Synergistic use of photocatalysis and convergent paired electrolysis for nickel-catalyzed arylation of cyclic alcohols

Zhao-Ran Liu; Xiao-Yu Zhu; Jian-Feng Guo; Cong Ma; Zhiwei Zuo; Tian-Sheng Mei

doi:10.1016/j.scib.2024.04.031

Synergistic use of photocatalysis and convergent paired electrolysis for nickel-catalyzed arylation of cyclic alcohols

Sci Bull (Beijing). 2024 Apr 16:S2095-9273(24)00265-2. doi: 10.1016/j.scib.2024.04.031. Online ahead of print.

Authors

Zhao-Ran Liu¹, Xiao-Yu Zhu¹, Jian-Feng Guo¹, Cong Ma², Zhiwei Zuo³, Tian-Sheng Mei⁴

Affiliations

¹ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China.
² State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China. Electronic address: macong2016@sioc.ac.cn.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China. Electronic address: zuozhw@sioc.ac.cn.
⁴ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China. Electronic address: mei7900@sioc.ac.cn.

PMID: 38670850
DOI: 10.1016/j.scib.2024.04.031

Abstract

The merging of transition metal catalysis with electrochemistry has become a powerful tool for organic synthesis because catalysts can govern the reactivity and selectivity. However, coupling catalysts with alkyl radical species generated by anodic oxidation remains challenging because of electrode passivation, dimerization, and overoxidation. In this study, we developed convergent paired electrolysis for the coupling of nickel catalysts with alkyl radicals derived from photoinduced ligand-to-metal charge-transfer of cyclic alcohols and iron catalysts, providing a practical method for site-specific and remote arylation of ketones. The synergistic use of photocatalysis with convergent paired electrolysis can provide alternative avenues for metal-catalyzed radical coupling reactions.

Keywords: Electrophotocatalysis; Ni catalysis; Organic electrochemistry; Paired electrolysis; Remote arylation.