Asymmetric three-component olefin dicarbofunctionalization enabled by photoredox and copper dual catalysis

Peng-Zi Wang, Yuan Gao, Jun Chen, Xiao-Die Huan, Wen-Jing Xiao () and Jia-Rong Chen ()
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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
Jia-Rong Chen: Central China Normal University

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: 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).

Date: 2021
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DOI: 10.1038/s41467-021-22127-x

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