Divergent Behavior of Palladium(II) and Platinum(II) in the Metalation of 1,3-Di(2-pyridyl)henzene

Organometallics

Volumn 18, Issue 17, 1999, Pages 3337-3341

  Cárdenas, Diego J ^a   Echavarren, Antonio M ^a   Ramírez De Arellano, M Carmen ^b,c  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF MURCIA   (Spain)

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038550611     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990125g     Document Type: Article

References (61)

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10. For synthetic applications of the Herrmann palladacycle: (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359. (c) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem, 1996, 108, 51. (d) Tietze, L. F.; Nöbel, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259. (e) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535. (f) Prinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1289. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073. (h) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (i) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135. (j) Dyker, G.; Kellner, A. J. Organomet. Chem. 1998, 555, 141. (k) Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
11. For synthetic applications of the Herrmann palladacycle: (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359. (c) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem, 1996, 108, 51. (d) Tietze, L. F.; Nöbel, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259. (e) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535. (f) Prinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1289. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073. (h) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (i) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135. (j) Dyker, G.; Kellner, A. J. Organomet. Chem. 1998, 555, 141. (k) Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
12. For synthetic applications of the Herrmann palladacycle: (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359. (c) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem, 1996, 108, 51. (d) Tietze, L. F.; Nöbel, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259. (e) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535. (f) Prinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1289. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073. (h) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (i) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135. (j) Dyker, G.; Kellner, A. J. Organomet. Chem. 1998, 555, 141. (k) Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
13. For synthetic applications of the Herrmann palladacycle: (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359. (c) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem, 1996, 108, 51. (d) Tietze, L. F.; Nöbel, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259. (e) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535. (f) Prinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1289. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073. (h) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (i) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135. (j) Dyker, G.; Kellner, A. J. Organomet. Chem. 1998, 555, 141. (k) Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
14. For synthetic applications of the Herrmann palladacycle: (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359. (c) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem, 1996, 108, 51. (d) Tietze, L. F.; Nöbel, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259. (e) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535. (f) Prinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1289. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073. (h) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (i) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135. (j) Dyker, G.; Kellner, A. J. Organomet. Chem. 1998, 555, 141. (k) Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
15. For synthetic applications of the Herrmann palladacycle: (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359. (c) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem, 1996, 108, 51. (d) Tietze, L. F.; Nöbel, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259. (e) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535. (f) Prinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1289. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073. (h) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (i) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135. (j) Dyker, G.; Kellner, A. J. Organomet. Chem. 1998, 555, 141. (k) Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
