Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane:: Synthesis, crystal structure and use in the Suzuki and Sonogashira reactions and the α-arylation of ketones

被引:114
作者
Adjabeng, G
Brenstrum, T
Frampton, CS
Robertson, AJ
Hillhouse, J
McNulty, J
Capretta, A
机构
[1] McMaster Univ, Dept Chem, Hamilton, ON L8S 4M1, Canada
[2] Bruker Nonius BV, NL-2612 HL Delft, Netherlands
[3] Cytec Canada Inc, Niagara Falls, ON L2E 6T4, Canada
关键词
D O I
10.1021/jo049474x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane were prepared and characterized with Pd[1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane](2).dba shown to be an effective catalyst for use in the Suzuki and Sonogashira reactions and the alpha-arylation of ketones. Couplings using this versatile complex proceeded in excellent yields under mild conditions.
引用
收藏
页码:5082 / 5086
页数:5
相关论文
共 18 条
  • [1] Novel class of tertiary phosphine ligands based on a phospha-adamantane framework and use in the Suzuki cross-coupling reactions of aryl halides under mild conditions
    Adjabeng, G
    Brenstrum, T
    Wilson, J
    Frampton, C
    Robertson, A
    Hillhouse, J
    McNulty, J
    Capretta, A
    [J]. ORGANIC LETTERS, 2003, 5 (06) : 953 - 955
  • [2] Böhm VPW, 2000, EUR J ORG CHEM, V2000, P3679, DOI 10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.CO
  • [3] 2-X
  • [4] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles
    Culkin, DA
    Hartwig, JF
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) : 234 - 245
  • [5] Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
  • [6] Pd(PhCN)2Cl2/P(t-Bu)3:: A versatile catalyst for sonogashira reactions of aryl bromides at room temperature
    Hundertmark, T
    Littke, AF
    Buchwald, SL
    Fu, GC
    [J]. ORGANIC LETTERS, 2000, 2 (12) : 1729 - 1731
  • [7] Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions
    Littke, AF
    Dai, CY
    Fu, GC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4020 - 4028
  • [8] Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO
  • [9] 2-U
  • [10] Littke AF, 1999, ANGEW CHEM INT EDIT, V38, P2411, DOI 10.1002/(SICI)1521-3773(19990816)38:16<2411::AID-ANIE2411>3.0.CO