Heck reaction of aryl halides with linear or cyclic alkenes catalysed by a tetraphosphine/palladium catalyst

Tetrahedron Letters

Volumn 44, Issue 6, 2003, Pages 1221-1225

  Berthiol, Florian ^a   Doucet, Henri ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMOTHIOPHENE; 2 BROMOTOLUENE; 2,6 DIMETHYLBROMOBENZENE; 3 BROMOPYRIDINE; 3 BROMOQUINOLINE; 3,5 BISTRIFLUOROMETHYLBROMOBENZENE; 4 BROMOACETOPHENONE; 4 BROMOANISOLE; 4 BROMOBENZALDEHYDE; 4 BROMOBENZONITRILE; 4 BROMOBENZOPHENONE; 4 TRIFLUOROMETHYLBROMOBENZENE; 9 BROMOANTHRACENE; ALKENE; ALKENE DERIVATIVE; BROMOBENZENE; HALIDE; IODOBENZENE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; HECK REACTION; ISOMER;

HUMAN ECHOVIRUS 1;

EID: 0037415535     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02788-0     Document Type: Article

References (38)

1. For reviews on the palladium-catalysed Heck reaction, see: (a) Heck, R. F. Palladium Reagents in Organic Syntheses, Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Academic Press: London, 1985, p. 2.; (b) Heck, R. F. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates. Pergamon: Oxford, 1991; Vol. 4; (c) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (d) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalysed Organic Reactions; Academic Press: London, 1997; (e) Reetz, M. T. Transition Metal Catalysed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (f) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (g) Withcombe, N.; Hii (Mimi), K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (h) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
2. For reviews on the palladium-catalysed Heck reaction, see: (a) Heck, R. F. Palladium Reagents in Organic Syntheses, Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Academic Press: London, 1985, p. 2.; (b) Heck, R. F. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates. Pergamon: Oxford, 1991; Vol. 4; (c) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (d) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalysed Organic Reactions; Academic Press: London, 1997; (e) Reetz, M. T. Transition Metal Catalysed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (f) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (g) Withcombe, N.; Hii (Mimi), K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (h) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
3. For reviews on the palladium-catalysed Heck reaction, see: (a) Heck, R. F. Palladium Reagents in Organic Syntheses, Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Academic Press: London, 1985, p. 2.; (b) Heck, R. F. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates. Pergamon: Oxford, 1991; Vol. 4; (c) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (d) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalysed Organic Reactions; Academic Press: London, 1997; (e) Reetz, M. T. Transition Metal Catalysed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (f) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (g) Withcombe, N.; Hii (Mimi), K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (h) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
4. For reviews on the palladium-catalysed Heck reaction, see: (a) Heck, R. F. Palladium Reagents in Organic Syntheses, Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Academic Press: London, 1985, p. 2.; (b) Heck, R. F. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates. Pergamon: Oxford, 1991; Vol. 4; (c) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (d) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalysed Organic Reactions; Academic Press: London, 1997; (e) Reetz, M. T. Transition Metal Catalysed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (f) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (g) Withcombe, N.; Hii (Mimi), K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (h) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
5. For reviews on the palladium-catalysed Heck reaction, see: (a) Heck, R. F. Palladium Reagents in Organic Syntheses, Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Academic Press: London, 1985, p. 2.; (b) Heck, R. F. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates. Pergamon: Oxford, 1991; Vol. 4; (c) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (d) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalysed Organic Reactions; Academic Press: London, 1997; (e) Reetz, M. T. Transition Metal Catalysed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (f) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (g) Withcombe, N.; Hii (Mimi), K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (h) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
