Secondary phosphine oxides: Versatile ligands in transition metal-catalyzed cross-coupling reactions

被引:176
|
作者
Shaikh, Tanveer Mahamadali [1 ]
Weng, Chia-Ming [1 ]
Hong, Fung-E [1 ]
机构
[1] Natl Chung Hsing Univ, Dept Chem, Taichung 40227, Taiwan
关键词
Secondary phosphine oxide (SPO); Cross-coupling; SPO in asymmetric reactions; Density functional theory (DFT); Palladium; CARBON-CARBON BOND; CHIROGENIC DIAMINOPHOSPHINE OXIDES; ASYMMETRIC ALLYLIC AMINATION; PREPARING AROMATIC KETONES; ARYL GRIGNARD-REAGENTS; HIGHLY-ACTIVE CATALYST; SUZUKI-MIYAURA TYPE; ACYL CHLORIDES; ACID-CHLORIDES; ARYLBORONIC ACIDS;
D O I
10.1016/j.ccr.2011.11.007
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This review describes the development in the use of secondary phosphine oxides ligands in transition-metal-catalyzed oxidative coupling reactions to the formation of C-C, C-N and C-S bonds. Also the developments in the recent literature are highlighted in the areas of cycloaddition, coupling of acyl halide with organometallic reagents, oxidations and other reactions. The secondary phosphine oxides are known to exist in the tautomeric forms and are configurationally stable; this property enables a variety of useful transformations for accessing optically active organophosphorus compounds which are useful in the formation of C-C bonds and asymmetric hydrogenation reactions. Finally, the mechanistic aspect employing DFT technique in these oxidative coupling reactions is described in this article. (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码:771 / 803
页数:33
相关论文
共 50 条
  • [1] Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Cross-coupling Reactions
    Shaughnessy, Kevin H.
    CURRENT ORGANIC CHEMISTRY, 2020, 24 (03) : 231 - 264
  • [2] Metal-Catalyzed Cross-Coupling Reactions of Aminopyridines
    Pires, Marina J. Dias
    Poeira, Diogo L.
    Marques, M. Manuel B.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (33) : 7197 - 7234
  • [3] Functionalization of indazoles by means of transition metal-catalyzed cross-coupling reactions
    El Kazzouli, Said
    Guillaumet, Gerald
    TETRAHEDRON, 2016, 72 (43) : 6711 - 6727
  • [4] Secondary Alkyl Halides in Transition-Metal-Catalyzed Cross-Coupling Reactions
    Rudolph, Alena
    Lautens, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (15) : 2656 - 2670
  • [5] Progress of transition metal-catalyzed cross-coupling mediated by PyBroP
    Chen, Guojun
    Du, Jianshi
    CHINESE SCIENCE BULLETIN, 2014, 59 (17): : 1942 - 1949
  • [6] Transition-Metal-Catalyzed Oxidative Cross-Coupling Reactions
    Liu, Chao
    Jin, Liqun
    Lei, Aiwen
    SYNLETT, 2010, (17) : 2527 - 2536
  • [7] Recent Advances in Transition Metal-Catalyzed Cross-Coupling Reactions Directly Promoted by Visible Light
    Li, Zhenlong
    Jin, Jian
    Huang, Shahua
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (03) : 563 - 574
  • [8] N-Tosylhydrazones: versatile reagents for metal-catalyzed and metal-free cross-coupling reactions
    Shao, Zhihui
    Zhang, Hongbin
    CHEMICAL SOCIETY REVIEWS, 2012, 41 (02) : 560 - 572
  • [9] Progress on the Transition Metal-catalyzed Cross-coupling Reaction of Thioesters
    Han Mingliang
    Xu Lihua
    ACTA CHIMICA SINICA, 2023, 81 (04) : 381 - 392
  • [10] Synthesis of functionalized alkenes by transition metal-catalyzed carbostannylations of alkynes and dienes followed by cross-coupling reactions
    Shirakawa, E
    Hiyama, T
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) : 114 - 121