Functionalization of sulfophthalocyanines in aqueous medium by palladium-catalyzed cross-coupling reactions

被引:19
作者
Ali, Hasrat [1 ]
St-Jean, Olivier [1 ]
Tremblay-Morin, Jean-Philip [1 ]
van Lier, Johan E. [1 ]
机构
[1] Univ Sherbrooke, Fac Med & Hlth Sci, Dept Med Nucl & Radiobiol, Sherbrooke, PQ J1H 5N4, Canada
基金
加拿大健康研究院;
关键词
phthalocyanines; palladium catallysis; green chemistry; PHOTODYNAMIC ACTIVITY; CATIONIC-PORPHYRINS; ARYL BROMIDES; HECK; PHTHALOCYANINES; SUZUKI;
D O I
10.1016/j.tetlet.2006.09.101
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of mono-functionalized trisulfonated phthalocyanines were prepared in aqueous medium under palladium-catalyzed cross-coupling reaction conditions (Sonogashira, Heck and Suzuki) using water-soluble mono-iodo trisufophthalocyanines as precursors. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8275 / 8278
页数:4
相关论文
共 33 条
  • [1] BIOLOGICAL-ACTIVITIES OF PHTHALOCYANINES .10. SYNTHESES AND ANALYSES OF SULFONATED PHTHALOCYANINES
    ALI, H
    LANGLOIS, R
    WAGNER, JR
    BRASSEUR, N
    PAQUETTE, B
    VANLIER, JE
    [J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1988, 47 (05) : 713 - 717
  • [2] Synthesis of monofunctionalised phthalocyanines using palladium catalysed cross-coupling reactions
    Ali, H
    vanLier, JE
    [J]. TETRAHEDRON LETTERS, 1997, 38 (07) : 1157 - 1160
  • [3] Metal complexes as photo- and radiosensitizers
    Ali, H
    van Lier, JE
    [J]. CHEMICAL REVIEWS, 1999, 99 (09) : 2379 - 2450
  • [4] [Anonymous], 1995, PALLADIUM REAGENTS C, DOI DOI 10.1021/ol101619s
  • [5] PALLADIUM-CATALYZED ALKYLATIONS IN AQUEOUS-MEDIA
    CASALNUOVO, AL
    CALABRESE, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4324 - 4330
  • [6] Structure-photodynamic activity relationships of substituted zinc trisulfophthalocyanines
    Cauchon, N
    Tian, HJ
    Langlois, J
    La Madeleine, C
    Martin, S
    All, H
    Hunting, D
    van Lier, JE
    [J]. BIOCONJUGATE CHEMISTRY, 2005, 16 (01) : 80 - 89
  • [7] Subphthalocyanines:: Singular nonplanar aromatic compounds-synthesis, reactivity, and physical properties
    Claessens, CG
    González-Rodríguez, D
    Torres, T
    [J]. CHEMICAL REVIEWS, 2002, 102 (03) : 835 - 853
  • [8] de Meijere A., 2004, METAL CATALYZED CROS
  • [9] Suzuki cross-coupling of arylboronic acids mediated by a hydrosoluble Pd(0)/TPPTS catalyst
    Dupuis, C
    Adiey, K
    Charruault, L
    Michelet, V
    Savignac, M
    Genêt, JP
    [J]. TETRAHEDRON LETTERS, 2001, 42 (37) : 6523 - 6526
  • [10] Grieco, 1998, ORGANIC SYNTHESIS WA