Simple mixed tricyclohexylphosphane-triarylphosphite complexes as extremely high-activity catalysts for the Suzuki coupling of aryl chlorides

Angewandte Chemie - International Edition

Volumn 41, Issue 21, 2002, Pages 4120-4122

  Bedford, Robin B ^a   Cazin, Catherine S J ^a   Hazelwood, Samantha L ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

C C coupling; Homogeneous catalysis; Palladium; Suzuki reaction

Indexed keywords

ADDITION REACTIONS; CATALYSTS; SUBSTRATES;

COUPLING REACTIONS;

CHEMICAL ANALYSIS;

CHLORIDE; PHOSPHITE; PHOSPHORUS DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TRICYCLOHEXYLPHOSPHANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; MOLECULAR STABILITY; REACTION ANALYSIS; SYNTHESIS;

EID: 0037021074     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021104)41:21<4120::AID-ANIE4120>3.0.CO;2-7     Document Type: Article

References (24)

1. a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483
2. b) S. P. Stanforth, Tetrahedron 1998, 54. 263-303
3. c) A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168.
4. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
5. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
6. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
7. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
8. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
9. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
10. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
11. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
12. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
13. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
14. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
15. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
16. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
17. Recent examples of Suzuki coupling reactions with aryl chlorides: a) L. Botella. C. Nájera, Angew. Chem, 2002, 114, 187-189; Angew. Chem. Int. Ed. 2002, 41, 179-181; b) S.-Y. Liu. M. J. Choi, G. C. Fu, Chem. Commun. 2001, 2408-2409; c) R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2001, 1540-1541; d) M. R. Netherton, G. C. Fu, Org. Lett. 2001, 3, 4295-4298; e) A. Zapf, A. Ehrentraut, M. Beller, Angew. Chem. 2000, 112, 4315-4317; Angew. Chem. Int. Ed. 2000, 39, 4153-4155; f) M. G. Andreu, A. Zapf, M. Beller, Chem. Commun. 2000, 2475-2476; g) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723; h) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc, 1999, 121, 9550-9561; i) X. Bei, H. W. Turner, W. H. Weinberg, A. S. Guram, J. Org. Chem. 1999, 64, 6797-6803; j) C. Zhang, J. Huang, M. L. Trudell, S. P. Nolan, J. Org. Chem. 1999, 64, 3804-3805; k) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586-3587; Angew. Chem. Int. Ed. 1998, 37, 3387-3388.
18. Ligand 3 is cheaper than triphenylphosphane (source: Aldrich Chemicals catalogue).
19. D. A. Albisson, R. B, Bedford, S. E. Lawrence, P. N. Scully, Chem. Commun. 1998, 2095-2096.
20. R. B. Bedford, S. L. Welch, Chem. Commmun. 2001, 129-130.
21. P.P=40 Hz).
22. Fu and co-workers have recently reported that highly sterically hindered triarylphosphanes can catalyze couplings of electronically deactivated aryl chlorides (see ref. [2b]), indicating that more subtle effects than brute donor-strength can play an important role.
23. Beller and Zapf have shown that non-orthometalated complexes of triarylphosphites can couple activated aryl chlorides: A. Zapf, M. Beller. Chem. Eur J. 2000, 6, 1830-1833.
24. 11 pathway. This assumption is made on the basis of studies into the activation of palladacyclic precatalysts in Suzuki coupling reactions. See reference [2c] for leading references.