Well-Defined Air-Stable Palladium HASPO Complexes for Efficient Kumada-Corriu Cross-Couplings of (Hetero)Aryl or Alkenyl Tosylates

被引：71
作者：
Ackermann, Lutz [1 ]
Kapdi, Anant R. [1 ]
Fenner, Sabine [1 ]
Kornhaass, Christoph [1 ]
Schulzke, Carola [2 ]
机构：
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
[2] Trinity Coll Dublin, Sch Chem, Dublin 2, Ireland
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 10期
关键词：
catalysis; cross-coupling; ligand; palladium; tosylate; H BOND ACTIVATION; CATALYZED DIRECT ARYLATIONS; C-H; PHOSPHINOUS ACID; SUZUKI-MIYAURA; ARYL CHLORIDES; GRIGNARD-REAGENTS; HALOGENATED NITROGEN; INDOLE SYNTHESES; CARBON-OXYGEN;
D O I：
10.1002/chem.201002386
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Palladium complexes of representative heteroatom-substituted secondary phosphine oxide (HASPO) pre-ligands were synthesized and fully characterized, including X-ray crystal structure analysis. Importantly, these well-defined complexes served as highly efficient catalysts for Kumada-Corriu cross-coupling reactions of aryl, alkenyl, and even heteroaryl tosylates. Particularly, an air-stable catalyst derived from inexpensive PinP(O)H displayed a remarkably high catalytic efficacy, which resulted in cross-couplings at low catalyst loadings under exceedingly mild reaction conditions with ample scope.
引用
收藏
页码：2965 / 2971
页数：7
相关论文
共 108 条
  • [1] Steric Control in the Synthesis of Phosphinous Acid-Coordinated Mono- and Binuclear Platinum(II) Complexes
    Achard, Thierry
    Giordano, Laurent
    Tenaglia, Alphonse
    Gimbert, Yves
    Buono, Gerard
    [J]. ORGANOMETALLICS, 2010, 29 (17) : 3936 - 3950
  • [2] Catalytic arylation reactions by C-H bond activation with aryl tosylates
    Ackermann, L
    Althammer, A
    Born, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) : 2619 - 2622
  • [3] Air-stable phosphine oxides as preligands for catalytic activation reactions of C-Cl, C-F, and C-H bonds
    Ackermann, L
    Born, R
    Spatz, JH
    Althammer, A
    Gschrei, CJ
    [J]. PURE AND APPLIED CHEMISTRY, 2006, 78 (02) : 209 - 214
  • [4] Cross-coupling reactions of aryl and vinyl chlorides catalyzed by a palladium complex derived from an air-stable H-phosphonate
    Ackermann, L
    Gschrei, CJ
    Althammer, A
    Riederer, M
    [J]. CHEMICAL COMMUNICATIONS, 2006, (13) : 1419 - 1421
  • [5] Efficient aryl-(hetero)aryl coupling by activation of C-Cl and C-F bonds using nickel complexes of air-stable phosphine oxides
    Ackermann, L
    Born, R
    Spatz, JH
    Meyer, D
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (44) : 7216 - 7219
  • [6] Modular diamino- and dioxophosphine oxides and chlorides as ligands for transition-metal-catalyzed C-C and C-N couplings with aryl chlorides
    Ackermann, L
    Born, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) : 2444 - 2447
  • [7] General and efficient indole syntheses based on catalytic amination reactions
    Ackermann, L
    [J]. ORGANIC LETTERS, 2005, 7 (03) : 439 - 442
  • [8] Ackermann L., 2007, ANGEW CHEM, V119, P6482
  • [9] Ackermann L., 2005, Angew. Chem, V117, P2497
  • [10] Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
12345678910