A highly active catalyst for the room-temperature amination and Suzuki coupling of aryl chlorides

Angewandte Chemie - International Edition

Volumn 38, Issue 16, 1999, Pages 2413-2416

  Wolfe, John P ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Aminations; Biaryls; Catalysts; Ligand effects; Palladium

Indexed keywords

PALLADIUM;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; STEREOSPECIFICITY; TEMPERATURE SENSITIVITY;

EID: 0033549829     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990816)38:16<2413::AID-ANIE2413>3.0.CO;2-H     Document Type: Article

References (44)

1. a) J. P. Wolfe, S. Wagaw, J.-F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805-818;
2. b) J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
3. b) J. F. Hartwig, Angew. Chem. 1998, 110, 2154-2177; Angew. Chem. Int. Ed. 1998, 37, 2046-2067;
4. c) B. H. Yang, S. L. Buchwald, J. Organomet. Chem. 1999, 576, 125-146.
5. A. Suzuki in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), WILEY-VCH, Weinheim, 1998, chap. 2.
6. V. V. Grushin, H. Alper, Chem. Rev. 1994, 94, 1047-1062.
7. a) The Herrmann/Beller palladacycle catalyst has been demonstrated to be effective for some C-C and C-N bond forming reactions of aryl chlorides at 135°C: T. H. Riermeier, A. Zapf, M. Beller, Top. Catal. 1997, 4, 301-309, and references therein.
8. b) Herrmann has demonstrated the Suzuki coupling of 4-chloroacetophenone using palladium complexes bearing chelating, heterocyclic carbene ligands: W. A. Herrmann, C.-P. Reisinger, M. Spiegler, J. Organomet. Chem. 1998, 557, 93-96.
9. c) Trudell, Nolan et al. have recently reported the Suzuki coupling of aryl chlorides using bulky, heterocyclic carbene ligands: C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805.
10. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
11. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
12. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
13. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
14. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
15. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
16. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
17. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
18. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
19. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
20. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
21. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
22. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
23. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
24. 3 as the supporting ligand: A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388; n) X. Bei, T. Crevier, A. S. Guram, B. Jandeleit, T. S. Powers, H. W. Turner, T. Uno, W. H. Weinberg, Tetrahedron Lett. 1999, 40, 3855-3858.
25. D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723.
26. The few previously reported methods for room-temperature Suzuki couplings frequently require toxic additives and do not function for aryl chloride substrates: J. C. Anderson, H. Namli, C. A. Roberts, Tetrahedron 1997, 53, 15123-15134, and references therein.
27. Bulky ligands have been shown to accelerate other palladium-catalyzed cross-coupling reactions: a) V. Farina in Comprehensive Organometallic Chemistry, Vol. 12, 2nd ed., Pergamon, Oxford, 1995, pp. 161-240; b) J. F. Hartwig, S. Richards, D. Baranano, F. Paul, J. Am. Chem. Soc. 1996, 118, 3626-3633.
28. Bulky ligands have been shown to accelerate other palladium-catalyzed cross-coupling reactions: a) V. Farina in Comprehensive Organometallic Chemistry, Vol. 12, 2nd ed., Pergamon, Oxford, 1995, pp. 161-240; b) J. F. Hartwig, S. Richards, D. Baranano, F. Paul, J. Am. Chem. Soc. 1996, 118, 3626-3633.
29. Ligands 3 and 4 are air-stable, crystalline solids which are prepared in one step. These ligands are now commercially available from Strem Chemical Co.
30. 4 in place of NaOtBu at 80-100°C. These results will be reported in full papers.
