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Volumn 24, Issue 6, 2005, Pages 1075-1081

Air- and moisture-stable cyclopalladated complexes as efficient catalysts for Suzuki-Miyaura coupling reaction

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHELATION; CHEMICAL REACTIONS; CRYSTAL STRUCTURE; ETHANOL; NUCLEAR MAGNETIC RESONANCE; ORGANIC ACIDS; ORGANOMETALLICS; SOLUTIONS; SUBSTRATES; SYNTHESIS (CHEMICAL);

EID: 15944427092     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om049125t     Document Type: Article
Times cited : (87)

References (56)
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    • Recent reviews: (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (B) Stanforth, S. P. Tetrahedron 1998, 54, 263. (c) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (d) Bedford, R. B. Chem. Commun. 2003, 1787. (e) Tucker, C. E.; De Vries, J. G. Top. Catal. 2002, 19, 111. (f) Singleton, J. T. Tetrahedron 2003, 59, 1837. (g) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695. (h) Marshall, J. A. Chemtracts 2000, 13, 219. (i) Kocovsky, P.; Malkov, A. V.; Vyskocil, S.; Lloyd-Jones, G. C. Pure Appl. Chem. 1999, 71, 1425-1433. (j) Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; 2002; Vol. 1, 591 pp.
    • (2002) Tetrahedron , vol.58 , pp. 9633-9695
    • Kotha, S.1    Lahiri, K.2    Kashinath, D.3
  • 8
    • 0033935206 scopus 로고    scopus 로고
    • Recent reviews: (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (B) Stanforth, S. P. Tetrahedron 1998, 54, 263. (c) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (d) Bedford, R. B. Chem. Commun. 2003, 1787. (e) Tucker, C. E.; De Vries, J. G. Top. Catal. 2002, 19, 111. (f) Singleton, J. T. Tetrahedron 2003, 59, 1837. (g) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695. (h) Marshall, J. A. Chemtracts 2000, 13, 219. (i) Kocovsky, P.; Malkov, A. V.; Vyskocil, S.; Lloyd-Jones, G. C. Pure Appl. Chem. 1999, 71, 1425-1433. (j) Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; 2002; Vol. 1, 591 pp.
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  • 9
    • 0345614216 scopus 로고    scopus 로고
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  • 10
    • 15944370056 scopus 로고    scopus 로고
    • Recent reviews: (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147. (B) Stanforth, S. P. Tetrahedron 1998, 54, 263. (c) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. (d) Bedford, R. B. Chem. Commun. 2003, 1787. (e) Tucker, C. E.; De Vries, J. G. Top. Catal. 2002, 19, 111. (f) Singleton, J. T. Tetrahedron 2003, 59, 1837. (g) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633-9695. (h) Marshall, J. A. Chemtracts 2000, 13, 219. (i) Kocovsky, P.; Malkov, A. V.; Vyskocil, S.; Lloyd-Jones, G. C. Pure Appl. Chem. 1999, 71, 1425-1433. (j) Herrmann, W. A. Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; 2002; Vol. 1, 591 pp.
    • (2002) Applied Homogeneous Catalysis with Organometallic Compounds, 2nd Ed. , vol.1
    • Herrmann, W.A.1
  • 22
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    • Aryl chlorides as substrates for Suzuki couplings; see: (a) Li, G. Y. J. Org. Chem. 2002, 67, 3643. (b) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295. (d) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (f) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P J. Org. Chem. 1999, 64, 3804. (h) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194. (i) Navarro, O.; Oonishi, Y.; Kelly, R. A.; Stevens, E. D.; Briel, O.; Nolan, S. P. J. Organomet. Chem. 2004, 689, 3722, and references therein.
    • (2002) J. Org. Chem. , vol.67 , pp. 3643
    • Li, G.Y.1
  • 23
    • 0035824304 scopus 로고    scopus 로고
    • Aryl chlorides as substrates for Suzuki couplings; see: (a) Li, G. Y. J. Org. Chem. 2002, 67, 3643. (b) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295. (d) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (f) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P J. Org. Chem. 1999, 64, 3804. (h) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194. (i) Navarro, O.; Oonishi, Y.; Kelly, R. A.; Stevens, E. D.; Briel, O.; Nolan, S. P. J. Organomet. Chem. 2004, 689, 3722, and references therein.
    • (2001) Chem. Commun. , pp. 2408
    • Liu, S.-Y.1    Choi, M.J.2    Fu, G.C.3
  • 24
    • 0035961019 scopus 로고    scopus 로고
