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Synthesis 2021; 53(17): 3094-3100
DOI: 10.1055/a-1467-2432
special topic
Bond Activation – in Honor of Prof. Shinji Murai

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
,
Xing-Zhong Shu  ∗
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
› Author AffiliationsWe thank the National Natural Science Foundation of China for their financial support (21772072, 22071084).
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Abstract

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.

Key words

homocoupling - nickel - dibenzyls - alcohols - synthetic methodology

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1467-2432.
  • Supporting Information


Publication History

Received: 05 March 2021

Accepted after revision: 25 March 2021

Accepted Manuscript online:
25 March 2021

Article published online:
14 April 2021

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