Copper-Catalyzed Bis- or Trifunctionalization of Alkynyl Carboxylic Acids: An Efficient Route to Bis- and Tris-selenide Alkenes

A highly efficient copper-catalyzed protocol for the synthesis of bis- and tris-selenide alkenes from alkynyl carboxylic acids and diselenides has been developed. The reaction of alkynyl carboxylic acids and diselenides in the presence of CuI/Cs2CO3/toluene under white light LEDs only gave bis-selen...

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Published inAsian journal of organic chemistry Vol. 7; no. 5; pp. 892 - 896
Main Authors Chen, Jing, Su, Shi-Xia, Hu, Da-Chao, Cui, Fei-Hu, Xu, Yan-Li, Chen, Yan-Yan, Ma, Xian-Li, Pan, Ying-Ming, Liang, Ying
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.05.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
selenides
SE BOND ADDITION
decarboxylation
SOLVENT-FREE CONDITIONS
VINYL SELENIDES
EASY ACCESS
TERMINAL ALKYNES
alkenes
DECARBOXYLATIVE FUNCTIONALIZATION
DIPHENYL DISELENIDE
carboxylic acids
copper
STEREOSELECTIVE-SYNTHESIS
DERIVATIVES
DIARYL DISULFIDES
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Summary:A highly efficient copper-catalyzed protocol for the synthesis of bis- and tris-selenide alkenes from alkynyl carboxylic acids and diselenides has been developed. The reaction of alkynyl carboxylic acids and diselenides in the presence of CuI/Cs2CO3/toluene under white light LEDs only gave bis-selenide alkenes, whereas tris-selenide alkenes were obtained in the presence of a CuI/Cs2CO3/NMP system. This method provides a rapid access to bis-and tris-selenide alkenes derivatives.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201800086