Highly active Pd(II) cyclometallated imine catalyst for the Suzuki reaction

Chemical Communications

Volumn , Issue 18, 1999, Pages 1901-1902

  Weissman, Haim ^a   Milstein, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; ORGANOBORON DERIVATIVE; ORGANOHALOGEN DERIVATIVE; PALLADIUM COMPLEX;

ARTICLE; CATALYST; CHEMICAL REACTION;

EID: 0033592451     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906246g     Document Type: Article

References (21)

1. Reviews and very recent references: N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457; A. Suzuki, Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 2, p. 49; A. Suzuki, J. Organomet. Chem., 1999, 576, 147; G. C. Fu and A. F. Littke, Angew. Chem., Int. Ed., 1998, 37, 3387; J. P. Wolfe and S. L. Buchwald, Angew. Chem., Int. Ed., 1999, 38, 2413.
2. Reviews and very recent references: N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457; A. Suzuki, Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 2, p. 49; A. Suzuki, J. Organomet. Chem., 1999, 576, 147; G. C. Fu and A. F. Littke, Angew. Chem., Int. Ed., 1998, 37, 3387; J. P. Wolfe and S. L. Buchwald, Angew. Chem., Int. Ed., 1999, 38, 2413.
3. Reviews and very recent references: N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457; A. Suzuki, Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 2, p. 49; A. Suzuki, J. Organomet. Chem., 1999, 576, 147; G. C. Fu and A. F. Littke, Angew. Chem., Int. Ed., 1998, 37, 3387; J. P. Wolfe and S. L. Buchwald, Angew. Chem., Int. Ed., 1999, 38, 2413.
4. Reviews and very recent references: N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457; A. Suzuki, Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 2, p. 49; A. Suzuki, J. Organomet. Chem., 1999, 576, 147; G. C. Fu and A. F. Littke, Angew. Chem., Int. Ed., 1998, 37, 3387; J. P. Wolfe and S. L. Buchwald, Angew. Chem., Int. Ed., 1999, 38, 2413.
5. Reviews and very recent references: N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457; A. Suzuki, Metal-catalyzed Cross-coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, 1998, ch. 2, p. 49; A. Suzuki, J. Organomet. Chem., 1999, 576, 147; G. C. Fu and A. F. Littke, Angew. Chem., Int. Ed., 1998, 37, 3387; J. P. Wolfe and S. L. Buchwald, Angew. Chem., Int. Ed., 1999, 38, 2413.
6. W. A. Herrmann, C. P. Reisinger and M. Spiegler, J. Organomet. Chem., 1998, 557, 93; C. M. Zhang, J. K. Huang, M. L. Trudell and S. P. Nolan, J. Org. Chem., 1999, 64, 3804; D. S. McGuinness, K. J. Cavell, B. W. Skelton and A. H. White, Organometallics, 1999, 18, 1596; T. I. Wallow and B. M. Novak, J. Org. Chem., 1994, 59, 5034; M. Morenomanas, F. Pajuelo and R. Pleixats, J. Org. Chem., 1995, 60, 2396; M. T. Reetz, R. Breinbauer and K. Wanninger, Tetrahedron Lett., 1996, 37, 4499; N. A. Bumagin and V. V. Byakov, Tetrahedron, 1997, 53, 14437; D. Badone, M. Baroni, R. Cardamone, A. Ielmini and U. Guzzi, J. Org. Chem., 1997, 62, 7170; C. G. Blettner, W. A. Konig, W. Stenzel and T. Schotten, J. Org. Chem., 1999, 64, 3885.
7. W. A. Herrmann, C. P. Reisinger and M. Spiegler, J. Organomet. Chem., 1998, 557, 93; C. M. Zhang, J. K. Huang, M. L. Trudell and S. P. Nolan, J. Org. Chem., 1999, 64, 3804; D. S. McGuinness, K. J. Cavell, B. W. Skelton and A. H. White, Organometallics, 1999, 18, 1596; T. I. Wallow and B. M. Novak, J. Org. Chem., 1994, 59, 5034; M. Morenomanas, F. Pajuelo and R. Pleixats, J. Org. Chem., 1995, 60, 2396; M. T. Reetz, R. Breinbauer and K. Wanninger, Tetrahedron Lett., 1996, 37, 4499; N. A. Bumagin and V. V. Byakov, Tetrahedron, 1997, 53, 14437; D. Badone, M. Baroni, R. Cardamone, A. Ielmini and U. Guzzi, J. Org. Chem., 1997, 62, 7170; C. G. Blettner, W. A. Konig, W. Stenzel and T. Schotten, J. Org. Chem., 1999, 64, 3885.
