Author
Listed:
- Peng-Zi Wang
(Central China Normal University)
- Yuan Gao
(Central China Normal University)
- Jun Chen
(Central China Normal University)
- Xiao-Die Huan
(Central China Normal University)
- Wen-Jing Xiao
(Central China Normal University
Lanzhou University)
- Jia-Rong Chen
(Central China Normal University)
Abstract
The intermolecular three-component alkene vicinal dicarbofunctionalization (DCF) reaction allows installation of two different carbon fragments. Despite extensive investigation into its ionic chemistry, the enantioseletive radical-mediated versions of DCF reactions remain largely unexplored. Herein, we report an intermolecular, enantioselective three-component radical vicinal dicarbofunctionalization reaction of olefins enabled by merger of radical addition and cross-coupling using photoredox and copper dual catalysis. Key to the success of this protocol relies on chemoselective addition of acyl and cyanoalkyl radicals, generated in situ from the redox-active oxime esters by a photocatalytic N-centered iminyl radical-triggered C-C bond cleavage event, onto the alkenes to form new carbon radicals. Single electron metalation of such newly formed carbon radicals to TMSCN-derived L1Cu(II)(CN)2 complex leads to asymmetric cross-coupling. This three-component process proceeds under mild conditions, and tolerates a diverse range of functionalities and synthetic handles, leading to valuable optically active β–cyano ketones and alkyldinitriles, respectively, in a highly enantioselective manner (>60 examples, up to 97% ee).
Suggested Citation
Peng-Zi Wang & Yuan Gao & Jun Chen & Xiao-Die Huan & Wen-Jing Xiao & Jia-Rong Chen, 2021.
"Asymmetric three-component olefin dicarbofunctionalization enabled by photoredox and copper dual catalysis,"
Nature Communications, Nature, vol. 12(1), pages 1-10, December.
Handle:
RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-22127-x
DOI: 10.1038/s41467-021-22127-x
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