Cu/Picolinamides-Catalyzed Coupling of (Hetero)aryl Halides with Secondary Phosphine Oxides and Phosphite†

被引：8
|
作者：
Fang, Chao [1 ]
Wei, Bangguo [1 ]
Ma, Dawei [2 ]
机构：
[1] Fudan Univ, Sch Pharm, Dept Nat Med, 826 Zhangheng Rd, Shanghai 201203, Peoples R China
[2] Univ Chinese Acad Sci, Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem,State Key Lab Bioorgan, 345 Lingling Lu, Shanghai 200032, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2021年 / 39卷 / 11期
基金：
中国国家自然科学基金;
关键词：
Synthetic methods; Cross-Coupling; Aryl halides; Copper; Aryl phosphine oxides; P BOND FORMATION; ARYLBORONIC ACIDS; ROOM-TEMPERATURE; ARYL HALIDES; CHLORIDES; ARYLATION; DIPHENYLPHOSPHINE; PHOSPHORYLATION; BROMIDES;
D O I：
10.1002/cjoc.202100354
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Main observation and conclusion Some 4-hydroxy-picolinic acid derived amides were revealed as more efficient ligands for Cu-catalyzed coupling of (hetero)aryl halides with secondary phosphine oxides and phosphites. Only 3-5 mol% CuI and ligands were required to ensure coupling with a number of (hetero)aryl bromides and iodides to complete at 120 C-o in 10-20 h.
引用
收藏
页码：2957 / 2961
页数：5
相关论文
共 50 条
  • [1] Palladium-Catalyzed C-P Cross-Coupling between (Het)aryl Halides and Secondary Phosphine Oxides
    Zakirova, Gladis G.
    Mladentsev, Dmitrii Yu.
    Borisova, Nataliya E.
    SYNTHESIS-STUTTGART, 2019, 51 (11): : 2379 - 2386
  • [2] A Class of Amide Ligands Enable Cu-Catalyzed Coupling of (Hetero)aryl Halides with Sulfinic Acid Salts under Mild Conditions
    Zhao, Jinlong
    Niu, Songtao
    Jiang, Xi
    Jiang, Yongwen
    Zhang, Xiaojing
    Sun, Tiemin
    Ma, Dawei
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (12): : 6589 - 6598
  • [3] Cu2O Nanocube-Catalyzed Cross-Coupling of Aryl Halides with Phenols via Ullmann Coupling
    Kim, Jee Young
    Park, Ji Chan
    Kim, Aram
    Kim, A. Young
    Lee, Hyun Ju
    Song, Hyunjoon
    Park, Kang Hyun
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2009, (28) : 4219 - 4223
  • [4] Cu(II)-Catalyzed C-N Coupling of (Hetero)aryl Halides and N-Nucleophiles Promoted by α-Benzoin Oxime
    Yuan, Chunling
    Zhang, Lei
    Zhao, Yingdai
    MOLECULES, 2019, 24 (22):
  • [5] Copper-Catalyzed Hiyama Coupling of (Hetero)aryltriethoxysilanes with (Hetero)aryl Iodides
    Gurung, Santosh K.
    Thapa, Surendra
    Vangala, Adarsh S.
    Giri, Ramesh
    ORGANIC LETTERS, 2013, 15 (20) : 5378 - 5381
  • [6] Cu-Catalyzed Coupling Reactions of Sulfonamides with (Hetero)Aryl Chlorides/Bromides
    Li, Qiaoli
    Xu, Lanting
    Ma, Dawei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (43)
  • [7] Cobalt-Catalyzed Cross-Coupling of Functionalized Alkylzinc Reagents with (Hetero)Aryl Halides
    Lutter, Ferdinand H.
    Grokenberger, Lucie
    Spiess, Philipp
    Hammann, Jeffrey M.
    Karaghiosoff, Konstantin
    Knochel, Paul
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (14) : 5546 - 5550
  • [8] Copper-Catalyzed C-P Cross-Coupling of (Cyclo)alkenyl/Aryl Bromides and Secondary Phosphine Oxides with in situ Halogen Exchange
    Woznicki, Pawel
    Stankevic, Marek
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (24) : 3484 - 3491
  • [9] Ni-Catalyzed Cyanation of (Hetero)aryl Halides with Acetonitrile as Cyano Source
    Ahmad, Muhammad Siddique
    Zeng, Bing
    Qasim, Ruqiya
    Zheng, Dehui
    Zhang, Qing
    Jin, Yi
    Wang, Qifeng
    Meguellati, Kamel
    ACS CATALYSIS, 2024, 14 (04) : 2350 - 2357
  • [10] Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions
    Xia, Shanghua
    Gan, Lu
    Wang, Kaihang
    Li, Zheng
    Ma, Dawei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (41) : 13493 - 13496
12345