Synthesis of Benzoselenophenes and Benzothiophenes via Electrochemical Oxidative Seleno(Thio)cyanation/Cyclization Tandem Reaction of Enamides

An efficient stepwise electrochemical oxidative seleno(thio)cyanation/cyclization tandem reaction of enamides with XCN salts (X=Se and S) was developed herein to access a diverse range of C3-functionalized benzoselenophenes and benzothiophenes. This protocol can facilitate direct dual C(sp2)-H activ...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 12; no. 12
Main Authors Cheng, Zhenfeng, Gu, Qingyun, Zeng, Xiaobao
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.12.2023
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SULFONATED BENZOTHIOPHENES
THIOBORATION
ANNULATION
2-ALKYNYLTHIOANISOLES
Enamides
ALKYNES
METAL-FREE SYNTHESIS
Cyclization
Benzothiophenes
RADICAL CYCLIZATION
RONGALITE
Benzoselenophenes
SELENOANISOLES
CARBOTHIOLATION
Electrochemical
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Summary:An efficient stepwise electrochemical oxidative seleno(thio)cyanation/cyclization tandem reaction of enamides with XCN salts (X=Se and S) was developed herein to access a diverse range of C3-functionalized benzoselenophenes and benzothiophenes. This protocol can facilitate direct dual C(sp2)-H activation, offering versatility and broad substrate compatibility under mild reaction conditions. A stepwise electrochemical seleno(thio)cyanation/radical cyclization tandem reaction of enamides with XCN salts (X=Se and S) was developed to access various benzoselenophenes and benzothiophenes via a direct dual C(sp2)-H activation process, obviating the need for pre-installed halide functional groups as reaction handles, as well as stoichiometric transition-metal catalysts and strong redox reagents.image
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202300461