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Palladium/Copper Complexes Co‐Catalyzed Highly Enantioselective Ring Opening Reaction of Azabenzonorbornadienes with Terminal Alkynes
Author(s) -
Fan Baomin,
Li Sifeng,
Chen Hualei,
Lu Zhiwu,
Liu Shanshan,
Yang Qingjing,
Yu Lu,
Xu Jianbin,
Zhou Yongyun,
Wang Jun
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300748
Subject(s) - chemistry , palladium , enantioselective synthesis , trifluoromethanesulfonate , copper , catalysis , ring (chemistry) , substrate (aquarium) , medicinal chemistry , combinatorial chemistry , binap , metal , polymer chemistry , stereochemistry , organic chemistry , oceanography , geology
A chiral palladium/copper (Pd/Cu) co‐catalytic system which could enable asymmetric ring opening reaction of azabenzonorbornadienes with terminal alkynes is reported. This system comprises palladium(II) acetate [Pd(OAc) 2 ]/( R )‐xyl‐Binap and copper(I) triflate (CuOTf). A good substrate scope was found, with excellent enantioselective outcomes (up to >99.9 % ee ). A reaction mechanism involving two metal complexes is also proposed.