Macromolecular effect: Synthesis of a ferrocenylmethylphosphine-containing polymer as highly efficient ligands for room-temperature palladium(0)-catalyzed Suzuki cross-coupling reactions of aryl chlorides

Journal of the American Chemical Society

Volumn 125, Issue 10, 2003, Pages 2856-2857

  Hu, Qiao Sheng ^a   Lu, Yong ^a   Tang, Zhen Yu ^a   Yu, Hong Bin ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; CHLORIDE; FERROCENE DERIVATIVE; LIGAND; METAL COMPLEX; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYMER;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TEMPERATURE;

EID: 0037433563     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029021e     Document Type: Article

References (35)

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18. For monophosphine-containing polymers as ligands for Pd(0)-catalyzed reactions: (a) Colacot, T. J.; Gore, E. S.; Kuber, A. Organometallics 2002, 21, 3301. (b) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820. (c) Park, H.-J.; Han, J. W.; Seo, H.; Jang, H.-Y.; Chung, Y. K.; Suh, J. J. Mol. Catal. A: Chem. 2001, 174, 151. (d) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058. (e) Inada, K.; Miyaura, N. Tetrahedron 2000, 56, 8661. (f) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522. (g) Edwards, C. W.; Shipton, M. R.; Wills, M. Tetrahedron Lett. 2000, 41, 8615. (h) Fenger, I.; Drian, C. L. Tetrahedron Lett. 1998, 39, 4287. (i) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (j) Jang, S.-B. Tetrahedron Lett. 1997, 38, 1793. (k) Anderson, C.-M.; Karabelas, K.; Hallberg, A. J. Org. Chem. 1985, 50, 3891. (l) Trost, B. M.; Keinan, E. J. Am. Chem. Soc. 1978, 100, 7779.
19. For monophosphine-containing polymers as ligands for Pd(0)-catalyzed reactions: (a) Colacot, T. J.; Gore, E. S.; Kuber, A. Organometallics 2002, 21, 3301. (b) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820. (c) Park, H.-J.; Han, J. W.; Seo, H.; Jang, H.-Y.; Chung, Y. K.; Suh, J. J. Mol. Catal. A: Chem. 2001, 174, 151. (d) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058. (e) Inada, K.; Miyaura, N. Tetrahedron 2000, 56, 8661. (f) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522. (g) Edwards, C. W.; Shipton, M. R.; Wills, M. Tetrahedron Lett. 2000, 41, 8615. (h) Fenger, I.; Drian, C. L. Tetrahedron Lett. 1998, 39, 4287. (i) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (j) Jang, S.-B. Tetrahedron Lett. 1997, 38, 1793. (k) Anderson, C.-M.; Karabelas, K.; Hallberg, A. J. Org. Chem. 1985, 50, 3891. (l) Trost, B. M.; Keinan, E. J. Am. Chem. Soc. 1978, 100, 7779.
20. For monophosphine-containing polymers as ligands for Pd(0)-catalyzed reactions: (a) Colacot, T. J.; Gore, E. S.; Kuber, A. Organometallics 2002, 21, 3301. (b) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820. (c) Park, H.-J.; Han, J. W.; Seo, H.; Jang, H.-Y.; Chung, Y. K.; Suh, J. J. Mol. Catal. A: Chem. 2001, 174, 151. (d) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058. (e) Inada, K.; Miyaura, N. Tetrahedron 2000, 56, 8661. (f) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522. (g) Edwards, C. W.; Shipton, M. R.; Wills, M. Tetrahedron Lett. 2000, 41, 8615. (h) Fenger, I.; Drian, C. L. Tetrahedron Lett. 1998, 39, 4287. (i) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (j) Jang, S.-B. Tetrahedron Lett. 1997, 38, 1793. (k) Anderson, C.-M.; Karabelas, K.; Hallberg, A. J. Org. Chem. 1985, 50, 3891. (l) Trost, B. M.; Keinan, E. J. Am. Chem. Soc. 1978, 100, 7779.
21. For monophosphine-containing polymers as ligands for Pd(0)-catalyzed reactions: (a) Colacot, T. J.; Gore, E. S.; Kuber, A. Organometallics 2002, 21, 3301. (b) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820. (c) Park, H.-J.; Han, J. W.; Seo, H.; Jang, H.-Y.; Chung, Y. K.; Suh, J. J. Mol. Catal. A: Chem. 2001, 174, 151. (d) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058. (e) Inada, K.; Miyaura, N. Tetrahedron 2000, 56, 8661. (f) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522. (g) Edwards, C. W.; Shipton, M. R.; Wills, M. Tetrahedron Lett. 2000, 41, 8615. (h) Fenger, I.; Drian, C. L. Tetrahedron Lett. 1998, 39, 4287. (i) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (j) Jang, S.-B. Tetrahedron Lett. 1997, 38, 1793. (k) Anderson, C.-M.; Karabelas, K.; Hallberg, A. J. Org. Chem. 1985, 50, 3891. (l) Trost, B. M.; Keinan, E. J. Am. Chem. Soc. 1978, 100, 7779.
