Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (11): 4208-4239.DOI: 10.6023/cjoc202106021 Previous Articles     Next Articles



吴良a, 魏瀚林a, 陈建中b,*(), 张万斌a,b,*()   

  1. a 上海交通大学药学院 变革性分子前沿科学中心 上海市手性药物分子工程重点实验室 上海 200240
    b 上海交通大学化学化工学院 上海 200240
  • 收稿日期:2021-06-10 修回日期:2021-06-22 发布日期:2021-07-19
  • 通讯作者: 陈建中, 张万斌
  • 基金资助:
    上海市“超级博士后”激励计划(2020272); 国家自然科学基金(21620102003); 国家自然科学基金(21772119); 国家自然科学基金(21831005)

Development of Nickel-Catalyzed Cross-Coupling of Alcohol Derivatives to Construct Carbon-Carbon Bonds

Liang Wua, Hanlin Weia, Jianzhong Chenb(), Wanbin Zhanga,b()   

  1. a Shanghai Key Laboratory for Molecular Engineering and Chiral Drugs, Frontiers Science Center for Transformative Molecules, School of Pharmacy, Shanghai Jiao Tong University, Shanghai 200240
    b School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
  • Received:2021-06-10 Revised:2021-06-22 Published:2021-07-19
  • Contact: Jianzhong Chen, Wanbin Zhang
  • Supported by:
    Shanghai Post-Doctoral Excellence Program(2020272); National Natural Science Foundation of China(21620102003); National Natural Science Foundation of China(21772119); National Natural Science Foundation of China(21831005)

Transition metal-catalyzed cross-coupling reactions for building carbon-carbon bonds have received extensive attention due to their high efficiency and selectivity. In recent years, electrophiles which containing C(sp3)—O bonds have been used to replace organic halides in cross-coupling reactions for the construction of C(sp3)—C bonds, due to their advantages of commercial availability or facile synthesis, high reaction selectivity, and environmental friendliness. Among those reported highly efficient catalysts, nickel catalysts have been gradually applied to such reactions and achieved remarkable advances due to their earth-abundant, cheap, unique catalytic activities and selectivity. Because of the small radius of the nickel atom, C(sp3)—Ni can inhibit and/or manipulate β-H elimination reactions, which reduces the formation of by-products. Nickel has several variable valence states and can flexibly participate in redox-neutral coupling reactions and reductive cross-coupling reactions. The latest research progress in nickel-catalyzed coupling reactions employing alcohol derivatives as electrophiles is reviewed. It is separated into four sections including nickel-catalyzed cross-coupling reactions involving methanol or primary alcohol derivatives, nickel-catalyzed cross-coupling reactions involving secondary alcohol derivatives, nickel-catalyzed cross-coupling reactions involving acetal and N,O-acetal derivatives, and nickel-catalyzed cross-coupling reactions involving tertiary alcohol derivatives.

Key words: Ni catalyst, alcohol derivatives, cross-coupling reactions, stereospecific synthesis, asymmetric catalysis