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Volumn 343, Issue 4, 2001, Pages 338-342

Palladacycles as Precatalysts in Heck and Cross-Coupling Reactions

Author keywords

Cross coupling; Heck reaction; Homogeneous catalysis; Metallacycles; P ligands; Palladium

Indexed keywords


EID: 0141847465     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(20010226)343:4<338::aid-adsc338>3.0.co;2-i     Document Type: Article
Times cited : (52)

References (70)
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    • Palladium complexes with heterocyclic carbenes as the ligands also show excellent reactivity: (a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. Int. Ed. Engl. 1993, 34, 2371; (b) W. A. Herrmann, C.-P. Reisinger, M. Spiegler, J. Organomet. Chem. 1998, 557, 93; (c) T. Weskamp, V. P. W. Böhm, W. A. Herrmann, J. Organomet. Chem. 1999, 585, 348; C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804; (e) C. Zhang, M. L. Trudell, Tetrahedron Lett. 2000, 41, 595; (f) See also: A. J. Carmichael, M. J. Earle, J. D. Holbrey, P. B. McCormac, K. R. Seddon, Org. Lett. 1999, 1, 997.
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    • Palladium complexes with heterocyclic carbenes as the ligands also show excellent reactivity: (a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. Int. Ed. Engl. 1993, 34, 2371; (b) W. A. Herrmann, C.-P. Reisinger, M. Spiegler, J. Organomet. Chem. 1998, 557, 93; T. Weskamp, V. P. W. Böhm, W. A. Herrmann, J. Organomet. Chem. 1999, 585, 348; (d) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804; (e) C. Zhang, M. L. Trudell, Tetrahedron Lett. 2000, 41, 595; (f) See also: A. J. Carmichael, M. J. Earle, J. D. Holbrey, P. B. McCormac, K. R. Seddon, Org. Lett. 1999, 1, 997.
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    • Palladium complexes with heterocyclic carbenes as the ligands also show excellent reactivity: (a) W. A. Herrmann, M. Elison, J. Fischer, C. Köcher, G. R. J. Artus, Angew. Chem. Int. Ed. Engl. 1993, 34, 2371; (b) W. A. Herrmann, C.-P. Reisinger, M. Spiegler, J. Organomet. Chem. 1998, 557, 93; T. Weskamp, V. P. W. Böhm, W. A. Herrmann, J. Organomet. Chem. 1999, 585, 348; C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804; (e) C. Zhang, M. L. Trudell, Tetrahedron Lett. 2000, 41, 595; (f) See also: A. J. Carmichael, M. J. Earle, J. D. Holbrey, P. B. McCormac, K. R. Seddon, Org. Lett. 1999, 1, 997.
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    • For related phospha-palladacycles: (a) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; (b) M. Spescha, B. L. Shaw, S. D. Perera, E. A. Staley, Chem. Commun. 1998, 1361; K. Kiewel, Y. Liu, D. E. Bergbreiter, G. A. Sulikowski, Tetrahedron Lett. 1999, 40, 8945; I. P. Beletskaya, A. V. Chuchurjukin, H. P. Dijkstra, G. P. M. Van Klink, G. van Koten, Tetrahedron Lett. 2000, 41, 1075.
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    • For related phospha-palladacycles: (a) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; (b) M. Spescha, B. L. Shaw, S. D. Perera, E. A. Staley, Chem. Commun. 1998, 1361; K. Kiewel, Y. Liu, D. E. Bergbreiter, G. A. Sulikowski, Tetrahedron Lett. 1999, 40, 8945; I. P. Beletskaya, A. V. Chuchurjukin, H. P. Dijkstra, G. P. M. Van Klink, G. van Koten, Tetrahedron Lett. 2000, 41, 1075.
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    • For related phospha-palladacycles: (a) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; (b) M. Spescha, B. L. Shaw, S. D. Perera, E. A. Staley, Chem. Commun. 1998, 1361; (c) K. Kiewel, Y. Liu, D. E. Bergbreiter, G. A. Sulikowski, Tetrahedron Lett. 1999, 40, 8945; I. P. Beletskaya, A. V. Chuchurjukin, H. P. Dijkstra, G. P. M. Van Klink, G. van Koten, Tetrahedron Lett. 2000, 41, 1075.
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    • For related phospha-palladacycles: (a) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; (b) M. Spescha, B. L. Shaw, S. D. Perera, E. A. Staley, Chem. Commun. 1998, 1361; K. Kiewel, Y. Liu, D. E. Bergbreiter, G. A. Sulikowski, Tetrahedron Lett. 1999, 40, 8945; (d) I. P. Beletskaya, A. V. Chuchurjukin, H. P. Dijkstra, G. P. M. Van Klink, G. van Koten, Tetrahedron Lett. 2000, 41, 1075.
