Palladium-Catalyzed Phosphorylation of Aryl Mesylates and Tosylates

被引:98
|
作者
Fu, Wai Chung
So, Chau Ming
Kwong, Fuk Yee [1 ]
机构
[1] Hong Kong Polytech Univ, State Key Lab Chirosci, Kowloon, Hong Kong, Peoples R China
关键词
CROSS-COUPLING REACTIONS; P BOND FORMATION; ARYLBORONIC ACIDS; ALPHA-ARYLATION; INHIBITORS; PHOSPHINE; AMINATION; DIPHENYLPHOSPHINE; COMPLEXES; CHLORIDES;
D O I
10.1021/acs.orglett.5b03104
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first general palladium catalyst for the phosphorylation of aryl mesylates and tosylates is reported. The newly developed system exhibits excellent functional group compatibility. For instance, free amino, keto, ester, and amido groups, as well as heterocycles, remain intact during the course of reaction. The mesylated derivatives of biologically active compounds such as 17 beta-estradiol and 6-hydroxyflavone are also shown to be applicable substrates. A one-pot phosphorylation-amination sequence is described for the facile synthesis of potential phannacophores.
引用
收藏
页码:5906 / 5909
页数:4
相关论文
共 50 条
  • [41] Palladium-Catalyzed Aminosulfonylation of Aryl Halides
    Nguyen, Bao
    Emmett, Edward J.
    Willis, Michael C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (46) : 16372 - 16373
  • [42] PALLADIUM-CATALYZED SYNTHESES OF ARYL POLYENES
    MITSUDO, T
    FISCHETTI, W
    HECK, RF
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09): : 1640 - 1646
  • [43] Palladium-catalyzed α-arylation of aryl nitromethanes
    VanGelder, Kelsey
    Kozlowski, Marisa
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [44] Preparation of furans by palladium-catalyzed reaction of acylchromates and propargylic tosylates
    Nakamura, M
    Yamane, M
    Sakurai, H
    Narasaka, K
    HETEROCYCLES, 2003, 59 (01) : 333 - 345
  • [45] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides
    Cho, Eun Jin
    Senecal, Todd D.
    Kinzel, Tom
    Zhang, Yong
    Watson, Donald A.
    Buchwald, Stephen L.
    SCIENCE, 2010, 328 (5986) : 1679 - 1681
  • [46] Palladium-catalyzed amination of aryl chlorides
    Reddy, NP
    Tanaka, M
    TETRAHEDRON LETTERS, 1997, 38 (27) : 4807 - 4810
  • [47] Palladium-Catalyzed Aminocarbonylation of Aryl Halides
    Afsina, Cheriya Mukkolakkal Abdulla
    Philip, Rose Mary
    Saranya, Padinjare Veetil
    Anilkumar, Gopinathan
    CURRENT ORGANIC SYNTHESIS, 2023, 20 (03) : 308 - 331
  • [48] Palladium-catalyzed amination of aryl chlorides
    Reddy, N. P.
    Tanaka, M.
    Tetrahedron Letters, 38 (27):
  • [49] Enantioselective Intermolecular Heck and Reductive Heck Reactions of Aryl Triflates, Mesylates, and Tosylates Catalyzed by Nickel
    Huang, Xiaolei
    Teng, Shenghan
    Chi, Yonggui Robin
    Xu, Wenqiang
    Pu, Maoping
    Wu, Yun-Dong
    Zhou, Jianrong Steve
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (06) : 2828 - 2832
  • [50] Transition-Metal-Catalyzed Cross-Couplings of Aryl Tosylates or Mesylates with Organoindium Reagents
    Zhang, Liang
    Luo, Yong
    Wu, Jie
    SYNLETT, 2010, (12) : 1845 - 1848