16. For synthetic applications of the Herrmann palladacycle: (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359. (c) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem, 1996, 108, 51. (d) Tietze, L. F.; Nöbel, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259. (e) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535. (f) Prinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1289. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073. (h) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (i) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135. (j) Dyker, G.; Kellner, A. J. Organomet. Chem. 1998, 555, 141. (k) Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
17. For synthetic applications of the Herrmann palladacycle: (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359. (c) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem, 1996, 108, 51. (d) Tietze, L. F.; Nöbel, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259. (e) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535. (f) Prinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1289. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073. (h) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (i) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135. (j) Dyker, G.; Kellner, A. J. Organomet. Chem. 1998, 555, 141. (k) Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
18. For synthetic applications of the Herrmann palladacycle: (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359. (c) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem, 1996, 108, 51. (d) Tietze, L. F.; Nöbel, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259. (e) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535. (f) Prinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1289. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073. (h) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (i) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135. (j) Dyker, G.; Kellner, A. J. Organomet. Chem. 1998, 555, 141. (k) Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
19. For synthetic applications of the Herrmann palladacycle: (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359. (c) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem, 1996, 108, 51. (d) Tietze, L. F.; Nöbel, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259. (e) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535. (f) Prinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1289. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073. (h) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (i) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135. (j) Dyker, G.; Kellner, A. J. Organomet. Chem. 1998, 555, 141. (k) Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
20. For synthetic applications of the Herrmann palladacycle: (a) Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848. (b) Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359. (c) Herrmann, W. A.; Reisinger, C.-P.; Öfele, K.; Brossmer, C.; Beller, M.; Fischer, H. J. Mol. Catal. A: Chem, 1996, 108, 51. (d) Tietze, L. F.; Nöbel, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 2259. (e) Beller, M.; Riermeier, T. H. Tetrahedron Lett. 1996, 37, 6535. (f) Prinz, P.; Lansky, A.; Haumann, T.; Boese, R.; Noltemeyer, M.; Knieriem, B.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1289. (g) Beller, M.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073. (h) Hennings, D. D.; Iwasa, S.; Rawal, V. H. J. Org. Chem. 1997, 62, 2. (i) Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135. (j) Dyker, G.; Kellner, A. J. Organomet. Chem. 1998, 555, 141. (k) Beller, M.; Riermeier, T. H. Eur. J. Inorg. Chem. 1998, 29.
21. Orthopalladated triaryl phosphites as catalysts: (a) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (b) Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793. Peripalladated tri(1-naphthyl)phosphine catalysts: (c) Spescha, M.; Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361.
22. Orthopalladated triaryl phosphites as catalysts: (a) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (b) Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793. Peripalladated tri(1-naphthyl)phosphine catalysts: (c) Spescha, M.; Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361.
23. Orthopalladated triaryl phosphites as catalysts: (a) Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095. (b) Albisson, D. A.; Bedford, R. B.; Scully, P. N. Tetrahedron Lett. 1998, 39, 9793. Peripalladated tri(1-naphthyl)phosphine catalysts: (c) Spescha, M.; Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361.
24. 6b,k
25. Review on cyclometalation: Ryabov, A. D. Chem. Rev. 1990, 90, 403.
26. Reviews on metalation by late transition metals: (a) Spencer, J.; Pfeffer, M. In Advances in Metal-Organic Chemistry, Liebeskind, L. S., Ed.; JAI Press: Stamford, 1998; Vol. 6, p 103. (b) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1985, 85, 245. (c) Sen, A. Acc. Chem. Res. 1985, 28, 154. (d) Murai, S.; Kakiuchi, F.; Sekine, S., Tanaka, Y.; Kakitani, A.; Sonoda, M.; Chatani, N. Pure Appl. Chem. 1994, 66, 1527.
27. Reviews on metalation by late transition metals: (a) Spencer, J.; Pfeffer, M. In Advances in Metal-Organic Chemistry, Liebeskind, L. S., Ed.; JAI Press: Stamford, 1998; Vol. 6, p 103. (b) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1985, 85, 245. (c) Sen, A. Acc. Chem. Res. 1985, 28, 154. (d) Murai, S.; Kakiuchi, F.; Sekine, S., Tanaka, Y.; Kakitani, A.; Sonoda, M.; Chatani, N. Pure Appl. Chem. 1994, 66, 1527.
