Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids

被引:98
作者
Chen, Hu [1 ,2 ]
Huang, Zhongbin [1 ,2 ]
Hu, Xiaoming [1 ,2 ]
Tang, Guo [1 ,2 ,4 ]
Xu, Pengxiang [1 ,2 ]
Zhao, Yufen [1 ,2 ,3 ]
Cheng, Chien-Hong [4 ]
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Fujian, Peoples R China
[3] Tsinghua Univ, Minist Educ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
[4] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
关键词
TEMPERATURE SUZUKI-MIYAURA; CARBON-CARBON BONDS; C-O ACTIVATION; BORONIC ACIDS; ALKENYL PHOSPHATES; ORGANOBORON COMPOUNDS; GRIGNARD-REAGENTS; ENOL ETHERS; ESTERS; ALKYNES;
D O I
10.1021/jo2000034
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Suzuki-Miyaura cross-coupling of aryl phosphates using Ni(PCy(3))(2)Cl(2) as an inexpensive, bench-stable catalyst is described. Broad substrate scope and high efficiency are demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. The poor reactivity of aryl phosphates relative to aryl halides is successfully employed to construct polyarenes by selective cross-coupling using Pd and Ni catalysts.
引用
收藏
页码:2338 / 2344
页数:7
相关论文
共 50 条
  • [1] Nickel-Catalyzed Decarbonylative Coupling of Aryl Esters and Arylboronic Acids
    LaBerge, Nicole A.
    Love, Jennifer A.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (25) : 5546 - 5553
  • [2] Nickel-catalyzed cross-coupling of carboxylic anhydrides with arylboronic acids
    Chen, Qiang
    Fan, Xin-Heng
    Zhang, Li-Peng
    Yang, Lian-Ming
    RSC ADVANCES, 2014, 4 (96) : 53885 - 53890
  • [3] Nickel-Catalyzed Cross-Coupling of Diarylborinic Acids with Aryl Chlorides
    Chen, Xiaofeng
    Ke, Haihua
    Zou, Gang
    ACS CATALYSIS, 2014, 4 (02): : 379 - 385
  • [4] Nickel-Catalyzed Cross-Coupling Reaction of Aryl Methyl Sulfides with Aryl Bromides
    Zhong, Chuntao
    Liu, Mengna
    Qiu, Xianchao
    Wei, Hao
    Cui, Benqiang
    Shi, Yanhui
    Cao, Changsheng
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (19) : 13418 - 13426
  • [5] Nickel-Catalyzed Cross-Coupling of Organolithium Reagents with (Hetero)Aryl Electrophiles
    Heijnen, Dorus
    Gualtierotti, Jean-Baptiste
    Hornillos, Valentin
    Feringa, Ben L.
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (12) : 3991 - 3995
  • [6] Nickel-Catalyzed Desulfitative Suzuki-Miyaura Cross-Coupling of N,N-Disulfonylmethylamines and Arylboronic Acids
    Chen, Liangshun
    Lang, Hongyue
    Fang, Lei
    Yu, Jianjun
    Wang, Limin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (29) : 6385 - 6389
  • [7] Nickel-Catalyzed Cross-Coupling of Aryl Fluorides and Organozinc Reagents
    Zhu, Feng
    Wang, Zhong-Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10) : 4285 - 4292
  • [8] Nickel-Catalyzed Cross-Coupling of gem-Difluoropropargyl Bromide with Aryl Boronic Acids
    Xiao Yulan
    Pan Qiang
    Zhang Xingang
    ACTA CHIMICA SINICA, 2015, 73 (05) : 383 - 387
  • [9] Nickel-Catalyzed Cross-Coupling of Ethyl Chlorofluoroacetate with Aryl Bromides
    Li, Han
    Sheng, Jie
    Wu, Bing-Bing
    Li, Yan
    Wang, Xi-Sheng
    CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (13) : 1741 - 1744
  • [10] Cross-Coupling of Aryl/Alkenyl Ethers with Aryl Grignard Reagents through Nickel-Catalyzed C-O Activation
    Xie, Lan-Gui
    Wang, Zhong-Xia
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (18) : 4972 - 4975