31. The scope and limitations of Suzuki couplings which employ 3 or 4 will be the subject of a full paper.
32. All reactions proceed to completion unless otherwise noted.
33. 6, respectively, for this reaction: a) M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Brossmer, Angew. Chem. 1995, 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849; b) D. A. Albisson, R. B. Bedford, S. E. Lawrence, P. N. Scully, Chem. Commun. 1998, 2095-2096.
34. 6, respectively, for this reaction: a) M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Brossmer, Angew. Chem. 1995, 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849; b) D. A. Albisson, R. B. Bedford, S. E. Lawrence, P. N. Scully, Chem. Commun. 1998, 2095-2096.
35. 6, respectively, for this reaction: a) M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Brossmer, Angew. Chem. 1995, 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 34, 1848-1849; b) D. A. Albisson, R. B. Bedford, S. E. Lawrence, P. N. Scully, Chem. Commun. 1998, 2095-2096.
36. Under these conditions, Suzuki coupling reactions of other substrates give little or no products in the absence of phosphane ligands.
37. a) G. O. Spessard, G. L. Meissler, Organometallic Chemistry, Prentice-Hall, Upper Saddle River, NJ, 1996, pp. 171-175;
38. b) M. Portnoy, D. Milstein, Organometallics 1993, 12, 1665-1673.
39. Metal-π interactions have been observed in other palladium complexes: a) H. Ossor, M. Pfeffer, J. T. B. H. Jastrzebski, C. H. Stam, Inorg. Chem. 1987, 26, 1169-1171; b) L. R. Falvello, J. Fornies, R. Navarro, V. Sicilia, M. Tomas, Angew. Chem. 1990, 102, 952-954; Angew. Chem. Int. Ed. Engl. 1990, 29, 891-893; c) C.-S. Li, C.-H. Cheng, F.-L. Liao, S.-L. Wang, J. Chem. Soc. Chem. Commun. 1991, 710-711; d) S. Kannan, A. J. James, P. R. Sharp, J. Am. Chem. Soc. 1998, 120, 215-216.
40. Metal-π interactions have been observed in other palladium complexes: a) H. Ossor, M. Pfeffer, J. T. B. H. Jastrzebski, C. H. Stam, Inorg. Chem. 1987, 26, 1169-1171; b) L. R. Falvello, J. Fornies, R. Navarro, V. Sicilia, M. Tomas, Angew. Chem. 1990, 102, 952-954; Angew. Chem. Int. Ed. Engl. 1990, 29, 891-893; c) C.-S. Li, C.-H. Cheng, F.-L. Liao, S.-L. Wang, J. Chem. Soc. Chem. Commun. 1991, 710-711; d) S. Kannan, A. J. James, P. R. Sharp, J. Am. Chem. Soc. 1998, 120, 215-216.
41. Metal-π interactions have been observed in other palladium complexes: a) H. Ossor, M. Pfeffer, J. T. B. H. Jastrzebski, C. H. Stam, Inorg. Chem. 1987, 26, 1169-1171; b) L. R. Falvello, J. Fornies, R. Navarro, V. Sicilia, M. Tomas, Angew. Chem. 1990, 102, 952-954; Angew. Chem. Int. Ed. Engl. 1990, 29, 891-893; c) C.-S. Li, C.-H. Cheng, F.-L. Liao, S.-L. Wang, J. Chem. Soc. Chem. Commun. 1991, 710-711; d) S. Kannan, A. J. James, P. R. Sharp, J. Am. Chem. Soc. 1998, 120, 215-216.
42. Metal-π interactions have been observed in other palladium complexes: a) H. Ossor, M. Pfeffer, J. T. B. H. Jastrzebski, C. H. Stam, Inorg. Chem. 1987, 26, 1169-1171; b) L. R. Falvello, J. Fornies, R. Navarro, V. Sicilia, M. Tomas, Angew. Chem. 1990, 102, 952-954; Angew. Chem. Int. Ed. Engl. 1990, 29, 891-893; c) C.-S. Li, C.-H. Cheng, F.-L. Liao, S.-L. Wang, J. Chem. Soc. Chem. Commun. 1991, 710-711; d) S. Kannan, A. J. James, P. R. Sharp, J. Am. Chem. Soc. 1998, 120, 215-216.
43. Metal-π interactions have been observed in other palladium complexes: a) H. Ossor, M. Pfeffer, J. T. B. H. Jastrzebski, C. H. Stam, Inorg. Chem. 1987, 26, 1169-1171; b) L. R. Falvello, J. Fornies, R. Navarro, V. Sicilia, M. Tomas, Angew. Chem. 1990, 102, 952-954; Angew. Chem. Int. Ed. Engl. 1990, 29, 891-893; c) C.-S. Li, C.-H. Cheng, F.-L. Liao, S.-L. Wang, J. Chem. Soc. Chem. Commun. 1991, 710-711; d) S. Kannan, A. J. James, P. R. Sharp, J. Am. Chem. Soc. 1998, 120, 215-216.
44. II has been postulated to occur via a transition state in which both aryl groups are perpendicular to the coordination plane: P. S. Braterman, R. J. Cross, G. B. Young, J. Chem. Soc. Dalton Trans. 1 1977, 1892-1897.