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Volumn 72, Issue 3, 1999, Pages 573-580

Preparation of acyl(carboxylato)bis(tertiary phosphine)palladium(II) complexes by C-O bond cleavage of carboxylic anhydrides on interaction with palladium(0) complexes. Catalytic hydrogenation of carboxylic anhydrides to aldehydes by palladium complexes

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; ALDEHYDE; CARBOXYLIC ANHYDRIDE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

EID: 0032935371     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.72.573     Document Type: Article
Times cited : (44)

References (71)
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    • Other studies on C-O bond activation of anhydrides by transition metal complexes: Mn: H. Berke and G. Weiler, Angew. Chem., Int. Ed. Engl., 21, 150 (1982); Fe: J. P. Collman and S. R. Winter, J. Am. Chem. Soc., 95, 4089 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Tanaka, and Y. Takegami, Tetrahedron Lett., 37, 3535 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, K. Tomi, and Y. Takegami, Tetrahedron Lett., 12, 1063 (1975); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, and Y. Takegami, Bull. Chem. Soc. Jpn., 48, 2490 (1975); Ru: T. Ikariya, K. Osakada, and S. Yoshikawa, Tetrahedron Lett., 39, 3749 (1978); K. Osakada, T. Ikariya, and S. Yoshikawa, J. Organomet. Chem., 231, 79 (1982); Rh: J. A. Miller and J. A. Nelson, Organometallics, 10, 2958 (1991); Ir: D. M. Blake, S. Shields, and L. Wyman, Inorg. Chem., 13, 1595 (1974); J. A. van Doom, C. Masters, and C. van der Woude, J. Organomet. Chem., 141, 231 (1977).
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    • Other studies on C-O bond activation of anhydrides by transition metal complexes: Mn: H. Berke and G. Weiler, Angew. Chem., Int. Ed. Engl., 21, 150 (1982); Fe: J. P. Collman and S. R. Winter, J. Am. Chem. Soc., 95, 4089 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Tanaka, and Y. Takegami, Tetrahedron Lett., 37, 3535 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, K. Tomi, and Y. Takegami, Tetrahedron Lett., 12, 1063 (1975); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, and Y. Takegami, Bull. Chem. Soc. Jpn., 48, 2490 (1975); Ru: T. Ikariya, K. Osakada, and S. Yoshikawa, Tetrahedron Lett., 39, 3749 (1978); K. Osakada, T. Ikariya, and S. Yoshikawa, J. Organomet. Chem., 231, 79 (1982); Rh: J. A. Miller and J. A. Nelson, Organometallics, 10, 2958 (1991); Ir: D. M. Blake, S. Shields, and L. Wyman, Inorg. Chem., 13, 1595 (1974); J. A. van Doom, C. Masters, and C. van der Woude, J. Organomet. Chem., 141, 231 (1977).
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    • Other studies on C-O bond activation of anhydrides by transition metal complexes: Mn: H. Berke and G. Weiler, Angew. Chem., Int. Ed. Engl., 21, 150 (1982); Fe: J. P. Collman and S. R. Winter, J. Am. Chem. Soc., 95, 4089 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Tanaka, and Y. Takegami, Tetrahedron Lett., 37, 3535 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, K. Tomi, and Y. Takegami, Tetrahedron Lett., 12, 1063 (1975); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, and Y. Takegami, Bull. Chem. Soc. Jpn., 48, 2490 (1975); Ru: T. Ikariya, K. Osakada, and S. Yoshikawa, Tetrahedron Lett., 39, 3749 (1978); K. Osakada, T. Ikariya, and S. Yoshikawa, J. Organomet. Chem., 231, 79 (1982); Rh: J. A. Miller and J. A. Nelson, Organometallics, 10, 2958 (1991); Ir: D. M. Blake, S. Shields, and L. Wyman, Inorg. Chem., 13, 1595 (1974); J. A. van Doom, C. Masters, and C. van der Woude, J. Organomet. Chem., 141, 231 (1977).
