Synthesis of Dibenzyls by Nickel-Catalyzed Homocoupling of Benzyl Alcohols

被引:15
|
作者
Pan, Feng-Feng [1 ,2 ]
Guo, Peng [1 ]
Huang, Xiaochuang [3 ]
Shu, Xing-Zhong [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem SKLAOC, 222 South Tianshui Rd, Lanzhou 730000, Peoples R China
[2] Tianshui Normal Univ, Coll Chem Engn & Technol, 60 South Xihe Rd, Tianshui 741001, Peoples R China
[3] Jiangsu Tasly Diyi Pharmaceut Co Ltd, 168 West Chaoyang Rd, Huaian 223003, Jiangsu, Peoples R China
来源
SYNTHESIS-STUTTGART | 2021年 / 53卷 / 17期
基金
中国国家自然科学基金;
关键词
homocoupling; nickel; dibenzyls; alcohols; synthetic methodology;
D O I
10.1055/a-1467-2432
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:3094 / 3100
页数:7
相关论文
共 50 条
  • [1] Nickel-catalyzed α-alkylation of ketones with benzyl alcohols
    Wu, Di
    Wang, Yubin
    Li, Min
    Shi, Lei
    Liu, Jichang
    Liu, Ning
    APPLIED ORGANOMETALLIC CHEMISTRY, 2022, 36 (02)
  • [2] Dual Photoredox/Nickel-Catalyzed Dehydrative Difluoroalkylation of Benzyl Alcohols for the Synthesis of Allylic gem-Difluorides
    Bai, Yuyang
    Cao, Liping
    Li, Siyuan
    Zhang, Guang'an
    Liu, Yingguo
    Zhao, Fengqian
    Wu, Junliang
    ORGANIC LETTERS, 2023, 25 (35) : 6511 - 6516
  • [3] Nickel-Catalyzed Synthesis of Pyrimidines via Dehydrogenative Functionalization of Alcohols
    Chakraborty, Gargi
    Sikari, Rina
    Mondal, Rakesh
    Mandal, Sutanuva
    Paul, Nanda D.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (03) : 431 - 436
  • [4] SYNTHESIS OF ALLENES BY NICKEL-CATALYZED GRIGNARD REACTIONS WITH SILYLPROPARGYL ALCOHOLS
    WENKERT, E
    LEFTIN, MH
    MICHELOTTI, EL
    JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07): : 1122 - 1124
  • [5] Nickel-Catalyzed Isomerization of Homoallylic Alcohols
    Youmans, Dustin D.
    Tran, Hai N.
    Stanley, Levi M.
    ORGANIC LETTERS, 2023, 25 (19) : 3559 - 3563
  • [6] SYNTHESIS OF BIS(TRIFLUOROMETHYL)-2,2'-BIPYRIDINES BY NICKEL-CATALYZED HOMOCOUPLING REACTIONS
    CHAN, KS
    TSE, AKS
    SYNTHETIC COMMUNICATIONS, 1993, 23 (14) : 1929 - 1934
  • [7] Nickel-Catalyzed Carbonylation of Cyclopropanol with Benzyl Bromide for Multisubstituted Cyclopentenone Synthesis
    Hou, Liting
    Huang, Wenyi
    Wu, Xianqing
    Qu, Jingping
    Chen, Yifeng
    ORGANIC LETTERS, 2022, 24 (14) : 2699 - 2704
  • [8] Nickel-Catalyzed Homocoupling of Aryl Ethers with Magnesium Anthracene Reductant
    Rawat, Vishal Kumar
    Higashida, Kosuke
    Sawamura, Masaya
    SYNTHESIS-STUTTGART, 2021, 53 (18): : 3397 - 3403
  • [9] Nickel-catalyzed electrochemical homocoupling of alkenyl halides: Rates and mechanisms
    Cannes, C
    Labbe, E
    Durandetti, M
    Devaud, M
    Nedelec, JY
    JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1996, 412 (1-2): : 85 - 93
  • [10] Synthesis of α-methylene-β-lactones by nickel-catalyzed hydrocarboxylation of propargyl alcohols
    Roso-Levi, G.
    Amer, I.
    Journal of Molecular Catalysis, A: Chemical, 1996, 106 (1-2):