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    • Turnover number = mol product/mol Pd.
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    • Oxidative addition of aryl halides to Pt(II) only proceeds intramolecularly: C. R. Baar, G. S. Hill, J. J. Vittal, R. J. Puddephatt, Organometallics 1998, 17, 32, and references cited therein.
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    • 2Cl] oxidatively adds MeI at 23°C (see: R. J. Mureinik, M. Weizberg, J. Blum, J. Inorg. Chem. 1979, 18, 915; J. Blum, M. Weizberg, R. J. Mureinik, J. Organomet. Chem. 1976, 122, 261), the reaction with aryl iodides occurs only under forcing conditions: P. B. Chock, J, Halpern, J. Am. Chem. Soc. 1966, 88, 3511.
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    • 2Cl] oxidatively adds MeI at 23°C (see: R. J. Mureinik, M. Weizberg, J. Blum, J. Inorg. Chem. 1979, 18, 915; J. Blum, M. Weizberg, R. J. Mureinik, J. Organomet. Chem. 1976, 122, 261), the reaction with aryl iodides occurs only under forcing conditions: P. B. Chock, J, Halpern, J. Am. Chem. Soc. 1966, 88, 3511.
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    • Blum, J.1    Weizberg, M.2    Mureinik, R.J.3
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    • 2Cl] oxidatively adds MeI at 23°C (see: R. J. Mureinik, M. Weizberg, J. Blum, J. Inorg. Chem. 1979, 18, 915; J. Blum, M. Weizberg, R. J. Mureinik, J. Organomet. Chem. 1976, 122, 261), the reaction with aryl iodides occurs only under forcing conditions: P. B. Chock, J, Halpern, J. Am. Chem. Soc. 1966, 88, 3511.
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    • For the destabilization introduced by the non-bonding interaction between filled orbitals on the metal and on the oxygen, see: (a) H. E. Bryndza, W. Tam. Chem. Rev. 1988, 88, 1163; (b) M. D. Fryzuk, C. D. Montgomery, Coord. Chem. Rev. 1989, 95, 1; R. C. Mehrotra, S. K. Agarwal, Y. P. Singh, Coord. Chem. Rev. 1985, 68, 101; J. C. M. Ritter, R. G. Bergman, J. Am. Chem. Soc. 1998, 120, 6826.
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    • For the destabilization introduced by the non-bonding interaction between filled orbitals on the metal and on the oxygen, see: (a) H. E. Bryndza, W. Tam. Chem. Rev. 1988, 88, 1163; (b) M. D. Fryzuk, C. D. Montgomery, Coord. Chem. Rev. 1989, 95, 1; (c) R. C. Mehrotra, S. K. Agarwal, Y. P. Singh, Coord. Chem. Rev. 1985, 68, 101; J. C. M. Ritter, R. G. Bergman, J. Am. Chem. Soc. 1998, 120, 6826.
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    • For the destabilization introduced by the non-bonding interaction between filled orbitals on the metal and on the oxygen, see: (a) H. E. Bryndza, W. Tam. Chem. Rev. 1988, 88, 1163; (b) M. D. Fryzuk, C. D. Montgomery, Coord. Chem. Rev. 1989, 95, 1; R. C. Mehrotra, S. K. Agarwal, Y. P. Singh, Coord. Chem. Rev. 1985, 68, 101; (d) J. C. M. Ritter, R. G. Bergman, J. Am. Chem. Soc. 1998, 120, 6826.
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    • Ritter, J.C.M.1    Bergman, R.G.2
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    • note
    • 2 also catalyzed the formation of 23 from 12 (92% yield, 16 h, 130°C).
  • 63
    • 0347628526 scopus 로고    scopus 로고
    • note
    • The black solutions could be filtered through Celite under Ar without a loss in their catalytic activity.
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    • 85087227228 scopus 로고    scopus 로고
    • note
    • [19] were also unreactive towards iodobenzene or arylbromides bearing electron-withdrawing groups at the para position.
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    • note
    • [1d]
  • 69
    • 0346367843 scopus 로고    scopus 로고
    • The Aldrich Library of FT-NMR Spectra
    • The Aldrich Library of FT-NMR Spectra.


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