22. For monophosphine-containing polymers as ligands for Pd(0)-catalyzed reactions: (a) Colacot, T. J.; Gore, E. S.; Kuber, A. Organometallics 2002, 21, 3301. (b) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820. (c) Park, H.-J.; Han, J. W.; Seo, H.; Jang, H.-Y.; Chung, Y. K.; Suh, J. J. Mol. Catal. A: Chem. 2001, 174, 151. (d) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058. (e) Inada, K.; Miyaura, N. Tetrahedron 2000, 56, 8661. (f) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522. (g) Edwards, C. W.; Shipton, M. R.; Wills, M. Tetrahedron Lett. 2000, 41, 8615. (h) Fenger, I.; Drian, C. L. Tetrahedron Lett. 1998, 39, 4287. (i) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (j) Jang, S.-B. Tetrahedron Lett. 1997, 38, 1793. (k) Anderson, C.-M.; Karabelas, K.; Hallberg, A. J. Org. Chem. 1985, 50, 3891. (l) Trost, B. M.; Keinan, E. J. Am. Chem. Soc. 1978, 100, 7779.
23. For monophosphine-containing polymers as ligands for Pd(0)-catalyzed reactions: (a) Colacot, T. J.; Gore, E. S.; Kuber, A. Organometallics 2002, 21, 3301. (b) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820. (c) Park, H.-J.; Han, J. W.; Seo, H.; Jang, H.-Y.; Chung, Y. K.; Suh, J. J. Mol. Catal. A: Chem. 2001, 174, 151. (d) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058. (e) Inada, K.; Miyaura, N. Tetrahedron 2000, 56, 8661. (f) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522. (g) Edwards, C. W.; Shipton, M. R.; Wills, M. Tetrahedron Lett. 2000, 41, 8615. (h) Fenger, I.; Drian, C. L. Tetrahedron Lett. 1998, 39, 4287. (i) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (j) Jang, S.-B. Tetrahedron Lett. 1997, 38, 1793. (k) Anderson, C.-M.; Karabelas, K.; Hallberg, A. J. Org. Chem. 1985, 50, 3891. (l) Trost, B. M.; Keinan, E. J. Am. Chem. Soc. 1978, 100, 7779.
24. For monophosphine-containing polymers as ligands for Pd(0)-catalyzed reactions: (a) Colacot, T. J.; Gore, E. S.; Kuber, A. Organometallics 2002, 21, 3301. (b) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820. (c) Park, H.-J.; Han, J. W.; Seo, H.; Jang, H.-Y.; Chung, Y. K.; Suh, J. J. Mol. Catal. A: Chem. 2001, 174, 151. (d) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058. (e) Inada, K.; Miyaura, N. Tetrahedron 2000, 56, 8661. (f) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522. (g) Edwards, C. W.; Shipton, M. R.; Wills, M. Tetrahedron Lett. 2000, 41, 8615. (h) Fenger, I.; Drian, C. L. Tetrahedron Lett. 1998, 39, 4287. (i) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (j) Jang, S.-B. Tetrahedron Lett. 1997, 38, 1793. (k) Anderson, C.-M.; Karabelas, K.; Hallberg, A. J. Org. Chem. 1985, 50, 3891. (l) Trost, B. M.; Keinan, E. J. Am. Chem. Soc. 1978, 100, 7779.
25. For monophosphine-containing polymers as ligands for Pd(0)-catalyzed reactions: (a) Colacot, T. J.; Gore, E. S.; Kuber, A. Organometallics 2002, 21, 3301. (b) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820. (c) Park, H.-J.; Han, J. W.; Seo, H.; Jang, H.-Y.; Chung, Y. K.; Suh, J. J. Mol. Catal. A: Chem. 2001, 174, 151. (d) Bergbreiter, D. E.; Osburn, P. L.; Wilson, A.; Sink, E. M. J. Am. Chem. Soc. 2000, 122, 9058. (e) Inada, K.; Miyaura, N. Tetrahedron 2000, 56, 8661. (f) Gilbertson, S. R.; Collibee, S. E.; Agarkov, A. J. Am. Chem. Soc. 2000, 122, 6522. (g) Edwards, C. W.; Shipton, M. R.; Wills, M. Tetrahedron Lett. 2000, 41, 8615. (h) Fenger, I.; Drian, C. L. Tetrahedron Lett. 1998, 39, 4287. (i) Uozumi, Y.; Danjo, H.; Hayashi, T. Tetrahedron Lett. 1998, 39, 8303. (j) Jang, S.-B. Tetrahedron Lett. 1997, 38, 1793. (k) Anderson, C.-M.; Karabelas, K.; Hallberg, A. J. Org. Chem. 1985, 50, 3891. (l) Trost, B. M.; Keinan, E. J. Am. Chem. Soc. 1978, 100, 7779.
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