Synthesis, characterization, and catalytic activity of N-heterocyclic carbene (NHC) palladacycle complexes

被引:278
作者
Viciu, MS [1 ]
Kelly, RA
Stevens, ED
Naud, F
Studer, M
Nolan, SP
机构
[1] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA
[2] Solvias AG, CH-4002 Basel, Switzerland
关键词
D O I
10.1021/ol034264c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
graphic Palladacycle dinners possessing bridging halides can be easily cleaved by using N-heterocyclic carbenes (NHCs) to generate novel monomeric complexes. The structure of one of these was determined by single-crystal diffraction study and consists of a square-planar coordination around the palladium center where the NHC ligand is trans to the amine of the palladacycle. The complex was found to be equally active in aryl amination and alpha-arylation of ketones even at very low catalyst loading (0.02 mol %). Primary and secondary alkyl/arylamines are equally active partners in coupling reactions.
引用
收藏
页码:1479 / 1482
页数:4
相关论文
共 38 条
  • [1] Mechanism of aryl chloride amination: Base-induced oxidative addition
    Alcazar-Roman, LM
    Hartwig, JF
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) : 12905 - 12906
  • [2] Oxime palladacycles:: Stable and efficient catalysts for carbon-carbon coupling reactions
    Alonso, DA
    Nájera, C
    Pacheco, MC
    [J]. ORGANIC LETTERS, 2000, 2 (13) : 1823 - 1826
  • [3] The role of ligand transformations on the performance of phosphite- and phosphinite-based palladium catalysts in the Suzuki reaction
    Bedford, RB
    Hazelwood, SL
    Limmert, ME
    Brown, JM
    Ramdeehul, S
    Cowley, AR
    Coles, SJ
    Hursthouse, MB
    [J]. ORGANOMETALLICS, 2003, 22 (07) : 1364 - 1371
  • [4] High-activity catalysts for Suzuki coupling and amination reactions with deactivated aryl chloride substrates: Importance of the palladium source
    Bedford, RB
    Cazin, CSJ
    Coles, SJ
    Gelbrich, T
    Horton, PN
    Hursthouse, MB
    Light, ME
    [J]. ORGANOMETALLICS, 2003, 22 (05) : 987 - 999
  • [5] The heck reaction as a sharpening stone of palladium catalysis
    Beletskaya, IP
    Cheprakov, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
  • [6] PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES
    ECHAVARREN, AM
    STILLE, JK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5478 - 5486
  • [7] Sulfur-containing palladacycles as catalyst precursors for the Heck reaction
    Gruber, AS
    Zim, D
    Ebeling, G
    Monteiro, AL
    Dupont, J
    [J]. ORGANIC LETTERS, 2000, 2 (09) : 1287 - 1290
  • [8] Improved functional group compatibility in the palladium-catalyzed synthesis of aryl amines
    Harris, MC
    Huang, XH
    Buchwald, SL
    [J]. ORGANIC LETTERS, 2002, 4 (17) : 2885 - 2888
  • [9] Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO
  • [10] 2-L