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Volumn , Issue 6, 2003, Pages 1161-1168

[Bis(oxazolinyl)pyrrole]palladium complexes as catalysts in heck- and suzuki-type C-C coupling reactions

Author keywords

Catalysis; Heck reaction; Helical structures; N ligands; Palladium; Suzuki reaction

Indexed keywords

CATALYSTS; INDIUM COMPOUNDS; LIGANDS; LITHIUM COMPOUNDS; STYRENE;

EID: 0037356545     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejic.200390148     Document Type: Article
Times cited : (31)

References (81)
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    • [2a] R. E. Lowenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 1990, 31, 6005-6008. [2b] D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728. [2c] D. Müller, G. Umbricht, B. Weber, A. Pfaltz, Helv. Chim. Acta 1991, 74, 232-240. [2d] E. J. Corey, N. Imai, H. Y. Zhang, J. Am. Chem. Soc. 1991, 113, 728-729. For reviews of chiral oxazoline ligands in asymmetric catalysis, see: [2e] F. Fache, E. Schulz, M. Lorraine Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159-2231. [2f] M. Gomez, G. Muller, M. Rocamora, Coord. Chem. Rev. 1999, 193, 769-835. [2g] A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45.
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    • Corey, E.J.1    Imai, N.2    Zhang, H.Y.3
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    • 0033714636 scopus 로고    scopus 로고
    • [2a] R. E. Lowenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 1990, 31, 6005-6008. [2b] D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728. [2c] D. Müller, G. Umbricht, B. Weber, A. Pfaltz, Helv. Chim. Acta 1991, 74, 232-240. [2d] E. J. Corey, N. Imai, H. Y. Zhang, J. Am. Chem. Soc. 1991, 113, 728-729. For reviews of chiral oxazoline ligands in asymmetric catalysis, see: [2e] F. Fache, E. Schulz, M. Lorraine Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159-2231. [2f] M. Gomez, G. Muller, M. Rocamora, Coord. Chem. Rev. 1999, 193, 769-835. [2g] A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45.
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    • Fache, F.1    Schulz, E.2    Lorraine Tommasino, M.3    Lemaire, M.4
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    • 0033303725 scopus 로고    scopus 로고
    • [2a] R. E. Lowenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 1990, 31, 6005-6008. [2b] D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728. [2c] D. Müller, G. Umbricht, B. Weber, A. Pfaltz, Helv. Chim. Acta 1991, 74, 232-240. [2d] E. J. Corey, N. Imai, H. Y. Zhang, J. Am. Chem. Soc. 1991, 113, 728-729. For reviews of chiral oxazoline ligands in asymmetric catalysis, see: [2e] F. Fache, E. Schulz, M. Lorraine Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159-2231. [2f] M. Gomez, G. Muller, M. Rocamora, Coord. Chem. Rev. 1999, 193, 769-835. [2g] A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45.
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    • 0032536002 scopus 로고    scopus 로고
    • [2a] R. E. Lowenthal, A. Abiko, S. Masamune, Tetrahedron Lett. 1990, 31, 6005-6008. [2b] D. A. Evans, K. A. Woerpel, M. M. Hinman, M. M. Faul, J. Am. Chem. Soc. 1991, 113, 726-728. [2c] D. Müller, G. Umbricht, B. Weber, A. Pfaltz, Helv. Chim. Acta 1991, 74, 232-240. [2d] E. J. Corey, N. Imai, H. Y. Zhang, J. Am. Chem. Soc. 1991, 113, 728-729. For reviews of chiral oxazoline ligands in asymmetric catalysis, see: [2e] F. Fache, E. Schulz, M. Lorraine Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159-2231. [2f] M. Gomez, G. Muller, M. Rocamora, Coord. Chem. Rev. 1999, 193, 769-835. [2g] A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry 1998, 9, 1-45.
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    • 0034817259 scopus 로고    scopus 로고
    • Selected recent references: [3a] Mukaiyama-Michael reactions: D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480-4491. [3b] Cycloadditions of silyl ketenes: D. A. Evans, J. M. Janey, Org. Lett. 2001, 3, 2125-2128. [3c] Henry reactions: C. Christensen, K. Juhl, K. A. Jorgensen, Chem. Commun. 2001, 2222-2223. [3d] Friedel-Crafts reactions: W. Zhuang, N. Gathergood, R. G. Hazell, K. A. Jorgensen, J. Org. Chem. 2001, 66, 1009-1013- [3e] Hetero Diels-Alder reactions: D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635-1649. [3f] Molybdenum-catalysed allylic alkylation: F. Glorius, A. Pfaltz, Org. Lett. 1999, 1, 141-144.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4480-4491
    • Evans, D.A.1    Scheidt, K.A.2    Johnston, J.N.3    Willis, M.C.4
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    • 0001320447 scopus 로고    scopus 로고
    • Selected recent references: [3a] Mukaiyama-Michael reactions: D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480-4491. [3b] Cycloadditions of silyl ketenes: D. A. Evans, J. M. Janey, Org. Lett. 2001, 3, 2125-2128. [3c] Henry reactions: C. Christensen, K. Juhl, K. A. Jorgensen, Chem. Commun. 2001, 2222-2223. [3d] Friedel-Crafts reactions: W. Zhuang, N. Gathergood, R. G. Hazell, K. A. Jorgensen, J. Org. Chem. 2001, 66, 1009-1013- [3e] Hetero Diels-Alder reactions: D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635-1649. [3f] Molybdenum-catalysed allylic alkylation: F. Glorius, A. Pfaltz, Org. Lett. 1999, 1, 141-144.
