Solvent effects in palladium catalysed cross-coupling reactions

被引:223
|
作者
Sherwood, James [1 ]
Clark, James H. [1 ]
Fairlamb, Ian J. S. [1 ]
Slattery, John M. [1 ]
机构
[1] Univ York, Dept Chem, Heslington YO10 5DD, England
关键词
SUZUKI-MIYAURA REACTION; ARYL GRIGNARD-REAGENTS; CARBON BOND FORMATION; SOLVATOCHROMIC COMPARISON METHOD; TEMPERATURE IONIC LIQUIDS; DIPOLAR APROTIC-SOLVENT; BIO-BASED SOLVENTS; OXIDATIVE ADDITION; HECK REACTION; C-C;
D O I
10.1039/c9gc00617f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Palladium catalysed cross-couplings reactions have been a dominant method in synthetic chemistry for decades. Despite this, the role of the solvent is often taken for granted and poorly understood. Regulations affecting some the most frequently used solvents for cross-coupling reactions are accelerating current trends towards using new types of solvents. In this review, the fundamental interactions between solvent and catalyst are explained so that it may inform the rational selection of high performance and safe solvents. The popular cross-coupling methodologies are addressed (Suzuki, Stille, Kumada, Negishi, Hiyama, Heck, Sonogashira, and Buchwald-Hartwig reactions) and novel solvents introduced.
引用
收藏
页码:2164 / 2213
页数:50
相关论文
共 50 条
  • [1] Palladium catalysed cross-coupling reactions of silylamines
    Smith, CJ
    Early, TR
    Holmes, AB
    Shute, RE
    CHEMICAL COMMUNICATIONS, 2004, (17) : 1976 - 1977
  • [2] Allylboranes in palladium-catalysed cross-coupling reactions
    Kalinin, VN
    Denisov, FS
    Bubnov, YN
    MENDELEEV COMMUNICATIONS, 1996, (05) : 206 - 207
  • [3] Palladium-catalysed cross-coupling reactions on pyridazine moieties
    Nara, Susheel
    Martinez, Jean
    Wermuth, Camille-Georges
    Parrot, Isabelle
    SYNLETT, 2006, (19) : 3185 - 3204
  • [4] Palladium-Catalysed Cross-Coupling Reactions for the Synthesis of Chalcones
    Rullah, Kamal
    Aluwi, Mohd Fadhlizil Fasihi Mohd
    Yamin, Bohari M.
    Juan, Joon Ching
    Wai, Lam Kok
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (08) : 1174 - 1193
  • [5] Palladium-catalysed cross-coupling reactions in supercritical carbon dioxide
    Early, TR
    Gordon, RS
    Carroll, MA
    Holmes, AB
    Shute, RE
    McConvey, IF
    CHEMICAL COMMUNICATIONS, 2001, (19) : 1966 - 1967
  • [6] The role of the stabilizing/leaving group in palladium catalysed cross-coupling reactions
    Palio, Lorenzo
    Bru, Francis
    Ruggiero, Tommaso
    Bourda, Laurens
    Van Hecke, Kristof
    Cazin, Catherine
    Nolan, Steven P.
    DALTON TRANSACTIONS, 2024, 53 (44) : 18013 - 18020
  • [7] Palladium-catalysed cross-coupling and related reactions involving pyrroles
    Banwell, Martin G.
    Goodwin, Thomas E.
    Ng, Sarah
    Smith, Jason A.
    Wong, David J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (14) : 3043 - 3060
  • [8] Synthesis of monofunctionalised phthalocyanines using palladium catalysed cross-coupling reactions
    Ali, H
    vanLier, JE
    TETRAHEDRON LETTERS, 1997, 38 (07) : 1157 - 1160
  • [9] Synthesis of new aminoporphyrins via palladium-catalysed cross-coupling reactions
    Khan, MM
    Ali, H
    van Lier, JE
    TETRAHEDRON LETTERS, 2001, 42 (09) : 1615 - 1617
  • [10] Sonogashira cross-coupling reactions catalysed by copper-free palladium zeolites
    Djakovitch, L
    Rollet, P
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) : 1782 - 1792