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Volumn 641, Issue 1-2, 2002, Pages 30-40

Development of new palladium catalysts for the alkoxycarbonylation of aryl chlorides

Author keywords

Aryl chlorides; Benzoic acids; Carbonylation; Ferrocenyl phosphines; Homogeneous catalysis; Palladium

Indexed keywords

BENZOIC ACID; CARBONYLATION; CATALYSIS; CHLORINE COMPOUNDS; PALLADIUM; PHOSPHORUS COMPOUNDS;

EID: 0002807028     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(01)01293-1     Document Type: Article
Times cited : (82)

References (61)
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    • The low reactivity of aryl chlorides in palladium-catalyzed coupling reactions is generally ascribed to their reluctance to undergo oxidative addition to the catalytically active Pd(0) species. The oxidative addition step is accelerated if electron-deficient aryl chlorides are employed and/or the electron density at the Pd(0) metal center is increased, e.g. by the use of basic phosphine ligands. For an excellent recent review see:. Murai S. (Ed), Springer, Berlin
    • The low reactivity of aryl chlorides in palladium-catalyzed coupling reactions is generally ascribed to their reluctance to undergo oxidative addition to the catalytically active Pd(0) species. The oxidative addition step is accelerated if electron-deficient aryl chlorides are employed and/or the electron density at the Pd(0) metal center is increased, e.g. by the use of basic phosphine ligands. For an excellent recent review see:. Grushin V.V., and Alper H. In: Murai S. (Ed). Topics in Organometallic Chemistry 3 (1999), Springer, Berlin 193
    • (1999) Topics in Organometallic Chemistry , vol.3 , pp. 193
    • Grushin, V.V.1    Alper, H.2
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    • A. Ehrentraut, A. Zapf, M. Beller, Angew. Chem. 112 (2000) 4315; Angew. Chem. Int. Ed. Engl. 39 (2000) 4153.
    • A. Ehrentraut, A. Zapf, M. Beller, Angew. Chem. 112 (2000) 4315; Angew. Chem. Int. Ed. Engl. 39 (2000) 4153.
  • 31
    • 0000876608 scopus 로고    scopus 로고
    • For a recent review about palladium carbonyl complexes see: (a) T. A. Stromnova, I. I. Moiseev, Russ. Chem. Rev. 67 (1998) 485;(b) K. Kudo, M. Hidai, Y. Uchida, J. Organomet. Chem. 33 (1971) 393;(c) M. Hidai, K. Kokura, Y. Uchida, J. Organomet. Chem. 52 (1973) 431.
    • For a recent review about palladium carbonyl complexes see: (a) T. A. Stromnova, I. I. Moiseev, Russ. Chem. Rev. 67 (1998) 485;(b) K. Kudo, M. Hidai, Y. Uchida, J. Organomet. Chem. 33 (1971) 393;(c) M. Hidai, K. Kokura, Y. Uchida, J. Organomet. Chem. 52 (1973) 431.
  • 44
    • 67649243618 scopus 로고    scopus 로고
    • note
    • Due to their π-acceptor properties, CO ligands withdraw electron density from the Pd(0) center, thereby hampering the oxidative addition of the aryl chloride substrate.
  • 48
    • 0001898589 scopus 로고    scopus 로고
    • Togni A. Chimia 50 (1996) 86
    • (1996) Chimia , vol.50 , pp. 86
    • Togni, A.1
  • 53
    • 67649246727 scopus 로고    scopus 로고
    • Software: statgraphics plus for Windows 3.1.
    • Software: statgraphics plus for Windows 3.1.
  • 54
    • 67649252968 scopus 로고    scopus 로고
    • note
    • A P/Pd ratio of 80 was chosen in this experiment, i.e. the ligand concentration was kept constant at 2 mol%. A former study of carbonylation reactions has shown that, for a given Pd concentration, the phosphine ligand concentration instead of the P/Pd ratio is the relevant parameter.
  • 55
    • 67649295357 scopus 로고    scopus 로고
    • note
    • A higher TON of 3100 was only reported in an example describing the palladium-catalyzed aminocarbonylation of the strongly activated substrate in 2-position (2,5-dichloropyridine): M. Scalone, P. Vogt, (Hoffmann-La Roche) EP 385 210 A2 (1990); Chem. Abstr. 114 (1991) 143153k.
  • 56
    • 67649271392 scopus 로고    scopus 로고
    • note
    • 2/4 catalyst is more active with electron rich substrates may indicate that the oxidative addition of the aryl chloride is not the rate determining step under the applied conditions.
  • 60
    • 67649271390 scopus 로고    scopus 로고
    • note
    • For experiments at different temperatures, CO pressures, and catalyst concentrations, or with other ligands and bases, the conditions given in the respective tables were used.
  • 61
    • 67649292641 scopus 로고    scopus 로고
    • note
    • Since the mixture of (4-carboxyphenyl)acetic acid and (4-butoxycarbonylphenyl)acetic acid, as isolated from the respective carbonylation experiment, was not separated, only the NMR data of these by-products is given.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.