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Volumn 5, Issue 8, 2003, Pages 1197-1200

Remarkable dendritic effect in the polymer-supported catalysis of the heck arylation of olefins

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; POLYMER; POLYSTYRENE;

EID: 0041480399     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0340181     Document Type: Article
Times cited : (122)

References (47)
  • 8
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    • For positive dendritic effects in solution, see: (a) Lee, J.-J.; Ford, W. T.; Moore, J. A.; Li, X. Macromolecules 1994, 27, 4632. (b) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604. (c) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361. (d) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 52.
    • (1994) Macromolecules , vol.27 , pp. 4632
    • Lee, J.-J.1    Ford, W.T.2    Moore, J.A.3    Li, X.4
  • 9
    • 0034675617 scopus 로고    scopus 로고
    • For positive dendritic effects in solution, see: (a) Lee, J.-J.; Ford, W. T.; Moore, J. A.; Li, X. Macromolecules 1994, 27, 4632. (b) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604. (c) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361. (d) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 52.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 3604
    • Breinbauer, R.1    Jacobsen, E.N.2
  • 10
    • 0035925139 scopus 로고    scopus 로고
    • For positive dendritic effects in solution, see: (a) Lee, J.-J.; Ford, W. T.; Moore, J. A.; Li, X. Macromolecules 1994, 27, 4632. (b) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604. (c) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361. (d) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 52.
    • (2001) Chem. Commun. , pp. 361
    • Ropartz, L.1    Morris, R.E.2    Foster, D.F.3    Cole-Hamilton, D.J.4
  • 11
    • 0035835056 scopus 로고    scopus 로고
    • For positive dendritic effects in solution, see: (a) Lee, J.-J.; Ford, W. T.; Moore, J. A.; Li, X. Macromolecules 1994, 27, 4632. (b) Breinbauer, R.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 3604. (c) Ropartz, L.; Morris, R. E.; Foster, D. F.; Cole-Hamilton, D. J. Chem. Commun. 2001, 361. (d) Francavilla, C.; Drake, M. D.; Bright, F. V.; Detty, M. R. J. Am. Chem. Soc. 2001, 123, 52.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 52
    • Francavilla, C.1    Drake, M.D.2    Bright, F.V.3    Detty, M.R.4
  • 20
    • 0000550963 scopus 로고    scopus 로고
    • For polyamine-based soluble dendritic catalyst for this reaction, see: (a) Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1526. (b) Reetz, M. T. Top. Catal. 1997, 4, 187.
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    • For rare examples of supported systems capable of unactivated bromoarene olefination, see: (a) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101. (b) Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche, M.; Herrman, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem. Eur. J. 2000, 6, 1773. (c) Dell'Anna, M. M.; Mastrorilli, P.; Muscio, F.; Nobile, C. F.; Surranna, G. P. Eur. J. Inorg. Chem. 2002, 1094.
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  • 27
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    • For rare examples of supported systems capable of unactivated bromoarene olefination, see: (a) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101. (b) Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche, M.; Herrman, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem. Eur. J. 2000, 6, 1773. (c) Dell'Anna, M. M.; Mastrorilli, P.; Muscio, F.; Nobile, C. F.; Surranna, G. P. Eur. J. Inorg. Chem. 2002, 1094.
    • (2000) Chem. Eur. J. , vol.6 , pp. 1773
    • Schwarz, J.1    Böhm, V.P.W.2    Gardiner, M.G.3    Grosche, M.4    Herrman, W.A.5    Hieringer, W.6    Raudaschl-Sieber, G.7
  • 28
    • 0036236712 scopus 로고    scopus 로고
    • For rare examples of supported systems capable of unactivated bromoarene olefination, see: (a) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101. (b) Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche, M.; Herrman, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem. Eur. J. 2000, 6, 1773. (c) Dell'Anna, M. M.; Mastrorilli, P.; Muscio, F.; Nobile, C. F.; Surranna, G. P. Eur. J. Inorg. Chem. 2002, 1094.
    • (2002) Eur. J. Inorg. Chem. , pp. 1094
    • Dell'Anna, M.M.1    Mastrorilli, P.2    Muscio, F.3    Nobile, C.F.4    Surranna, G.P.5
  • 29
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    • and references therein
    • For rare metal palladium catalysts capable of unactivated bromoarene olefination, see: (a) Köhler, K.; Wagner, M.; Djakovitch, L. Catal. Today 2001, 66, 105 and references therein. (b) Mehnert, C. P.; Ying, T. Y. Chem. Commun. 1997, 2215. (c) Köhler, K.; Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J. Chem. Eur. J. 2002, 8, 622.
    • (2001) Catal. Today , vol.66 , pp. 105
    • Köhler, K.1    Wagner, M.2    Djakovitch, L.3
  • 30
    • 0001862762 scopus 로고    scopus 로고
    • For rare metal palladium catalysts capable of unactivated bromoarene olefination, see: (a) Köhler, K.; Wagner, M.; Djakovitch, L. Catal. Today 2001, 66, 105 and references therein. (b) Mehnert, C. P.; Ying, T. Y. Chem. Commun. 1997, 2215. (c) Köhler, K.; Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J. Chem. Eur. J. 2002, 8, 622.
    • (1997) Chem. Commun. , pp. 2215
    • Mehnert, C.P.1    Ying, T.Y.2
  • 31
    • 0037006237 scopus 로고    scopus 로고
    • For rare metal palladium catalysts capable of unactivated bromoarene olefination, see: (a) Köhler, K.; Wagner, M.; Djakovitch, L. Catal. Today 2001, 66, 105 and references therein. (b) Mehnert, C. P.; Ying, T. Y. Chem. Commun. 1997, 2215. (c) Köhler, K.; Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J. Chem. Eur. J. 2002, 8, 622.
    • (2002) Chem. Eur. J. , vol.8 , pp. 622
    • Köhler, K.1    Heidenreich, R.G.2    Krauter, J.G.E.3    Pietsch, J.4
  • 41
    • 0141549315 scopus 로고    scopus 로고
    • note
    • Loading of phosphine groups: 1a, 0.89 mmol/g; 1b, 0.82 mmol/g; 1c, 1.12 mmol/g; 1d, 0.70 mmol/g
  • 42
    • 0141772623 scopus 로고    scopus 로고
    • note
    • Loading of palladium: 2a, 0.38 mmol/g; 2b, 0.36 mmol/g; 2c, 0.47 mmol/g; 2d, 0.31 mmol/g
  • 43
    • 0141437743 scopus 로고    scopus 로고
    • note
    • Although monodentate phosphine is used for preparation of 6, the minimal chelate size on dendronized resins is 20 atoms and thus chelate effects are not likely to be responsible for the observed phenomenon.
  • 46
    • 0141660694 scopus 로고    scopus 로고
    • As observed in ref 6a
    • As observed in ref 6a.
  • 47
    • 0141549316 scopus 로고    scopus 로고
    • note
    • According to ref 11, phosphine-Pd complexes as catalysts yield a ca. 2.5:1 ratio, while the "naked" Pd catalysts form 1:1 product mixtures.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.