8. W. A. Herrmann, C. P. Reisinger and M. Spiegler, J. Organomet. Chem., 1998, 557, 93; C. M. Zhang, J. K. Huang, M. L. Trudell and S. P. Nolan, J. Org. Chem., 1999, 64, 3804; D. S. McGuinness, K. J. Cavell, B. W. Skelton and A. H. White, Organometallics, 1999, 18, 1596; T. I. Wallow and B. M. Novak, J. Org. Chem., 1994, 59, 5034; M. Morenomanas, F. Pajuelo and R. Pleixats, J. Org. Chem., 1995, 60, 2396; M. T. Reetz, R. Breinbauer and K. Wanninger, Tetrahedron Lett., 1996, 37, 4499; N. A. Bumagin and V. V. Byakov, Tetrahedron, 1997, 53, 14437; D. Badone, M. Baroni, R. Cardamone, A. Ielmini and U. Guzzi, J. Org. Chem., 1997, 62, 7170; C. G. Blettner, W. A. Konig, W. Stenzel and T. Schotten, J. Org. Chem., 1999, 64, 3885.
9. W. A. Herrmann, C. P. Reisinger and M. Spiegler, J. Organomet. Chem., 1998, 557, 93; C. M. Zhang, J. K. Huang, M. L. Trudell and S. P. Nolan, J. Org. Chem., 1999, 64, 3804; D. S. McGuinness, K. J. Cavell, B. W. Skelton and A. H. White, Organometallics, 1999, 18, 1596; T. I. Wallow and B. M. Novak, J. Org. Chem., 1994, 59, 5034; M. Morenomanas, F. Pajuelo and R. Pleixats, J. Org. Chem., 1995, 60, 2396; M. T. Reetz, R. Breinbauer and K. Wanninger, Tetrahedron Lett., 1996, 37, 4499; N. A. Bumagin and V. V. Byakov, Tetrahedron, 1997, 53, 14437; D. Badone, M. Baroni, R. Cardamone, A. Ielmini and U. Guzzi, J. Org. Chem., 1997, 62, 7170; C. G. Blettner, W. A. Konig, W. Stenzel and T. Schotten, J. Org. Chem., 1999, 64, 3885.
10. W. A. Herrmann, C. P. Reisinger and M. Spiegler, J. Organomet. Chem., 1998, 557, 93; C. M. Zhang, J. K. Huang, M. L. Trudell and S. P. Nolan, J. Org. Chem., 1999, 64, 3804; D. S. McGuinness, K. J. Cavell, B. W. Skelton and A. H. White, Organometallics, 1999, 18, 1596; T. I. Wallow and B. M. Novak, J. Org. Chem., 1994, 59, 5034; M. Morenomanas, F. Pajuelo and R. Pleixats, J. Org. Chem., 1995, 60, 2396; M. T. Reetz, R. Breinbauer and K. Wanninger, Tetrahedron Lett., 1996, 37, 4499; N. A. Bumagin and V. V. Byakov, Tetrahedron, 1997, 53, 14437; D. Badone, M. Baroni, R. Cardamone, A. Ielmini and U. Guzzi, J. Org. Chem., 1997, 62, 7170; C. G. Blettner, W. A. Konig, W. Stenzel and T. Schotten, J. Org. Chem., 1999, 64, 3885.
11. W. A. Herrmann, C. P. Reisinger and M. Spiegler, J. Organomet. Chem., 1998, 557, 93; C. M. Zhang, J. K. Huang, M. L. Trudell and S. P. Nolan, J. Org. Chem., 1999, 64, 3804; D. S. McGuinness, K. J. Cavell, B. W. Skelton and A. H. White, Organometallics, 1999, 18, 1596; T. I. Wallow and B. M. Novak, J. Org. Chem., 1994, 59, 5034; M. Morenomanas, F. Pajuelo and R. Pleixats, J. Org. Chem., 1995, 60, 2396; M. T. Reetz, R. Breinbauer and K. Wanninger, Tetrahedron Lett., 1996, 37, 4499; N. A. Bumagin and V. V. Byakov, Tetrahedron, 1997, 53, 14437; D. Badone, M. Baroni, R. Cardamone, A. Ielmini and U. Guzzi, J. Org. Chem., 1997, 62, 7170; C. G. Blettner, W. A. Konig, W. Stenzel and T. Schotten, J. Org. Chem., 1999, 64, 3885.
