PH-dependent C-C coupling reactions catalyzed by water-soluble palladacyclic aqua catalysts in water

Seiji Ogo, Yoshitaka Takebe, Keiji Uehara, Takayuki Yamazaki, Hidetaka Nakai, Yoshihito Watanabe, Shunichi Fukuzumi

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    82 Citations (Scopus)

    Abstract

    The series of water-soluble palladacyclic aqua complexes [( tBu-SCS)PdII(H2O)]+ ([1] +, tBu-SCS = C6H3-2,6-(CH 2StBu)2), [(iPr-SCS)Pd II(H2O)]+ ([2]+, iPr-SCS = C6H3-2,6-(CH2SiPr)2), [(PCP)PdII(H2O)]+ ([3]+, PCP = C2H3-2,6-(OPiPr2)2), and [(PC)PdII(H2O)2]+ ([4]+, PC = 4-MeC6H3-2-(OPiPr2)) have been synthesized from the reaction of the corresponding palladacyclic chloro complexes with silver salts in water to optimize the catalytic activity for pH-dependent C-C coupling reactions in water by changing the supporting ligands from S-supporting (SCS) to P-supporting (PCP) ligands and also from tridentate (PCP) to bidentate (PC) ligands. It was confirmed that there was no precipitation of palladium black under the present reaction conditions. The PC palladacyclic aqua complex [4]+ exhibits the highest catalytic activity among the water-soluble palladacyclic aqua complexes [1] +-[4]+ for the pH-dependent Suzuki Miyaura, Mizoroki-Heck, and Stille coupling reactions in water. This is one of the highest catalytic activities ever reported for coupling reactions with water-soluble palladium catalysts in water. The catalytic abilily of the palladacyclic aqua catalysts is drastically dependent on the pH of the solution and the structures of supporting ligands. The structures of palladacyclic aqua and chloro complexes were unequivocally determined by X-ray analysis.

    Original languageEnglish
    Pages (from-to)331-338
    Number of pages8
    JournalOrganometallics
    Volume25
    Issue number2
    DOIs
    Publication statusPublished - Jan 16 2006

    All Science Journal Classification (ASJC) codes

    • Physical and Theoretical Chemistry
    • Organic Chemistry
    • Inorganic Chemistry

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