Lewis Base Catalyzed Selenofunctionalization of Alkynes with Acid-Controlled Divergent Chemoselectivity  

作　　者：Ling-Ling Chen Ren-Fei Cao Hua Ke Zhi-Min Chen 

机构地区：[1]School of Chemistry and Chemical Engineering,Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs,Shanghai Jiao Tong University,Shanghai,200240 China [2]Engineering Technology Research Center for Environmental Protection Materials,Pingxiang University,Pingxiang,Jiangxi,337055 China

出　　处：《Chinese Journal of Chemistry》2024年第14期1623-1629,共7页中国化学（英文版）

基　　金：the National Natural Science Foundation of China(Nos.22071149,21871178);the Natural Science Foundation of Shanghai(23ZR1428200);the Program for Professor of Special Appointment(Eastern Scholar)at Shanghai Institutions of Higher Learning for financial support.

摘　　要：Lewis base catalyzed and Brønsted acid controlled chemodivergent electrophilic selenofunctionalizations of alkynes were developed for the first time.Various selenium-containing tetrasubstituted alkenes were readily obtained in moderate to excellent yields with complete E/Z selectivities.As the substrates were 1-ethynyl naphthol derivatives,linear selenium-containing tetrasubstituted alkenes were produced via intermolecular oxygen nucleophilic attack in the absence of acid additive;in contrast,cyclic selenium-containing tetrasubstituted alkenes were generated through intramolecular carbon nucleophilic capture with the addition of Brønsted acid.

关 键 词：ALKYNES Electrophilic addition CHEMOSELECTIVITY Lewis base catalysis Selenofunctionalization 

分 类 号：O62[理学—有机化学]