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Cu II /TEMPO‐Catalyzed Enantioselective C(sp 3 )–H Alkynylation of Tertiary Cyclic Amines through Shono‐Type Oxidation
Author(s) -
Gao PeiSen,
Weng XinJun,
Wang ZhenHua,
Zheng Chao,
Sun Bing,
Chen ZhiHao,
You ShuLi,
Mei TianSheng
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202005099
Subject(s) - iminium , oxidizing agent , catalysis , chemistry , enantioselective synthesis , alkynylation , electrochemistry , copper , redox , tetrahydroisoquinoline , ligand (biochemistry) , oxidative coupling of methane , combinatorial chemistry , medicinal chemistry , organic chemistry , electrode , biochemistry , receptor
A novel strategy for asymmetric Shono‐type oxidative cross‐coupling has been developed by merging copper catalysis and electrochemistry, affording C1‐alkynylated tetrahydroisoquinolines with good to excellent enantioselectivity. The use of TEMPO as a co‐catalytic redox mediator is crucial not only for oxidizing a tetrahydroisoquinoline to an iminium ion species but also for decreasing the oxidation potential of the reaction. A novel bisoxazoline ligand is also reported.
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