Tetraphosphine/palladium-catalyzed Heck reactions of aryl halides with disubstituted alkenes

Tetrahedron Letters

Volumn 44, Issue 46, 2003, Pages 8487-8491

  Kondolff, Isabelle ^a   Doucet, Henri ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Disubstituted alkene; Heck reaction; Palladium; Tetraphosphine

Indexed keywords

1,2,3,4 TETRAKIS(DIPHENYLPHOSPHINOMETHYL)CYCLOPENTANE; ALKENE DERIVATIVE; ALPHA METHYLSTYRENE; CROTONIC ACID METHYL ESTER; CYCLOPENTANE DERIVATIVE; HALIDE; METHACRYLIC ACID METHYL ESTER; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; STYRENE DERIVATIVE; TETRAPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; HECK REACTION; ISOMER; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0141956490     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.092     Document Type: Article

References (42)

1. For reviews on the palladium-catalyzed Heck reaction, see: (a) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates; Pergamon: Oxford, 1991; Vol. 4; (b) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. 1994, 33, 2379; (c) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions; Academic Press: London, 1997; (d) Reetz, M. T. Transition Metal Catalyzed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (e) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (f) Withcombe, N.; Hii (Mimi) K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (g) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
2. For reviews on the palladium-catalyzed Heck reaction, see: (a) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates; Pergamon: Oxford, 1991; Vol. 4; (b) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. 1994, 33, 2379; (c) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions; Academic Press: London, 1997; (d) Reetz, M. T. Transition Metal Catalyzed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (e) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (f) Withcombe, N.; Hii (Mimi) K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (g) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
3. For reviews on the palladium-catalyzed Heck reaction, see: (a) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates; Pergamon: Oxford, 1991; Vol. 4; (b) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. 1994, 33, 2379; (c) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions; Academic Press: London, 1997; (d) Reetz, M. T. Transition Metal Catalyzed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (e) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (f) Withcombe, N.; Hii (Mimi) K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (g) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
4. For reviews on the palladium-catalyzed Heck reaction, see: (a) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates; Pergamon: Oxford, 1991; Vol. 4; (b) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. 1994, 33, 2379; (c) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions; Academic Press: London, 1997; (d) Reetz, M. T. Transition Metal Catalyzed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (e) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (f) Withcombe, N.; Hii (Mimi) K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (g) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
5. For reviews on the palladium-catalyzed Heck reaction, see: (a) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates; Pergamon: Oxford, 1991; Vol. 4; (b) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. 1994, 33, 2379; (c) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions; Academic Press: London, 1997; (d) Reetz, M. T. Transition Metal Catalyzed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (e) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (f) Withcombe, N.; Hii (Mimi) K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (g) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
6. For reviews on the palladium-catalyzed Heck reaction, see: (a) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates; Pergamon: Oxford, 1991; Vol. 4; (b) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. 1994, 33, 2379; (c) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions; Academic Press: London, 1997; (d) Reetz, M. T. Transition Metal Catalyzed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (e) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (f) Withcombe, N.; Hii (Mimi) K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (g) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
7. For reviews on the palladium-catalyzed Heck reaction, see: (a) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds. Vinyl Substitution with Organopalladium Intermediates; Pergamon: Oxford, 1991; Vol. 4; (b) de Meijere, A.; Meyer, F. Angew. Chem., Int. Ed. 1994, 33, 2379; (c) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalyzed Organic Reactions; Academic Press: London, 1997; (d) Reetz, M. T. Transition Metal Catalyzed Reactions; Davies, S. G.; Murahashi, S.-I., Eds.; Blackwell Science: Oxford, 1999; (e) Beletskaya, I.; Cheprakov, A. Chem. Rev. 2000, 100, 3009; (f) Withcombe, N.; Hii (Mimi) K. K.; Gibson, S. Tetrahedron 2001, 57, 7449; (g) Littke, A.; Fu, G. Angew. Chem., Int. Ed. 2002, 41, 4176.
