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Volumn 25, Issue 2, 2006, Pages 491-505

Modular chelated palladium diaminocarbene complexes: Synthesis, characterization, and optimization of catalytic Suzuki-Miyaura cross-coupling activity by ligand modification

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLISOCYANIDES; CHELATING LIGANDS; PALLADIUM DIAMINOCARBENE COMPLEXES; SUZUKI-MIYAURA COUPLINGS;

EID: 31544482131     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050786f     Document Type: Article
Times cited : (90)

References (142)
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    • Chelating NHC ligands have been successfully employed in the following catalytic reactions. Pd-catalyzed Heck coupling: (a) Peris, E.; Loch, J. A.; Mata, J.; Crabtree, R. H. Chem. Commun. 2001, 201-202. Pd-catalyzed Suzuki-Miyaura coupling:
    • (2001) Chem. Commun. , pp. 201-202
    • Peris, E.1    Loch, J.A.2    Mata, J.3    Crabtree, R.H.4
  • 66
    • 31544483250 scopus 로고    scopus 로고
    • note
    • The English transliteration "Chugaev" is cited in Chemical Abstracts and most English language journals, whereas "Tschugajeff" is employed in the German literature.
  • 92
    • 0037415847 scopus 로고    scopus 로고
    • An elegant strategy reported for the metal-templated synthesis of cyclic monodentale diaminocarbene ligands employs β-functionalized arylisocyanides that spontaneously cyclize at the metal center: (a) Hahn, F. E.; Langenhahn, V.; Meier, N.; Lügger, T.; Fehlhammer, W. P. Chem. Eur. J. 2003, 9, 704-712.
    • (2003) Chem. Eur. J. , vol.9 , pp. 704-712
    • Hahn, F.E.1    Langenhahn, V.2    Meier, N.3    Lügger, T.4    Fehlhammer, W.P.5
  • 93
    • 10944245779 scopus 로고    scopus 로고
    • (b) Hahn, F. E.; Plumed, C. G.; Münder, M.; Lügger, T. Chem. Eur. J. 2004, 10, 6285-6293. Subsequent modification of these NH-containing carbenes into a tetradentate chelating carbene at Pt has been demonstrated:
    • (2004) Chem. Eur. J. , vol.10 , pp. 6285-6293
    • Hahn, F.E.1    Plumed, C.G.2    Münder, M.3    Lügger, T.4
  • 105
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    • note
    • 23,33c
  • 107
    • 31544478744 scopus 로고    scopus 로고
    • note
    • Similar N⋯Br distances were observed for complexes 3b-3d: see Table S2 (Supporting Information) for relevant data.
  • 110
    • 31544475068 scopus 로고    scopus 로고
    • note
    • The latter example (4-chloroacetophenone + phenylboronic acid) was not reported in ref 65.
  • 121
    • 0003791302 scopus 로고    scopus 로고
    • Part A: Structure and Mechanisms; Kluwer Academic/Plenum Publishers: New York
    • Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 4th ed.; Part A: Structure and Mechanisms; Kluwer Academic/Plenum Publishers: New York, 2000; pp 204-215, 243-246.
    • (2000) Advanced Organic Chemistry, 4th Ed. , pp. 204-215
    • Carey, F.A.1    Sundberg, R.J.2
  • 131
    • 0000461962 scopus 로고
    • For kinetic evidence for the intermediacy of a palladium(O)monophosphine species in aryl bromide oxidative addition, see: Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373-5374.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5373-5374
    • Hartwig, J.F.1    Paul, F.2
  • 134
    • 31544456282 scopus 로고    scopus 로고
    • note
    • Two reports have demonstrated high-yield Suzuki-Miyaura couplings of aryl bromides and chlorides at 80°C using palladium catalysts generated in situ from bis-imidazolium salts (refs 25b,c). However, it is not known whether chelated palladium intermediates are the active catalysts in these systems.
  • 137
    • 0003587328 scopus 로고    scopus 로고
    • Bruker AXS: Madison, WI
    • SAINT-plus, Version 6.29; Bruker AXS: Madison, WI, 2001.
    • (2001) SAINT-plus, Version 6.29
  • 139
    • 0004150157 scopus 로고    scopus 로고
    • structure solution
    • SHELXS (structure solution, 1990);
    • (1990) SHELXS
  • 140
    • 0004150157 scopus 로고    scopus 로고
    • structure refinement
    • SHELXL (structure refinement, 1997);
    • (1997) SHELXL
  • 141


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.