Cu II /TEMPO-Catalyzed Enantioselective C(sp 3 )-H Alkynylation of Tertiary Cyclic Amines through Shono-Type Oxidation

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 f...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2020-08, Vol.59 (35), p.15254-15259
Main Authors: Gao, Pei-Sen, Weng, Xin-Jun, Wang, Zhen-Hua, Zheng, Chao, Sun, Bing, Chen, Zhi-Hao, You, Shu-Li, Mei, Tian-Sheng
Format: Article
Language:English
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Summary: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202005099