8. For examples of Heck reactions with alkyl cinnamates or crotonates, see: (a) Melpolder, J.; Heck, R. J. Org. Chem. 1976, 41, 265; (b) Cortese N.; Ziegler, C.; Hrnjez, B., Heck, R. J. Org. Chem. 1978, 43, 2952; (c) Busacca, C. ; Johnson, R. Tetrahedron Lett. 1992, 33, 165; (d) Moreno-Mañas, M.; Pérez, M.; Roser, P. Tetrahedron Lett. 1996, 37, 7449; (e) Gürtler, C.; Buchwald, S. Chem. Eur. J. 1999, 5, 3107; (f) Ohff, M.; Ohff, A.; Milstein D. Chem. Commun. 1999, 357; (g) Blettner, C.; König, W.; Stenzel, W.; Schotten, T. Tetrahedron Lett. 1999, 40, 2101; (h) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989; (i) Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; di Cosmo, A. Tetrahedron 2001, 57, 6071.
9. For examples of Heck reactions with alkyl cinnamates or crotonates, see: (a) Melpolder, J.; Heck, R. J. Org. Chem. 1976, 41, 265; (b) Cortese N.; Ziegler, C.; Hrnjez, B., Heck, R. J. Org. Chem. 1978, 43, 2952; (c) Busacca, C. ; Johnson, R. Tetrahedron Lett. 1992, 33, 165; (d) Moreno-Mañas, M.; Pérez, M.; Roser, P. Tetrahedron Lett. 1996, 37, 7449; (e) Gürtler, C.; Buchwald, S. Chem. Eur. J. 1999, 5, 3107; (f) Ohff, M.; Ohff, A.; Milstein D. Chem. Commun. 1999, 357; (g) Blettner, C.; König, W.; Stenzel, W.; Schotten, T. Tetrahedron Lett. 1999, 40, 2101; (h) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989; (i) Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; di Cosmo, A. Tetrahedron 2001, 57, 6071.
10. For examples of Heck reactions with alkyl cinnamates or crotonates, see: (a) Melpolder, J.; Heck, R. J. Org. Chem. 1976, 41, 265; (b) Cortese N.; Ziegler, C.; Hrnjez, B., Heck, R. J. Org. Chem. 1978, 43, 2952; (c) Busacca, C. ; Johnson, R. Tetrahedron Lett. 1992, 33, 165; (d) Moreno-Mañas, M.; Pérez, M.; Roser, P. Tetrahedron Lett. 1996, 37, 7449; (e) Gürtler, C.; Buchwald, S. Chem. Eur. J. 1999, 5, 3107; (f) Ohff, M.; Ohff, A.; Milstein D. Chem. Commun. 1999, 357; (g) Blettner, C.; König, W.; Stenzel, W.; Schotten, T. Tetrahedron Lett. 1999, 40, 2101; (h) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989; (i) Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; di Cosmo, A. Tetrahedron 2001, 57, 6071.
11. For examples of Heck reactions with alkyl cinnamates or crotonates, see: (a) Melpolder, J.; Heck, R. J. Org. Chem. 1976, 41, 265; (b) Cortese N.; Ziegler, C.; Hrnjez, B., Heck, R. J. Org. Chem. 1978, 43, 2952; (c) Busacca, C. ; Johnson, R. Tetrahedron Lett. 1992, 33, 165; (d) Moreno-Mañas, M.; Pérez, M.; Roser, P. Tetrahedron Lett. 1996, 37, 7449; (e) Gürtler, C.; Buchwald, S. Chem. Eur. J. 1999, 5, 3107; (f) Ohff, M.; Ohff, A.; Milstein D. Chem. Commun. 1999, 357; (g) Blettner, C.; König, W.; Stenzel, W.; Schotten, T. Tetrahedron Lett. 1999, 40, 2101; (h) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989; (i) Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; di Cosmo, A. Tetrahedron 2001, 57, 6071.
