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

Research output: Contribution to journalArticle

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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

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catalysts
Catalysts
Water
water
Ligands
catalytic activity
Catalyst activity
ligands
Palladium
palladium
X ray analysis
Silver
Salts
silver
methylidyne
salts
x rays

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Ogo, S., Takebe, Y., Uehara, K., Yamazaki, T., Nakai, H., Watanabe, Y., & Fukuzumi, S. (2006). PH-dependent C-C coupling reactions catalyzed by water-soluble palladacyclic aqua catalysts in water. Organometallics, 25(2), 331-338. https://doi.org/10.1021/om0503592

PH-dependent C-C coupling reactions catalyzed by water-soluble palladacyclic aqua catalysts in water. / Ogo, Seiji; Takebe, Yoshitaka; Uehara, Keiji; Yamazaki, Takayuki; Nakai, Hidetaka; Watanabe, Yoshihito; Fukuzumi, Shunichi.

In: Organometallics, Vol. 25, No. 2, 16.01.2006, p. 331-338.

Research output: Contribution to journalArticle

Ogo, S, Takebe, Y, Uehara, K, Yamazaki, T, Nakai, H, Watanabe, Y & Fukuzumi, S 2006, 'PH-dependent C-C coupling reactions catalyzed by water-soluble palladacyclic aqua catalysts in water', Organometallics, vol. 25, no. 2, pp. 331-338. https://doi.org/10.1021/om0503592
Ogo, Seiji ; Takebe, Yoshitaka ; Uehara, Keiji ; Yamazaki, Takayuki ; Nakai, Hidetaka ; Watanabe, Yoshihito ; Fukuzumi, Shunichi. / PH-dependent C-C coupling reactions catalyzed by water-soluble palladacyclic aqua catalysts in water. In: Organometallics. 2006 ; Vol. 25, No. 2. pp. 331-338.
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