6. For reviews on the palladium-catalysed Heck reaction, see: (a) Heck, R. F. Palladium Reagents in Organic Syntheses, Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Academic Press: London, 1985, p. 2.; (b) Heck, R. F. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates. Pergamon: Oxford, 1991; Vol. 4; (c) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (d) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalysed Organic Reactions; Academic Press: London, 1997; (e) Reetz, M. T. Transition Metal Catalysed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (f) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (g) Withcombe, N.; Hii (Mimi), K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (h) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
7. For reviews on the palladium-catalysed Heck reaction, see: (a) Heck, R. F. Palladium Reagents in Organic Syntheses, Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Academic Press: London, 1985, p. 2.; (b) Heck, R. F. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates. Pergamon: Oxford, 1991; Vol. 4; (c) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (d) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalysed Organic Reactions; Academic Press: London, 1997; (e) Reetz, M. T. Transition Metal Catalysed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (f) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (g) Withcombe, N.; Hii (Mimi), K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (h) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
8. For reviews on the palladium-catalysed Heck reaction, see: (a) Heck, R. F. Palladium Reagents in Organic Syntheses, Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Academic Press: London, 1985, p. 2.; (b) Heck, R. F. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates. Pergamon: Oxford, 1991; Vol. 4; (c) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379; (d) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalysed Organic Reactions; Academic Press: London, 1997; (e) Reetz, M. T. Transition Metal Catalysed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (f) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (g) Withcombe, N.; Hii (Mimi), K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (h) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
9. For examples of Heck reaction using aryl halides and linear alkenes, see: (a) Larock, R.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629; (b) Mabic, S.; Lepoittevin, J.-P. Tetrahedron Lett. 1995, 36, 1705; (c) Bräse, S.; Rümper, J.; Voigt, K.; Albecq, S.; Thurau, G.; Villard, R.; Waegell, B.; de Meijere, A. Eur. J. Org. Chem. 1998, 671; (d) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989.
10. For examples of Heck reaction using aryl halides and linear alkenes, see: (a) Larock, R.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629; (b) Mabic, S.; Lepoittevin, J.-P. Tetrahedron Lett. 1995, 36, 1705; (c) Bräse, S.; Rümper, J.; Voigt, K.; Albecq, S.; Thurau, G.; Villard, R.; Waegell, B.; de Meijere, A. Eur. J. Org. Chem. 1998, 671; (d) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989.
11. For examples of Heck reaction using aryl halides and linear alkenes, see: (a) Larock, R.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629; (b) Mabic, S.; Lepoittevin, J.-P. Tetrahedron Lett. 1995, 36, 1705; (c) Bräse, S.; Rümper, J.; Voigt, K.; Albecq, S.; Thurau, G.; Villard, R.; Waegell, B.; de Meijere, A. Eur. J. Org. Chem. 1998, 671; (d) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989.
12. For examples of Heck reaction using aryl halides and linear alkenes, see: (a) Larock, R.; Leung, W.-Y.; Stolz-Dunn, S. Tetrahedron Lett. 1989, 30, 6629; (b) Mabic, S.; Lepoittevin, J.-P. Tetrahedron Lett. 1995, 36, 1705; (c) Bräse, S.; Rümper, J.; Voigt, K.; Albecq, S.; Thurau, G.; Villard, R.; Waegell, B.; de Meijere, A. Eur. J. Org. Chem. 1998, 671; (d) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989.
13. For examples of Heck reaction using aryl halides and cyclic alkenes, see: (a) Larock, R.; Baker, B. Tetrahedron Lett. 1988, 29, 905; (b) Larock, R.; Gong, W.; Baker, B. Tetrahedron Lett. 1989, 30, 2603; (c) Larock, R.; Gong, W. J. Org. Chem. 1989, 54, 2047; (d) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087; (e) Gron, L.; Tinsley, A. Tetrahedron Lett. 1999, 40, 227; (f) Hartung, C.; Köhler, K.; Beller, M. Org. Lett. 1999, 1, 709; (g) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990; (h) Buechner, I.; Metz, P. Tetrahedron Lett. 2001, 42, 5381.
14. For examples of Heck reaction using aryl halides and cyclic alkenes, see: (a) Larock, R.; Baker, B. Tetrahedron Lett. 1988, 29, 905; (b) Larock, R.; Gong, W.; Baker, B. Tetrahedron Lett. 1989, 30, 2603; (c) Larock, R.; Gong, W. J. Org. Chem. 1989, 54, 2047; (d) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087; (e) Gron, L.; Tinsley, A. Tetrahedron Lett. 1999, 40, 227; (f) Hartung, C.; Köhler, K.; Beller, M. Org. Lett. 1999, 1, 709; (g) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990; (h) Buechner, I.; Metz, P. Tetrahedron Lett. 2001, 42, 5381.
15. For examples of Heck reaction using aryl halides and cyclic alkenes, see: (a) Larock, R.; Baker, B. Tetrahedron Lett. 1988, 29, 905; (b) Larock, R.; Gong, W.; Baker, B. Tetrahedron Lett. 1989, 30, 2603; (c) Larock, R.; Gong, W. J. Org. Chem. 1989, 54, 2047; (d) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087; (e) Gron, L.; Tinsley, A. Tetrahedron Lett. 1999, 40, 227; (f) Hartung, C.; Köhler, K.; Beller, M. Org. Lett. 1999, 1, 709; (g) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990; (h) Buechner, I.; Metz, P. Tetrahedron Lett. 2001, 42, 5381.