12. For examples of Heck reactions with alkyl cinnamates or crotonates, see: (a) Melpolder, J.; Heck, R. J. Org. Chem. 1976, 41, 265; (b) Cortese N.; Ziegler, C.; Hrnjez, B., Heck, R. J. Org. Chem. 1978, 43, 2952; (c) Busacca, C. ; Johnson, R. Tetrahedron Lett. 1992, 33, 165; (d) Moreno-Mañas, M.; Pérez, M.; Roser, P. Tetrahedron Lett. 1996, 37, 7449; (e) Gürtler, C.; Buchwald, S. Chem. Eur. J. 1999, 5, 3107; (f) Ohff, M.; Ohff, A.; Milstein D. Chem. Commun. 1999, 357; (g) Blettner, C.; König, W.; Stenzel, W.; Schotten, T. Tetrahedron Lett. 1999, 40, 2101; (h) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989; (i) Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; di Cosmo, A. Tetrahedron 2001, 57, 6071.
13. For examples of Heck reactions with alkyl cinnamates or crotonates, see: (a) Melpolder, J.; Heck, R. J. Org. Chem. 1976, 41, 265; (b) Cortese N.; Ziegler, C.; Hrnjez, B., Heck, R. J. Org. Chem. 1978, 43, 2952; (c) Busacca, C. ; Johnson, R. Tetrahedron Lett. 1992, 33, 165; (d) Moreno-Mañas, M.; Pérez, M.; Roser, P. Tetrahedron Lett. 1996, 37, 7449; (e) Gürtler, C.; Buchwald, S. Chem. Eur. J. 1999, 5, 3107; (f) Ohff, M.; Ohff, A.; Milstein D. Chem. Commun. 1999, 357; (g) Blettner, C.; König, W.; Stenzel, W.; Schotten, T. Tetrahedron Lett. 1999, 40, 2101; (h) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989; (i) Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; di Cosmo, A. Tetrahedron 2001, 57, 6071.
14. For examples of Heck reactions with alkyl cinnamates or crotonates, see: (a) Melpolder, J.; Heck, R. J. Org. Chem. 1976, 41, 265; (b) Cortese N.; Ziegler, C.; Hrnjez, B., Heck, R. J. Org. Chem. 1978, 43, 2952; (c) Busacca, C. ; Johnson, R. Tetrahedron Lett. 1992, 33, 165; (d) Moreno-Mañas, M.; Pérez, M.; Roser, P. Tetrahedron Lett. 1996, 37, 7449; (e) Gürtler, C.; Buchwald, S. Chem. Eur. J. 1999, 5, 3107; (f) Ohff, M.; Ohff, A.; Milstein D. Chem. Commun. 1999, 357; (g) Blettner, C.; König, W.; Stenzel, W.; Schotten, T. Tetrahedron Lett. 1999, 40, 2101; (h) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989; (i) Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; di Cosmo, A. Tetrahedron 2001, 57, 6071.
15. For examples of Heck reactions with alkyl cinnamates or crotonates, see: (a) Melpolder, J.; Heck, R. J. Org. Chem. 1976, 41, 265; (b) Cortese N.; Ziegler, C.; Hrnjez, B., Heck, R. J. Org. Chem. 1978, 43, 2952; (c) Busacca, C. ; Johnson, R. Tetrahedron Lett. 1992, 33, 165; (d) Moreno-Mañas, M.; Pérez, M.; Roser, P. Tetrahedron Lett. 1996, 37, 7449; (e) Gürtler, C.; Buchwald, S. Chem. Eur. J. 1999, 5, 3107; (f) Ohff, M.; Ohff, A.; Milstein D. Chem. Commun. 1999, 357; (g) Blettner, C.; König, W.; Stenzel, W.; Schotten, T. Tetrahedron Lett. 1999, 40, 2101; (h) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989; (i) Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; di Cosmo, A. Tetrahedron 2001, 57, 6071.