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    • Evans, D.A.1    Janey, J.M.2
  • 12
    • 0035824018 scopus 로고    scopus 로고
    • Selected recent references: [3a] Mukaiyama-Michael reactions: D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480-4491. [3b] Cycloadditions of silyl ketenes: D. A. Evans, J. M. Janey, Org. Lett. 2001, 3, 2125-2128. [3c] Henry reactions: C. Christensen, K. Juhl, K. A. Jorgensen, Chem. Commun. 2001, 2222-2223. [3d] Friedel-Crafts reactions: W. Zhuang, N. Gathergood, R. G. Hazell, K. A. Jorgensen, J. Org. Chem. 2001, 66, 1009-1013- [3e] Hetero Diels-Alder reactions: D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635-1649. [3f] Molybdenum-catalysed allylic alkylation: F. Glorius, A. Pfaltz, Org. Lett. 1999, 1, 141-144.
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    • Christensen, C.1    Juhl, K.2    Jorgensen, K.A.3
  • 13
    • 0035830539 scopus 로고    scopus 로고
    • Selected recent references: [3a] Mukaiyama-Michael reactions: D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480-4491. [3b] Cycloadditions of silyl ketenes: D. A. Evans, J. M. Janey, Org. Lett. 2001, 3, 2125-2128. [3c] Henry reactions: C. Christensen, K. Juhl, K. A. Jorgensen, Chem. Commun. 2001, 2222-2223. [3d] Friedel-Crafts reactions: W. Zhuang, N. Gathergood, R. G. Hazell, K. A. Jorgensen, J. Org. Chem. 2001, 66, 1009-1013- [3e] Hetero Diels-Alder reactions: D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635-1649. [3f] Molybdenum-catalysed allylic alkylation: F. Glorius, A. Pfaltz, Org. Lett. 1999, 1, 141-144.
    • (2001) J. Org. Chem. , vol.66 , pp. 1009-1013
    • Zhuang, W.1    Gathergood, N.2    Hazell, R.G.3    Jorgensen, K.A.4
  • 14
    • 0034006954 scopus 로고    scopus 로고
    • Selected recent references: [3a] Mukaiyama-Michael reactions: D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480-4491. [3b] Cycloadditions of silyl ketenes: D. A. Evans, J. M. Janey, Org. Lett. 2001, 3, 2125-2128. [3c] Henry reactions: C. Christensen, K. Juhl, K. A. Jorgensen, Chem. Commun. 2001, 2222-2223. [3d] Friedel-Crafts reactions: W. Zhuang, N. Gathergood, R. G. Hazell, K. A. Jorgensen, J. Org. Chem. 2001, 66, 1009-1013- [3e] Hetero Diels-Alder reactions: D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635-1649. [3f] Molybdenum-catalysed allylic alkylation: F. Glorius, A. Pfaltz, Org. Lett. 1999, 1, 141-144.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 1635-1649
    • Evans, D.A.1    Johnson, J.S.2    Olhava, E.J.3
  • 15
    • 0000199659 scopus 로고    scopus 로고
    • Selected recent references: [3a] Mukaiyama-Michael reactions: D. A. Evans, K. A. Scheidt, J. N. Johnston, M. C. Willis, J. Am. Chem. Soc. 2001, 123, 4480-4491. [3b] Cycloadditions of silyl ketenes: D. A. Evans, J. M. Janey, Org. Lett. 2001, 3, 2125-2128. [3c] Henry reactions: C. Christensen, K. Juhl, K. A. Jorgensen, Chem. Commun. 2001, 2222-2223. [3d] Friedel-Crafts reactions: W. Zhuang, N. Gathergood, R. G. Hazell, K. A. Jorgensen, J. Org. Chem. 2001, 66, 1009-1013- [3e] Hetero Diels-Alder reactions: D. A. Evans, J. S. Johnson, E. J. Olhava, J. Am. Chem. Soc. 2000, 122, 1635-1649. [3f] Molybdenum-catalysed allylic alkylation: F. Glorius, A. Pfaltz, Org. Lett. 1999, 1, 141-144.
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    • Glorius, F.1    Pfaltz, A.2
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    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1848-1849
    • Beller, M.1    Fischer, H.2    Herrmann, W.A.3    Öfele, K.4    Brossner, C.5
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    • Gomez Andreu, M.1    Zapf, A.2    Beller, M.3
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    • For recent reviews of the cross-coupling of organoboron compounds, see: [12a] A. Suzuki, Pure Appl. Chem. 1991, 63, 419-422. [12b] N. Miaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483. [12c] A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168. Selected references: [12d] M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Brossner, Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849. [12e] M. Gomez Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476. [12f] A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 1998, 37, 3387-3388. [12g] J. P. Wolfe, S. L. Buchwald, Angew. Chem. Int. Ed. 1999, 38, 2413-2416. [12h] J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561.
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    • For recent reviews of the cross-coupling of organoboron compounds, see: [12a] A. Suzuki, Pure Appl. Chem. 1991, 63, 419-422. [12b] N. Miaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483. [12c] A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168. Selected references: [12d] M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Brossner, Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849. [12e] M. Gomez Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476. [12f] A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 1998, 37, 3387-3388. [12g] J. P. Wolfe, S. L. Buchwald, Angew. Chem. Int. Ed. 1999, 38, 2413-2416. [12h] J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561.
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    • Wolfe, J.P.1    Singer, R.A.2    Yang, B.H.3    Buchwald, S.L.4


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