Enol Phosphinates and Phosphonates: Practical Electrophiles for Cross-Coupling Strategies

被引:25
|
作者
Steel, Patrick G. [1 ]
Woods, Tom M. [1 ,2 ]
机构
[1] Univ Durham, Dept Chem, Sci Labs, Durham DH1 3LE, England
[2] Ecole Polytech Fed Lausanne, Swiss Fed Inst Technol, Chem Synth Lab, CH-1015 Lausanne, Switzerland
来源
SYNTHESIS-STUTTGART | 2009年 / 22期
基金
英国工程与自然科学研究理事会;
关键词
lactams; arylboronic acids; stannanes; Suzuki-Miyaura coupling; Stille coupling; resin-bound enol phosphinate; NITROGEN-CONTAINING HETEROCYCLES; HETEROARYL BORONIC ACIDS; VINYL PHOSPHATES; ARYL; EFFICIENT; REAGENTS; LACTAMS;
D O I
10.1055/s-0029-1217067
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enol phosphinates and phosphonates can be readily prepared from simple lactams in high yields and are both stable and storable. Both these substrates can be employed successfully in homogeneous Suzuki-Miyaura and Stille cross-couplings protocols. Additionally, the phosphonate group can be immobilised on a phenol-on-polystyrene resin and utilised in a simple diversity linker strategy in which the coupled product is cleaved from the resin under Suzuki-Miyaura cross-coupling conditions.
引用
收藏
页码:3897 / 3904
页数:8
相关论文
共 50 条
  • [21] Sonogashira Cross-Coupling of Aryltrimethylammonium Salts
    Chen, Qianwei
    Gao, Fengchen
    Tang, Huiling
    Yao, Miao
    Zhao, Qan
    Shi, Yanhui
    Dang, Yanfeng
    Cao, Changsheng
    ACS CATALYSIS, 2019, 9 (04) : 3730 - 3736
  • [22] Gold and Palladium Combined for Cross-Coupling
    Hashmi, A. Stephen K.
    Lothschuetz, Christian
    Doepp, Rene
    Rudolph, Matthias
    Ramamurthi, Tanuja D.
    Rominger, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (44) : 8243 - 8246
  • [23] The dawn of cross-coupling
    Ananikov, Valentine P.
    NATURE CATALYSIS, 2021, 4 (09) : 732 - 733
  • [24] Cross-Coupling Reactions
    Bolm, Carsten
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (12) : 5221 - 5223
  • [25] Advances on N-Arylation of Indoles by Cross-Coupling Reactions
    Xu, Hui
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2009, 6 (04) : 367 - 377
  • [26] Cross-Coupling Reactions
    Bolm, Carsten
    ORGANIC LETTERS, 2012, 14 (12) : 2925 - 2928
  • [27] Copper-Catalyzed Oxidative Cross-Coupling of H-Phosphonates and Amides to N-Acylphosphoramidates
    Jin, Xiongjie
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    ORGANIC LETTERS, 2013, 15 (02) : 418 - 421
  • [28] Integrated Pd-catalyzed cross-coupling strategies for furnishing α-carbolines
    Sera, Misayo
    Mizufune, Hideya
    Ueda, Tsuyoshi
    Mineno, Masahiro
    Zanka, Atsuhiko
    TETRAHEDRON, 2017, 73 (40) : 5946 - 5958
  • [29] Synthesis of Aryl and Arylmethyl Phosphonates by Cross-Coupling of Aryl or Arylmethyl Halides (X = I, Br and Cl) with Diisopropyl H-Phosphonate
    Xu, Kai
    Hu, Hao
    Yang, Fan
    Wu, Yangjie
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (02) : 319 - 325
  • [30] Expedient Synthesis of Terminal Vinylphosphonates by Palladium-Catalyzed C-C Cross-Coupling Reactions of (1-Halovinyl)phosphonates
    Fang, Yewen
    Zhang, Li
    Jin, Xiaoping
    Li, Jinjian
    Yuan, Meijuan
    Li, Ruifeng
    Gao, Haoqi
    Fang, Jianghua
    Liu, Yuyan
    SYNLETT, 2015, 26 (07) : 980 - 984