16. For examples of Heck reactions with alkyl cinnamates or crotonates, see: (a) Melpolder, J.; Heck, R. J. Org. Chem. 1976, 41, 265; (b) Cortese N.; Ziegler, C.; Hrnjez, B., Heck, R. J. Org. Chem. 1978, 43, 2952; (c) Busacca, C. ; Johnson, R. Tetrahedron Lett. 1992, 33, 165; (d) Moreno-Mañas, M.; Pérez, M.; Roser, P. Tetrahedron Lett. 1996, 37, 7449; (e) Gürtler, C.; Buchwald, S. Chem. Eur. J. 1999, 5, 3107; (f) Ohff, M.; Ohff, A.; Milstein D. Chem. Commun. 1999, 357; (g) Blettner, C.; König, W.; Stenzel, W.; Schotten, T. Tetrahedron Lett. 1999, 40, 2101; (h) Littke, A.; Fu, G. J. Am. Chem. Soc. 2001, 123, 6989; (i) Calo, V.; Nacci, A.; Monopoli, A.; Lopez, L.; di Cosmo, A. Tetrahedron 2001, 57, 6071.
17. For examples of Heck reactions with E-benzalacetone or E-benzalacetophenone, see: (a) Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236; (b) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fereli, W.; Ortar, G. Tetrahedron 1989, 45, 813.
18. For examples of Heck reactions with E-benzalacetone or E-benzalacetophenone, see: (a) Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236; (b) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fereli, W.; Ortar, G. Tetrahedron 1989, 45, 813.
19. For examples of Heck reactions with methyl methacrylate or α-methylstyrene, see: (a) Beller, M.; Riermeier, T. Tetrahedron Lett. 1996, 37, 6535; (b) Beller, M.; Riermeier T. Eur. J. Inorg. Chem. 1998, 1, 29; (c) Böhm, V.; Herrmann, W. Chem. Eur. J. 2000, 6, 1017; (d) Netherton, M.; Fu, G. Org. Lett. 2001, 3, 4295; (e) Albeniz, A.; Espinet, P.; Martin-Ruiz, B.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 11504; (f) Chandrasekhar, V.; Athimoolam, A. Org. Lett. 2002, 4, 2113 and Refs. 2e, 2h.
20. For examples of Heck reactions with methyl methacrylate or α-methylstyrene, see: (a) Beller, M.; Riermeier, T. Tetrahedron Lett. 1996, 37, 6535; (b) Beller, M.; Riermeier T. Eur. J. Inorg. Chem. 1998, 1, 29; (c) Böhm, V.; Herrmann, W. Chem. Eur. J. 2000, 6, 1017; (d) Netherton, M.; Fu, G. Org. Lett. 2001, 3, 4295; (e) Albeniz, A.; Espinet, P.; Martin-Ruiz, B.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 11504; (f) Chandrasekhar, V.; Athimoolam, A. Org. Lett. 2002, 4, 2113 and Refs. 2e, 2h.
21. For examples of Heck reactions with methyl methacrylate or α-methylstyrene, see: (a) Beller, M.; Riermeier, T. Tetrahedron Lett. 1996, 37, 6535; (b) Beller, M.; Riermeier T. Eur. J. Inorg. Chem. 1998, 1, 29; (c) Böhm, V.; Herrmann, W. Chem. Eur. J. 2000, 6, 1017; (d) Netherton, M.; Fu, G. Org. Lett. 2001, 3, 4295; (e) Albeniz, A.; Espinet, P.; Martin-Ruiz, B.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 11504; (f) Chandrasekhar, V.; Athimoolam, A. Org. Lett. 2002, 4, 2113 and Refs. 2e, 2h.
22. For examples of Heck reactions with methyl methacrylate or α-methylstyrene, see: (a) Beller, M.; Riermeier, T. Tetrahedron Lett. 1996, 37, 6535; (b) Beller, M.; Riermeier T. Eur. J. Inorg. Chem. 1998, 1, 29; (c) Böhm, V.; Herrmann, W. Chem. Eur. J. 2000, 6, 1017; (d) Netherton, M.; Fu, G. Org. Lett. 2001, 3, 4295; (e) Albeniz, A.; Espinet, P.; Martin-Ruiz, B.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 11504; (f) Chandrasekhar, V.; Athimoolam, A. Org. Lett. 2002, 4, 2113 and Refs. 2e, 2h.
