Synthesis of Dibenzyls by Nickel-Catalyzed Homocoupling of Benzyl Alcohols
Feng-Feng Pan
a
State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. of China
b
College of Chemical Engineering and Technology, Tianshui Normal University, 60 South Xihe Road, Tianshui, 741001, P. R. of China
,
Peng Guo
a
State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. of China
,
Xiaochuang Huang
c
Jiangsu Tasly Diyi Pharmaceutical Co., Ltd., 168 West Chaoyang Road, Huai’An, Jiangsu, 223003, P. R. of China
a
State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering, Lanzhou University, 222 South Tianshui Road, Lanzhou, 730000, P. R. of China
› InstitutsangabenWe thank the National Natural Science Foundation of China for their financial support (21772072, 22071084).
Dibenzyls are essential building blocks that are widely used in organic synthesis, and they are typically prepared by the homocoupling of halides, organometallics, and ethers. Herein, we report an approach to this class of compounds using alcohols, which are more stable and readily available. The reaction proceeds via nickel-catalyzed and dimethyl oxalate assisted dynamic kinetic homocoupling of benzyl alcohols. Both primary and secondary alcohols are tolerated.
16 Metal-catalyzed coupling using strong basic nucleophiles:
Yu D.-G,
Wang X,
Zhu R.-Y,
Luo S,
Zhang X.-B,
Wang B.-Q,
Wang L,
Shi Z.-J.
J. Am. Chem. Soc. 2012; 134: 14638
19 It is possible that the oxalates undergo halide exchange to form benzyl halides, which can also react with nickel to form dimers. However, during the reactions, we have failed to detect any benzyl halides by GC-MS.