    • (1975) Tetrahedron Lett. , vol.12 , pp. 1063
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    • Other studies on C-O bond activation of anhydrides by transition metal complexes: Mn: H. Berke and G. Weiler, Angew. Chem., Int. Ed. Engl., 21, 150 (1982); Fe: J. P. Collman and S. R. Winter, J. Am. Chem. Soc., 95, 4089 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Tanaka, and Y. Takegami, Tetrahedron Lett., 37, 3535 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, K. Tomi, and Y. Takegami, Tetrahedron Lett., 12, 1063 (1975); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, and Y. Takegami, Bull. Chem. Soc. Jpn., 48, 2490 (1975); Ru: T. Ikariya, K. Osakada, and S. Yoshikawa, Tetrahedron Lett., 39, 3749 (1978); K. Osakada, T. Ikariya, and S. Yoshikawa, J. Organomet. Chem., 231, 79 (1982); Rh: J. A. Miller and J. A. Nelson, Organometallics, 10, 2958 (1991); Ir: D. M. Blake, S. Shields, and L. Wyman, Inorg. Chem., 13, 1595 (1974); J. A. van Doom, C. Masters, and C. van der Woude, J. Organomet. Chem., 141, 231 (1977).
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    • Watanabe, Y.1    Yamashita, M.2    Mitsudo, T.3    Igami, M.4    Takegami, Y.5
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    • Other studies on C-O bond activation of anhydrides by transition metal complexes: Mn: H. Berke and G. Weiler, Angew. Chem., Int. Ed. Engl., 21, 150 (1982); Fe: J. P. Collman and S. R. Winter, J. Am. Chem. Soc., 95, 4089 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Tanaka, and Y. Takegami, Tetrahedron Lett., 37, 3535 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, K. Tomi, and Y. Takegami, Tetrahedron Lett., 12, 1063 (1975); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, and Y. Takegami, Bull. Chem. Soc. Jpn., 48, 2490 (1975); Ru: T. Ikariya, K. Osakada, and S. Yoshikawa, Tetrahedron Lett., 39, 3749 (1978); K. Osakada, T. Ikariya, and S. Yoshikawa, J. Organomet. Chem., 231, 79 (1982); Rh: J. A. Miller and J. A. Nelson, Organometallics, 10, 2958 (1991); Ir: D. M. Blake, S. Shields, and L. Wyman, Inorg. Chem., 13, 1595 (1974); J. A. van Doom, C. Masters, and C. van der Woude, J. Organomet. Chem., 141, 231 (1977).
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    • Ikariya, T.1    Osakada, K.2    Yoshikawa, S.3
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    • Other studies on C-O bond activation of anhydrides by transition metal complexes: Mn: H. Berke and G. Weiler, Angew. Chem., Int. Ed. Engl., 21, 150 (1982); Fe: J. P. Collman and S. R. Winter, J. Am. Chem. Soc., 95, 4089 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Tanaka, and Y. Takegami, Tetrahedron Lett., 37, 3535 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, K. Tomi, and Y. Takegami, Tetrahedron Lett., 12, 1063 (1975); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, and Y. Takegami, Bull. Chem. Soc. Jpn., 48, 2490 (1975); Ru: T. Ikariya, K. Osakada, and S. Yoshikawa, Tetrahedron Lett., 39, 3749 (1978); K. Osakada, T. Ikariya, and S. Yoshikawa, J. Organomet. Chem., 231, 79 (1982); Rh: J. A. Miller and J. A. Nelson, Organometallics, 10, 2958 (1991); Ir: D. M. Blake, S. Shields, and L. Wyman, Inorg. Chem., 13, 1595 (1974); J. A. van Doom, C. Masters, and C. van der Woude, J. Organomet. Chem., 141, 231 (1977).
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    • Osakada, K.1    Ikariya, T.2    Yoshikawa, S.3
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    • Other studies on C-O bond activation of anhydrides by transition metal complexes: Mn: H. Berke and G. Weiler, Angew. Chem., Int. Ed. Engl., 21, 150 (1982); Fe: J. P. Collman and S. R. Winter, J. Am. Chem. Soc., 95, 4089 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Tanaka, and Y. Takegami, Tetrahedron Lett., 37, 3535 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, K. Tomi, and Y. Takegami, Tetrahedron Lett., 12, 1063 (1975); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, and Y. Takegami, Bull. Chem. Soc. Jpn., 48, 2490 (1975); Ru: T. Ikariya, K. Osakada, and S. Yoshikawa, Tetrahedron Lett., 39, 3749 (1978); K. Osakada, T. Ikariya, and S. Yoshikawa, J. Organomet. Chem., 231, 79 (1982); Rh: J. A. Miller and J. A. Nelson, Organometallics, 10, 2958 (1991); Ir: D. M. Blake, S. Shields, and L. Wyman, Inorg. Chem., 13, 1595 (1974); J. A. van Doom, C. Masters, and C. van der Woude, J. Organomet. Chem., 141, 231 (1977).