28. Reviews on metalation by late transition metals: (a) Spencer, J.; Pfeffer, M. In Advances in Metal-Organic Chemistry, Liebeskind, L. S., Ed.; JAI Press: Stamford, 1998; Vol. 6, p 103. (b) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1985, 85, 245. (c) Sen, A. Acc. Chem. Res. 1985, 28, 154. (d) Murai, S.; Kakiuchi, F.; Sekine, S., Tanaka, Y.; Kakitani, A.; Sonoda, M.; Chatani, N. Pure Appl. Chem. 1994, 66, 1527.
29. Reviews on metalation by late transition metals: (a) Spencer, J.; Pfeffer, M. In Advances in Metal-Organic Chemistry, Liebeskind, L. S., Ed.; JAI Press: Stamford, 1998; Vol. 6, p 103. (b) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1985, 85, 245. (c) Sen, A. Acc. Chem. Res. 1985, 28, 154. (d) Murai, S.; Kakiuchi, F.; Sekine, S., Tanaka, Y.; Kakitani, A.; Sonoda, M.; Chatani, N. Pure Appl. Chem. 1994, 66, 1527.
30. Lead references on the mechanism of the metalation of arenes: (a) Vigalok, A.; Uzan, O.; Shimon, L. J. W.; Ben-David, Y.; Martin, J. M. L.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 12539. (b) Matsubara, T.; Koga, N.; Musaev, D.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 12692.
31. Lead references on the mechanism of the metalation of arenes: (a) Vigalok, A.; Uzan, O.; Shimon, L. J. W.; Ben-David, Y.; Martin, J. M. L.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 12539. (b) Matsubara, T.; Koga, N.; Musaev, D.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 12692.
32. Previous work of this group demonstrated that small variations on the metal complex could lead to complete regiocontrol in the palladation reactions: (a) Cárdenas, D. J.; Echavarren, A. M.; Vegas, A. Organometallics 1994, 13, 882. (b) Cárdenas, D. J.; Echavarren, A. M. Organometallics 1995, 14, 4427. See also: (c) Constable, A. G.; McDonald, W. S.; Sawkins, L. C.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1978, 1061. (d) Constable, A. G.; McDonald, W. S.; Sawkins, L. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 1992. (e) Galli, B.; Gasparrini, F.; Maresca, L.; Natile, G.; Palmieri, G. J. Chem. Soc., Dalton Trans. 1983, 1483, and references therein.
33. Previous work of this group demonstrated that small variations on the metal complex could lead to complete regiocontrol in the palladation reactions: (a) Cárdenas, D. J.; Echavarren, A. M.; Vegas, A. Organometallics 1994, 13, 882. (b) Cárdenas, D. J.; Echavarren, A. M. Organometallics 1995, 14, 4427. See also: (c) Constable, A. G.; McDonald, W. S.; Sawkins, L. C.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1978, 1061. (d) Constable, A. G.; McDonald, W. S.; Sawkins, L. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 1992. (e) Galli, B.; Gasparrini, F.; Maresca, L.; Natile, G.; Palmieri, G. J. Chem. Soc., Dalton Trans. 1983, 1483, and references therein.
34. Previous work of this group demonstrated that small variations on the metal complex could lead to complete regiocontrol in the palladation reactions: (a) Cárdenas, D. J.; Echavarren, A. M.; Vegas, A. Organometallics 1994, 13, 882. (b) Cárdenas, D. J.; Echavarren, A. M. Organometallics 1995, 14, 4427. See also: (c) Constable, A. G.; McDonald, W. S.; Sawkins, L. C.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1978, 1061. (d) Constable, A. G.; McDonald, W. S.; Sawkins, L. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 1992. (e) Galli, B.; Gasparrini, F.; Maresca, L.; Natile, G.; Palmieri, G. J. Chem. Soc., Dalton Trans. 1983, 1483, and references therein.
35. Previous work of this group demonstrated that small variations on the metal complex could lead to complete regiocontrol in the palladation reactions: (a) Cárdenas, D. J.; Echavarren, A. M.; Vegas, A. Organometallics 1994, 13, 882. (b) Cárdenas, D. J.; Echavarren, A. M. Organometallics 1995, 14, 4427. See also: (c) Constable, A. G.; McDonald, W. S.; Sawkins, L. C.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1978, 1061. (d) Constable, A. G.; McDonald, W. S.; Sawkins, L. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 1992. (e) Galli, B.; Gasparrini, F.; Maresca, L.; Natile, G.; Palmieri, G. J. Chem. Soc., Dalton Trans. 1983, 1483, and references therein.
36. Previous work of this group demonstrated that small variations on the metal complex could lead to complete regiocontrol in the palladation reactions: (a) Cárdenas, D. J.; Echavarren, A. M.; Vegas, A. Organometallics 1994, 13, 882. (b) Cárdenas, D. J.; Echavarren, A. M. Organometallics 1995, 14, 4427. See also: (c) Constable, A. G.; McDonald, W. S.; Sawkins, L. C.; Shaw, B. L. J. Chem. Soc., Chem. Commun. 1978, 1061. (d) Constable, A. G.; McDonald, W. S.; Sawkins, L. C.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 1992. (e) Galli, B.; Gasparrini, F.; Maresca, L.; Natile, G.; Palmieri, G. J. Chem. Soc., Dalton Trans. 1983, 1483, and references therein.
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