Liu Zhao-Ran, Wang Ye, Ma Cong, Mei Tian-Sheng
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, China.
Precis Chem. 2025 Apr 10;3(7):357-364. doi: 10.1021/prechem.5c00015. eCollection 2025 Jul 28.
The synergistic integration of metal catalysis with electrochemistry has emerged as a powerful tool for organic synthesis. However, in nickel-catalyzed electrochemical cross-coupling reactions, mismatches between external conditions and reaction rates often lead to side reactions such as catalyst deactivation, homocoupling, and protonation. Addressing this issue through the development of strategies is highly desirable. Herein, we report the successful merging of photochemistry with electrochemistry to facilitate nickel-catalyzed C-O cross-coupling reactions, providing a practical method for the synthesis of alkyl aryl ethers. Preliminary mechanistic studies suggest that this photoelectrochemical strategy effectively enhances the efficiency of nickel-catalyzed C-O cross-coupling reactions compared to traditional electrochemical methods by regenerating the active Ni catalyst from the Ni species through photochemistry.
金属催化与电化学的协同整合已成为有机合成的有力工具。然而,在镍催化的电化学交叉偶联反应中,外部条件与反应速率之间的不匹配常常导致诸如催化剂失活、自偶联和质子化等副反应。通过开发策略来解决这一问题是非常必要的。在此,我们报道了光化学与电化学的成功结合,以促进镍催化的C-O交叉偶联反应,为烷基芳基醚的合成提供了一种实用方法。初步机理研究表明,与传统电化学方法相比,这种光电化学策略通过光化学从镍物种中再生活性镍催化剂,有效地提高了镍催化的C-O交叉偶联反应的效率。