    • Aryl chlorides as substrates for Suzuki couplings; see: (a) Li, G. Y. J. Org. Chem. 2002, 67, 3643. (b) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295. (d) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (f) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P J. Org. Chem. 1999, 64, 3804. (h) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194. (i) Navarro, O.; Oonishi, Y.; Kelly, R. A.; Stevens, E. D.; Briel, O.; Nolan, S. P. J. Organomet. Chem. 2004, 689, 3722, and references therein.
    • (2001) Org. Lett. , vol.3 , pp. 4295
    • Netherton, M.R.1    Fu, G.C.2
  • 25
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    • Aryl chlorides as substrates for Suzuki couplings; see: (a) Li, G. Y. J. Org. Chem. 2002, 67, 3643. (b) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295. (d) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (f) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P J. Org. Chem. 1999, 64, 3804. (h) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194. (i) Navarro, O.; Oonishi, Y.; Kelly, R. A.; Stevens, E. D.; Briel, O.; Nolan, S. P. J. Organomet. Chem. 2004, 689, 3722, and references therein.
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    • Zapf, A.1    Ehrentraut, A.2    Beller, M.3
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    • Aryl chlorides as substrates for Suzuki couplings; see: (a) Li, G. Y. J. Org. Chem. 2002, 67, 3643. (b) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295. (d) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (f) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P J. Org. Chem. 1999, 64, 3804. (h) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194. (i) Navarro, O.; Oonishi, Y.; Kelly, R. A.; Stevens, E. D.; Briel, O.; Nolan, S. P. J. Organomet. Chem. 2004, 689, 3722, and references therein.
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    • Aryl chlorides as substrates for Suzuki couplings; see: (a) Li, G. Y. J. Org. Chem. 2002, 67, 3643. (b) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295. (d) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (f) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P J. Org. Chem. 1999, 64, 3804. (h) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194. (i) Navarro, O.; Oonishi, Y.; Kelly, R. A.; Stevens, E. D.; Briel, O.; Nolan, S. P. J. Organomet. Chem. 2004, 689, 3722, and references therein.
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    • Bei, X.1    Turner, H.W.2    Weinberg, W.H.3    Guram, A.S.4
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    • Aryl chlorides as substrates for Suzuki couplings; see: (a) Li, G. Y. J. Org. Chem. 2002, 67, 3643. (b) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295. (d) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (f) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P J. Org. Chem. 1999, 64, 3804. (h) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194. (i) Navarro, O.; Oonishi, Y.; Kelly, R. A.; Stevens, E. D.; Briel, O.; Nolan, S. P. J. Organomet. Chem. 2004, 689, 3722, and references therein.
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    • Zhang, C.1    Huang, J.2    Trudell, M.L.3    Nolan, S.P.4
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    • Aryl chlorides as substrates for Suzuki couplings; see: (a) Li, G. Y. J. Org. Chem. 2002, 67, 3643. (b) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295. (d) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (f) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P J. Org. Chem. 1999, 64, 3804. (h) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194. (i) Navarro, O.; Oonishi, Y.; Kelly, R. A.; Stevens, E. D.; Briel, O.; Nolan, S. P. J. Organomet. Chem. 2004, 689, 3722, and references therein.
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    • Aryl chlorides as substrates for Suzuki couplings; see: (a) Li, G. Y. J. Org. Chem. 2002, 67, 3643. (b) Liu, S.-Y.; Choi, M. J.; Fu, G. C. Chem. Commun. 2001, 2408. (c) Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295. (d) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. (f) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797. (g) Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P J. Org. Chem. 1999, 64, 3804. (h) Navarro, O.; Kelly, R. A.; Nolan, S. P. J. Am. Chem. Soc. 2003, 125, 16194. (i) Navarro, O.; Oonishi, Y.; Kelly, R. A.; Stevens, E. D.; Briel, O.; Nolan, S. P. J. Organomet. Chem. 2004, 689, 3722, and references therein.
    • (2004) J. Organomet. Chem. , vol.689 , pp. 3722
    • Navarro, O.1    Oonishi, Y.2    Kelly, R.A.3    Stevens, E.D.4    Briel, O.5    Nolan, S.P.6


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