23. For examples of Heck reactions with methyl methacrylate or α-methylstyrene, see: (a) Beller, M.; Riermeier, T. Tetrahedron Lett. 1996, 37, 6535; (b) Beller, M.; Riermeier T. Eur. J. Inorg. Chem. 1998, 1, 29; (c) Böhm, V.; Herrmann, W. Chem. Eur. J. 2000, 6, 1017; (d) Netherton, M.; Fu, G. Org. Lett. 2001, 3, 4295; (e) Albeniz, A.; Espinet, P.; Martin-Ruiz, B.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 11504; (f) Chandrasekhar, V.; Athimoolam, A. Org. Lett. 2002, 4, 2113 and Refs. 2e, 2h.
24. For examples of Heck reactions with methyl methacrylate or α-methylstyrene, see: (a) Beller, M.; Riermeier, T. Tetrahedron Lett. 1996, 37, 6535; (b) Beller, M.; Riermeier T. Eur. J. Inorg. Chem. 1998, 1, 29; (c) Böhm, V.; Herrmann, W. Chem. Eur. J. 2000, 6, 1017; (d) Netherton, M.; Fu, G. Org. Lett. 2001, 3, 4295; (e) Albeniz, A.; Espinet, P.; Martin-Ruiz, B.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 11504; (f) Chandrasekhar, V.; Athimoolam, A. Org. Lett. 2002, 4, 2113 and Refs. 2e, 2h.
25. For recent examples of Heck reactions catalyzed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T. ; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. 1995, 34, 1844; (b) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (c) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (d) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (e) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (f) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (g) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (h) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779.
26. For recent examples of Heck reactions catalyzed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T. ; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. 1995, 34, 1844; (b) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (c) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (d) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (e) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (f) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (g) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (h) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779.
27. For recent examples of Heck reactions catalyzed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T. ; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. 1995, 34, 1844; (b) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (c) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (d) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (e) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (f) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (g) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (h) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779.
28. For recent examples of Heck reactions catalyzed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T. ; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. 1995, 34, 1844; (b) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (c) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (d) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (e) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (f) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (g) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (h) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779.
29. For recent examples of Heck reactions catalyzed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T. ; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. 1995, 34, 1844; (b) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (c) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (d) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (e) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (f) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (g) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (h) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779.
30. For recent examples of Heck reactions catalyzed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T. ; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. 1995, 34, 1844; (b) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (c) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (d) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (e) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (f) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (g) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (h) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779.
31. For recent examples of Heck reactions catalyzed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T. ; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. 1995, 34, 1844; (b) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (c) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (d) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (e) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (f) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (g) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (h) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779.
32. For recent examples of Heck reactions catalyzed by palladacycles, see: (a) Herrmann, W. A.; Brossmer, C.; Öfele, K.; Reisinger, C.; Riermeier, T. ; Beller, M.; Fisher, H. Angew. Chem., Int. Ed. 1995, 34, 1844; (b) Ohff, M.; Ohff, A.; Boom, M.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687; (c) Albisson, D.; Bedford, R.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793; (d) Ohff, M.; Ohff, A.; Milstein, D. Chem. Commun. 1999, 357; (e) Miyazaki, F.; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379; (f) Bergbreiter, D.; Osburn, P.; Liu, Y.-S. J. Am. Chem. Soc. 1999, 121, 9531; (g) Gai, X.; Grigg, R.; Ramzan, I.; Sridharan, V.; Collard, S.; Muir, J. Chem. Commun. 2000, 2053; (h) Gibson, S.; Foster, D.; Eastham, D.; Tooze, R.; Cole-Hamilton, D. Chem. Commun. 2001, 779.
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42. 3) δ: 7.44 (dd, 2H, J=5.3 and 8.3 Hz), 7.04 (t, 2H, J=8.3 Hz), 6.08 (s, 1H), 3.74 (s, 3H), 2.53 (s, 3H).