12. W. A. Herrmann, C. P. Reisinger and M. Spiegler, J. Organomet. Chem., 1998, 557, 93; C. M. Zhang, J. K. Huang, M. L. Trudell and S. P. Nolan, J. Org. Chem., 1999, 64, 3804; D. S. McGuinness, K. J. Cavell, B. W. Skelton and A. H. White, Organometallics, 1999, 18, 1596; T. I. Wallow and B. M. Novak, J. Org. Chem., 1994, 59, 5034; M. Morenomanas, F. Pajuelo and R. Pleixats, J. Org. Chem., 1995, 60, 2396; M. T. Reetz, R. Breinbauer and K. Wanninger, Tetrahedron Lett., 1996, 37, 4499; N. A. Bumagin and V. V. Byakov, Tetrahedron, 1997, 53, 14437; D. Badone, M. Baroni, R. Cardamone, A. Ielmini and U. Guzzi, J. Org. Chem., 1997, 62, 7170; C. G. Blettner, W. A. Konig, W. Stenzel and T. Schotten, J. Org. Chem., 1999, 64, 3885.
13. W. A. Herrmann, C. P. Reisinger and M. Spiegler, J. Organomet. Chem., 1998, 557, 93; C. M. Zhang, J. K. Huang, M. L. Trudell and S. P. Nolan, J. Org. Chem., 1999, 64, 3804; D. S. McGuinness, K. J. Cavell, B. W. Skelton and A. H. White, Organometallics, 1999, 18, 1596; T. I. Wallow and B. M. Novak, J. Org. Chem., 1994, 59, 5034; M. Morenomanas, F. Pajuelo and R. Pleixats, J. Org. Chem., 1995, 60, 2396; M. T. Reetz, R. Breinbauer and K. Wanninger, Tetrahedron Lett., 1996, 37, 4499; N. A. Bumagin and V. V. Byakov, Tetrahedron, 1997, 53, 14437; D. Badone, M. Baroni, R. Cardamone, A. Ielmini and U. Guzzi, J. Org. Chem., 1997, 62, 7170; C. G. Blettner, W. A. Konig, W. Stenzel and T. Schotten, J. Org. Chem., 1999, 64, 3885.
14. W. A. Herrmann, C. P. Reisinger and M. Spiegler, J. Organomet. Chem., 1998, 557, 93; C. M. Zhang, J. K. Huang, M. L. Trudell and S. P. Nolan, J. Org. Chem., 1999, 64, 3804; D. S. McGuinness, K. J. Cavell, B. W. Skelton and A. H. White, Organometallics, 1999, 18, 1596; T. I. Wallow and B. M. Novak, J. Org. Chem., 1994, 59, 5034; M. Morenomanas, F. Pajuelo and R. Pleixats, J. Org. Chem., 1995, 60, 2396; M. T. Reetz, R. Breinbauer and K. Wanninger, Tetrahedron Lett., 1996, 37, 4499; N. A. Bumagin and V. V. Byakov, Tetrahedron, 1997, 53, 14437; D. Badone, M. Baroni, R. Cardamone, A. Ielmini and U. Guzzi, J. Org. Chem., 1997, 62, 7170; C. G. Blettner, W. A. Konig, W. Stenzel and T. Schotten, J. Org. Chem., 1999, 64, 3885.
15. M. Beller, H. Fischer, W. A. Herrmann, K. Öfele and C. Brossmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 1848; D. A. Albisson, R. B. Bedford, S. E. Lawrence and P. N. Scully, Chem. Commun., 1998, 2095; W. A. Herrmann and V. P. W. Böhm, J. Organomet. Chem., 1999, 572, 141.
16. M. Beller, H. Fischer, W. A. Herrmann, K. Öfele and C. Brossmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 1848; D. A. Albisson, R. B. Bedford, S. E. Lawrence and P. N. Scully, Chem. Commun., 1998, 2095; W. A. Herrmann and V. P. W. Böhm, J. Organomet. Chem., 1999, 572, 141.
17. M. Beller, H. Fischer, W. A. Herrmann, K. Öfele and C. Brossmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 1848; D. A. Albisson, R. B. Bedford, S. E. Lawrence and P. N. Scully, Chem. Commun., 1998, 2095; W. A. Herrmann and V. P. W. Böhm, J. Organomet. Chem., 1999, 572, 141.
18. M. Ohff, A. Ohff, M. E. van der Boom and D. Milstein, J. Am. Chem. Soc., 1997, 119, 11687.
19. M. Ohff, A. Ohff and D. Milstein, Israel Patent Appl. 121346 (filed on 20.07.1997); M. Ohff, A. Ohff and D. Milstein, Chem. Commun., 1999, 357.
20. M. Ohff, A. Ohff and D. Milstein, Israel Patent Appl. 121346 (filed on 20.07.1997); M. Ohff, A. Ohff and D. Milstein, Chem. Commun., 1999, 357.
21. M. Portnoy and D. Milstein, Organometallics, 1993, 12, 1665.