Journal of Shanghai University(Natural Science Edition) ›› 2014, Vol. 20 ›› Issue (2): 221-227.doi: 10.3969/j.issn.1007-2861.2013.07.006

• Mathematics.Physics and Chemistry • Previous Articles     Next Articles

Optimization of Ligands in Nickel-Catalyzed Cross-Coupling of Alkyl Halides

XU Hai-liang1, ZHANG Yu-wei2, WANG Shu-lin1, LIANG Shuo1, TONG Wei-qi1   

  1. 1. College of Sciences, Shanghai University, Shanghai 200444, China;
    2. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China
  • Online:2014-04-26 Published:2014-04-26

Abstract: Construction of C(sp3)—C(sp3) bonds through direct nickel-catalyzed reductive cross-coupling of two structurally similar alkyl halides remains a challenge in organic synthesis. In the previous studies, under catalytic Ni(cod)2 in the presence of stoichiometric amount of Zn as reductant, two different alkyl halides can efficiently undergo coupling to give desired alkyl-alkyl products. However, one of the reactants has to be largely excessive. In order to improve coupling efficiency, this reaction by using 1 mol of (4-CI)-H-Pybox and 2 mol of Ni(cod)2 as model reactants was optimized. After screening a variety of tridentate and bidentate ligands, it was determined that the ligand remained optimal. However, bidentate ligand also gave moderate results in the presence of pyridine. This result may become important in future optimization.

Key words: C(sp3)—C(sp3) bonds, nickel-catalyzed, reductive cross-coupling

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