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Volumn 22, Issue 21, 2003, Pages 4193-4197

Pd nanoparticle catalyzed Heck arylation of 1,1-disubstituted alkenes in ionic liquids. Study on factors affecting the regioselectivity of the coupling process

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMMONIUM COMPOUNDS; CATALYSIS; CATALYST SELECTIVITY; ISOMERS; NANOSTRUCTURED MATERIALS; ORGANIC SOLVENTS; PALLADIUM; REACTION KINETICS; STYRENE; SUBSTITUTION REACTIONS;

EID: 0242303166     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om034020w     Document Type: Article
Times cited : (108)

References (68)
  • 10
    • 0029869371 scopus 로고    scopus 로고
    • This system was applied to the vinylation of enones
    • Arcadi, A.; Cacchi, S.; Fabrizi, G.; Pace, P. Tetrahedron 1996, 52, 6983-6986. This system was applied to the vinylation of enones.
    • (1996) Tetrahedron , vol.52 , pp. 6983-6986
    • Arcadi, A.1    Cacchi, S.2    Fabrizi, G.3    Pace, P.4
  • 22
    • 33748818767 scopus 로고
    • For regio- and stereocontrolled synthesis of di- and trisubstituted olefins starting from vinylsilanes by the Heck reaction see: (d) Schimpf, R.; Tietze, L. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1089-1091.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1089-1091
    • Schimpf, R.1    Tietze, L.F.2
  • 32
    • 0242295456 scopus 로고    scopus 로고
    • Herkes, F. E., Ed.; Marcel Dekker: New York; Chapter 33
    • (c) Eisestadt, A. In Catalysis of Organic Reactions; Herkes, F. E., Ed.; Marcel Dekker: New York, 1998; Chapter 33.
    • (1998) Catalysis of Organic Reactions
    • Eisestadt, A.1
  • 62
    • 0032490909 scopus 로고    scopus 로고
    • For the application of tetraalkylammonium salts in the Heck reaction see: Jeffery, T.; David, M. Tetrahedron Lett. 1998, 39, 5751-5754.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 5751-5754
    • Jeffery, T.1    David, M.2
  • 64
    • 0242295450 scopus 로고    scopus 로고
    • note
    • This fast isomerization could be due to the benzylic hydrogen, whose acidity, by favoring a fast isomerization of the terminal isomer, inhibits further arylation into the double-arylated product.
  • 65
    • 0242295451 scopus 로고    scopus 로고
    • note
    • a values of acetate and pivalate anions in TBAB cannot be the same as those measured in water. This would not be surprising, since in these solvents the anions, being poorly solvated, should be both good nucleophiles for palladium and stronger bases.
  • 66
    • 0001589134 scopus 로고
    • note
    • Evidence for ligation of acetate ion to Pd(0) and Pd(II) intermediates was reported: Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A.; Meyer, G. Organometallics 1995, 14, 5605-5614. Our data, however, cannot discriminate whether the PdH neutralization by acetate is an intermolecular process or an intramolecular one by acetate ligand in the metal coordination shell.
    • (1995) Organometallics , vol.14 , pp. 5605-5614
    • Amatore, C.1    Carré, E.2    Jutand, A.3    M'Barki, M.A.4    Meyer, G.5
  • 67
    • 0242326963 scopus 로고    scopus 로고
    • note
    • Due to predominant formation of E product from the less sterically hindered conformer, statistical weights of the two routes leading to E and Z internal olefins are not equal, as the route leading to the Z diastereomer can be neglected.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.