Ni-Catalyzed Decarboxylative Cross-Coupling of Potassium Polyfluorobenzoates with Unactivated Phenol and Phenylmethanol Derivatives

被引:18
|
作者
Chen, Quan [1 ]
Wu, Aizhen [1 ]
Qin, Shengxiang [1 ]
Zeng, Meiqi [1 ]
Le, Zhiping [1 ]
Yan, Zhaohua [1 ]
Zhang, Hua [1 ]
机构
[1] Nanchang Univ, Coll Chem, 999 Xuefu Ave, Nanchang 330031, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
decarboxylative cross-coupling; C-O bond functionalization; nickel-catalyzed; phenol derivatives; polyfluorobiaryls; C-O BOND; AROMATIC CARBOXYLATE SALTS; H BONDS; NICKEL CATALYSIS; DIRECT ARYLATION; BIARYL SYNTHESIS; ARYL HALIDES; ACTIVATION; CLEAVAGE; ACIDS;
D O I
10.1002/adsc.201800729
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A Ni-catalyzed decarboxylative cross-coupling of potassium polyfluorobenzoates with unactivated phenol and phenylmethanol derivatives is described. This novel transformation provides a practical and efficient protocol towards the synthesis of important polyfluorobiaryls and polyfluorinated diarylmethanes, and greatly enlarges the range of electrophiles utilized in decarboxylative coupling. Remarkably, preliminary mechanistic studies indicated the essential role of Zn(OAc)(2) might lie in the enhancement of decarboxylation step.
引用
收藏
页码:3239 / 3244
页数:6
相关论文
共 50 条
  • [41] Introducing Trifluoromethoxyarenes as Halide Surrogates in Mechanochemical Realizations of Ni-catalyzed Cross-coupling Reactions
    Mkrtchyan, Satenik
    Jakubczyk, Michal
    Budzak, Simon
    Benicka, Barbora
    Iaroshenko, Viktor O.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (06)
  • [42] Practical Ni-Catalyzed Cross-Coupling of Unsaturated Zinc Pivalates with Unsaturated Nonaflates and Triflates
    Hofmayer, Maximilian S.
    Lutter, Ferdinand H.
    Grokenberger, Lucie
    Hammann, Jeffrey M.
    Knochel, Paul
    ORGANIC LETTERS, 2019, 21 (01) : 36 - 39
  • [43] Ni-Catalyzed Desymmetric Radical Cross-Coupling Reaction to Access Axially Chiral Biaryls
    Zhu, Yue-Die
    Dai, Zhen-Yao
    Jiang, Min
    Wang, Pu-Sheng
    ACS CATALYSIS, 2024, 14 (18): : 13860 - 13866
  • [44] Ni-Catalyzed Cascade Cyclization-Kumada Alkyl-Alkyl Cross-Coupling
    Guisan-Ceinos, Manuel
    Soler-Yanes, Rita
    Collado-Sanz, Daniel
    Phapale, Vilas B.
    Bunuel, Elena
    Cardenas, Diego J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (26) : 8405 - 8410
  • [45] High Ortho Preference in Ni-Catalyzed Cross-Coupling of Halophenols with Alkyl Grignard Reagents
    Wang, Jia-Rui
    Manabe, Kei
    ORGANIC LETTERS, 2009, 11 (03) : 741 - 744
  • [46] Theoretical investigation of the mechanisms of the biphenyl formation in Ni-catalyzed reductive cross-coupling system
    Jiang, Feng
    Ren, Qinghua
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2014, 757 : 72 - 78
  • [47] Electrochemical Ni-Catalyzed Decarboxylative C(sp3)-N Cross-Electrophile Coupling
    Cai, Yue-Ming
    Liu, Xiao-Ting
    Xu, Lin-Lin
    Shang, Ming
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (12)
  • [48] NOVEL-APPROACH TO CROSS-COUPLING EXEMPLIFIED BY NI-CATALYZED REACTION OF ALKENYL-ZIRCONIUM DERIVATIVES WITH ARYL HALIDES
    NEGISHI, EI
    VANHORN, DE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1977, 173 (MAR20): : 123 - 123
  • [49] Pd(II)-Catalyzed Decarboxylative Cross-Coupling of Potassium Aryltrifluoroborates with α-Oxocarboxylic Acids at Room Temperature
    Li, Mingzong
    Wang, Cong
    Ge, Haibo
    ORGANIC LETTERS, 2011, 13 (08) : 2062 - 2064
  • [50] Site-Selective Ni-Catalyzed Reductive Coupling of α-Haloboranes with Unactivated Olefins
    Sun, Shang-Zheng
    Borjesson, Marino
    Martin-Montero, Raul
    Martin, Ruben
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (40) : 12765 - 12769