    • (1991) Organometallics , vol.10 , pp. 2958
    • Miller, J.A.1    Nelson, J.A.2
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    • 0013559370 scopus 로고
    • Other studies on C-O bond activation of anhydrides by transition metal complexes: Mn: H. Berke and G. Weiler, Angew. Chem., Int. Ed. Engl., 21, 150 (1982); Fe: J. P. Collman and S. R. Winter, J. Am. Chem. Soc., 95, 4089 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Tanaka, and Y. Takegami, Tetrahedron Lett., 37, 3535 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, K. Tomi, and Y. Takegami, Tetrahedron Lett., 12, 1063 (1975); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, and Y. Takegami, Bull. Chem. Soc. Jpn., 48, 2490 (1975); Ru: T. Ikariya, K. Osakada, and S. Yoshikawa, Tetrahedron Lett., 39, 3749 (1978); K. Osakada, T. Ikariya, and S. Yoshikawa, J. Organomet. Chem., 231, 79 (1982); Rh: J. A. Miller and J. A. Nelson, Organometallics, 10, 2958 (1991); Ir: D. M. Blake, S. Shields, and L. Wyman, Inorg. Chem., 13, 1595 (1974); J. A. van Doom, C. Masters, and C. van der Woude, J. Organomet. Chem., 141, 231 (1977).
    • (1974) Inorg. Chem. , vol.13 , pp. 1595
    • Blake, D.M.1    Shields, S.2    Wyman, L.3
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    • 0013493302 scopus 로고
    • Other studies on C-O bond activation of anhydrides by transition metal complexes: Mn: H. Berke and G. Weiler, Angew. Chem., Int. Ed. Engl., 21, 150 (1982); Fe: J. P. Collman and S. R. Winter, J. Am. Chem. Soc., 95, 4089 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Tanaka, and Y. Takegami, Tetrahedron Lett., 37, 3535 (1973); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, K. Tomi, and Y. Takegami, Tetrahedron Lett., 12, 1063 (1975); Y. Watanabe, M. Yamashita, T. Mitsudo, M. Igami, and Y. Takegami, Bull. Chem. Soc. Jpn., 48, 2490 (1975); Ru: T. Ikariya, K. Osakada, and S. Yoshikawa, Tetrahedron Lett., 39, 3749 (1978); K. Osakada, T. Ikariya, and S. Yoshikawa, J. Organomet. Chem., 231, 79 (1982); Rh: J. A. Miller and J. A. Nelson, Organometallics, 10, 2958 (1991); Ir: D. M. Blake, S. Shields, and L. Wyman, Inorg. Chem., 13, 1595 (1974); J. A. van Doom, C. Masters, and C. van der Woude, J. Organomet. Chem., 141, 231 (1977).
    • (1977) J. Organomet. Chem. , vol.141 , pp. 231
    • Van Doom, J.A.1    Masters, C.2    Van Der Woude, C.3
  • 58
    • 85038182301 scopus 로고    scopus 로고
    • note
    • The acyl(carboxylato)bis(tertiary phosphine)palladium complexes have been also synthesized by the reaction of corresponding alkyl(carboxylato)bis(tertiary phosphine)palladium complexes with CO; see Ref. 5c.
  • 61
    • 0000686285 scopus 로고
    • and references cited therein
    • Preparation of similar SPh-coordinated palladium complexes have been reported: K. Osakada, Y. Ozawa, and A. Yamamoto, Bull. Chem. Soc. Jpn., 64, 2002 (1991), and references cited therein.
    • (1991) Bull. Chem. Soc. Jpn. , vol.64 , pp. 2002
    • Osakada, K.1    Ozawa, Y.2    Yamamoto, A.3
  • 63
    • 85038190840 scopus 로고    scopus 로고
    • note
    • Ethanol may have been formed via further hydrogenation of acetaldehyde catalyzed by zerovalent palladium species generated in the system. See Ref. 3i.
  • 68
    • 0000415257 scopus 로고
    • ) Homogeneous Rosenmund reduction of aroyl halides to aldehydes catalyzed by palladium complexes has been achieved by Heck et al.: A. Schoenberg and R. F. Heck, J. Am. Chem. Soc., 96, 7761 (1974).
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 7761
    • Schoenberg, A.1    Heck, R.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.