16. For examples of Heck reaction using aryl halides and cyclic alkenes, see: (a) Larock, R.; Baker, B. Tetrahedron Lett. 1988, 29, 905; (b) Larock, R.; Gong, W.; Baker, B. Tetrahedron Lett. 1989, 30, 2603; (c) Larock, R.; Gong, W. J. Org. Chem. 1989, 54, 2047; (d) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087; (e) Gron, L.; Tinsley, A. Tetrahedron Lett. 1999, 40, 227; (f) Hartung, C.; Köhler, K.; Beller, M. Org. Lett. 1999, 1, 709; (g) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990; (h) Buechner, I.; Metz, P. Tetrahedron Lett. 2001, 42, 5381.
17. For examples of Heck reaction using aryl halides and cyclic alkenes, see: (a) Larock, R.; Baker, B. Tetrahedron Lett. 1988, 29, 905; (b) Larock, R.; Gong, W.; Baker, B. Tetrahedron Lett. 1989, 30, 2603; (c) Larock, R.; Gong, W. J. Org. Chem. 1989, 54, 2047; (d) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087; (e) Gron, L.; Tinsley, A. Tetrahedron Lett. 1999, 40, 227; (f) Hartung, C.; Köhler, K.; Beller, M. Org. Lett. 1999, 1, 709; (g) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990; (h) Buechner, I.; Metz, P. Tetrahedron Lett. 2001, 42, 5381.
18. For examples of Heck reaction using aryl halides and cyclic alkenes, see: (a) Larock, R.; Baker, B. Tetrahedron Lett. 1988, 29, 905; (b) Larock, R.; Gong, W.; Baker, B. Tetrahedron Lett. 1989, 30, 2603; (c) Larock, R.; Gong, W. J. Org. Chem. 1989, 54, 2047; (d) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087; (e) Gron, L.; Tinsley, A. Tetrahedron Lett. 1999, 40, 227; (f) Hartung, C.; Köhler, K.; Beller, M. Org. Lett. 1999, 1, 709; (g) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990; (h) Buechner, I.; Metz, P. Tetrahedron Lett. 2001, 42, 5381.
19. For examples of Heck reaction using aryl halides and cyclic alkenes, see: (a) Larock, R.; Baker, B. Tetrahedron Lett. 1988, 29, 905; (b) Larock, R.; Gong, W.; Baker, B. Tetrahedron Lett. 1989, 30, 2603; (c) Larock, R.; Gong, W. J. Org. Chem. 1989, 54, 2047; (d) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087; (e) Gron, L.; Tinsley, A. Tetrahedron Lett. 1999, 40, 227; (f) Hartung, C.; Köhler, K.; Beller, M. Org. Lett. 1999, 1, 709; (g) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990; (h) Buechner, I.; Metz, P. Tetrahedron Lett. 2001, 42, 5381.
20. For examples of Heck reaction using aryl halides and cyclic alkenes, see: (a) Larock, R.; Baker, B. Tetrahedron Lett. 1988, 29, 905; (b) Larock, R.; Gong, W.; Baker, B. Tetrahedron Lett. 1989, 30, 2603; (c) Larock, R.; Gong, W. J. Org. Chem. 1989, 54, 2047; (d) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087; (e) Gron, L.; Tinsley, A. Tetrahedron Lett. 1999, 40, 227; (f) Hartung, C.; Köhler, K.; Beller, M. Org. Lett. 1999, 1, 709; (g) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990; (h) Buechner, I.; Metz, P. Tetrahedron Lett. 2001, 42, 5381.
21. For recent examples of Heck reactions catalysed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.; Riermeier, T.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357; (c) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (d) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (e) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (f) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (g) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (h) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (i) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779; (j) Iyer, S.; Jayanthi, A. Tetrahedron Lett. 2001, 42, 7877.
22. For recent examples of Heck reactions catalysed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.; Riermeier, T.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357; (c) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (d) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (e) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (f) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (g) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (h) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (i) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779; (j) Iyer, S.; Jayanthi, A. Tetrahedron Lett. 2001, 42, 7877.
23. For recent examples of Heck reactions catalysed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.; Riermeier, T.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357; (c) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (d) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (e) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (f) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (g) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (h) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (i) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779; (j) Iyer, S.; Jayanthi, A. Tetrahedron Lett. 2001, 42, 7877.
