
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901607