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
  • [31] Palladium-catalyzed coupling of vinyl tosylates with arylsulfinate salts
    Reeves, Diana C.
    Rodriguez, Sonia
    Lee, Heewon
    Haddad, Nizar
    Krishnamurthy, Dhileep
    Senanayake, Chris H.
    TETRAHEDRON LETTERS, 2009, 50 (24) : 2870 - 2873
  • [32] Addressing Challenges in Palladium-Catalyzed Cross-Couplings of Aryl Mesylates: Monoarylation of Ketones and Primary Alkyl Amines
    Alsabeh, Pamela G.
    Stradiotto, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (28) : 7242 - 7246
  • [33] Palladium-Catalyzed α-Arylation of Aryl Nitromethanes
    VanGelder, Kelsey F.
    Kozlowski, Marisa C.
    ORGANIC LETTERS, 2015, 17 (23) : 5748 - 5751
  • [34] Palladium-catalyzed cyanation of aryl triflates
    Zhu, Yi-Zhong
    Cai, Chun
    SYNTHETIC COMMUNICATIONS, 2008, 38 (16) : 2753 - 2760
  • [35] Palladium-catalyzed amination of aryl triflates
    Wolfe, JP
    Buchwald, SL
    JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05): : 1264 - 1267
  • [36] Palladium-catalyzed amination of aryl iodides
    Wolfe, JP
    Buchwald, SL
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03): : 1133 - 1135
  • [37] Preparation of enamides via palladium-catalyzed amidation of enol tosylates
    Klapars, A
    Campos, KR
    Chen, CY
    Volante, RP
    ORGANIC LETTERS, 2005, 7 (06) : 1185 - 1188
  • [38] Palladium-Catalyzed Amination of Aryl Sulfoxides
    Yoshida, Yuto
    Otsuka, Shinya
    Nogi, Keisuke
    Yorimitsu, Hideki
    ORGANIC LETTERS, 2018, 20 (04) : 1134 - 1137
  • [39] Palladium-catalyzed cyanation of aryl perfluorooctylsulfonates
    Zhu, Yi-Zhong
    Cai, Chun
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2008, 61 (08) : 581 - 584
  • [40] Palladium-catalyzed amination of aryl nonaflates
    Anderson, KW
    Mendez-Perez, M
    Priego, J
    Buchwald, SL
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (25): : 9563 - 9573