Allylic substitution in water catalyzed by amphiphilic resin-supported palladium-phosphine complexes

被引:96
作者
Danjo, H
Tanaka, D
Hayashi, T [1 ]
Uozumi, Y
机构
[1] Kyoto Univ, Fac Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
[2] Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan
基金
日本学术振兴会;
关键词
D O I
10.1016/S0040-4020(99)00883-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New amphiphilic resin-supported triarylphosphines PEP (1) were designed and prepared on polyethylene glycol-polystyrene graft copolymer (PEG-PS). Palladium complexes of 1, Pd(PEP)(2) (4) and Pd(PEP) (5), catalyzed allylic alkylation of 3-acetoxy-1,3-diphenyl-1-propene (6) and cinnamyl acetate (7) with various nucleophiles including 1,3-dicarbonyl compounds, amino acids, sodium azide, and sodium sulfinate, to give quantitative yields of corresponding allylic substituted products in water. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:14341 / 14352
页数:12
相关论文
共 46 条
  • [1] NEW SYNTHETIC APPLICATIONS OF WATER-SOLUBLE ACETATE PD/TPPTS CATALYST GENERATED IN-SITU - EVIDENCE FOR A TRUE PD(0) SPECIES INTERMEDIATE
    AMATORE, C
    BLART, E
    GENET, JP
    JUTAND, A
    LEMAIREAUDOIRE, S
    SAVIGNAC, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21) : 6829 - 6839
  • [2] Anastas P.T., 1996, GREEN CHEM DESIGNING, DOI [10.1021/bk-1996-0626, DOI 10.1021/BK-1996-0626]
  • [3] [Anonymous], 1997, ORGANIC SYNTHESIS WA
  • [4] Bayer E., 1986, CHEM PEPTIDES PROTEI, V3, P3
  • [5] Water-soluble polymer-bound, recoverable palladium(0)-phosphine catalysts
    Bergbreiter, DE
    Liu, YS
    [J]. TETRAHEDRON LETTERS, 1997, 38 (45) : 7843 - 7846
  • [6] PALLADIUM(0)-CATALYZED SUBSTITUTION OF ALLYLIC SUBSTRATES IN AN AQUEOUS-ORGANIC MEDIUM
    BLART, E
    GENET, JP
    SAFI, M
    SAVIGNAC, M
    SINOU, D
    [J]. TETRAHEDRON, 1994, 50 (02) : 505 - 514
  • [7] PALLADIUM-CATALYZED ARYLATION OF STYRENE AND ACRYLIC-ACID IN WATER
    BUMAGIN, NA
    BYKOV, VV
    SUKHOMLINOVA, LI
    TOLSTAYA, TP
    BELETSKAYA, IP
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 486 (1-2) : 259 - 262
  • [8] BUNIN BA, 1998, COMBINATORIAL INDEX, P262
  • [9] Synthesis of benzofuran derivatives on solid support via SmI2-mediated radical cyclization
    Du, XH
    Armstrong, RW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) : 5678 - 5679
  • [10] Chemical library purification strategies based on principles of complementary molecular reactivity and molecular recognition
    Flynn, DL
    Crich, JZ
    Devraj, RV
    Hockerman, SL
    Parlow, JJ
    South, MS
    Woodard, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (21) : 4874 - 4881