24. For recent examples of Heck reactions catalysed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.; Riermeier, T.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357; (c) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (d) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (e) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (f) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (g) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (h) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (i) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779; (j) Iyer, S.; Jayanthi, A. Tetrahedron Lett. 2001, 42, 7877.
25. For recent examples of Heck reactions catalysed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.; Riermeier, T.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357; (c) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (d) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (e) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (f) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (g) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (h) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (i) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779; (j) Iyer, S.; Jayanthi, A. Tetrahedron Lett. 2001, 42, 7877.
26. For recent examples of Heck reactions catalysed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.; Riermeier, T.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357; (c) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (d) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (e) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (f) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (g) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (h) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (i) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779; (j) Iyer, S.; Jayanthi, A. Tetrahedron Lett. 2001, 42, 7877.
27. For recent examples of Heck reactions catalysed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.; Riermeier, T.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357; (c) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (d) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (e) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (f) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (g) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (h) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (i) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779; (j) Iyer, S.; Jayanthi, A. Tetrahedron Lett. 2001, 42, 7877.
28. For recent examples of Heck reactions catalysed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.; Riermeier, T.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357; (c) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (d) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (e) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (f) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (g) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (h) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (i) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779; (j) Iyer, S.; Jayanthi, A. Tetrahedron Lett. 2001, 42, 7877.
29. For recent examples of Heck reactions catalysed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.; Riermeier, T.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357; (c) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (d) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (e) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (f) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (g) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (h) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (i) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779; (j) Iyer, S.; Jayanthi, A. Tetrahedron Lett. 2001, 42, 7877.
30. For recent examples of Heck reactions catalysed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T.; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844; (b) Herrmann, W. A.; Brossmer, C.; Reisinger, C.; Riermeier, T.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357; (c) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (d) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (e) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (f) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (g) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (h) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (i) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779; (j) Iyer, S.; Jayanthi, A. Tetrahedron Lett. 2001, 42, 7877.
31. For a review on the synthesis of polypodal diphenylphosphine ligands, see: Laurenti D., Santelli M. Org. Prep. Proc. Int. 31:1999;245-294.
32. Laurenti D., Feuerstein M., Pèpe G., Doucet H., Santelli M. J. Org. Chem. 66:2001;1633.
33. Feuerstein M., Laurenti D., Bougeant C., Doucet H., Santelli M. Chem. Commun. 2001;325.
34. Feuerstein M., Doucet H., Santelli M. J. Org. Chem. 66:2001;5923.
35. Feuerstein M., Doucet H., Santelli M. Synlett. 2001;1980.
36. Feuerstein M., Doucet H., Santelli M. Tetrahedron Lett. 43:2002;2191.
37. Berthiol F., Feuerstein M., Doucet H., Santelli M. Tetrahedron Lett. 43:2002;2191.
38. +].