Water enables direct use of allyl alcohol for Tsuji-Trost reaction without activators

Organic Letters

Volumn 6, Issue 22, 2004, Pages 4085-4088

  Kinoshita, Hidenori ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; AMINE; PALLADIUM COMPLEX; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; HYDRATION; MATHEMATICAL COMPUTING; THEORETICAL MODEL;

EID: 8744239436     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048207a     Document Type: Article

References (37)

1. (a) Lu, X.; Jiang, X.; Tao, X. J. Organomet. Chem. 1988, 344, 109.
2. (b) Satoh, I.; Ikeda, M.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4877.
3. (c) Tamaru, Y.; Horino, Y.; Araki, M.; Tanaka, S.; Kimura, M. Tetrahedron Lett. 2000, 41, 5705.
4. (d) Stary, J.; Stara, I. G.; Kocovsky, P. Tetrahedron 1993, 34, 179.
5. (e) Lumin, S.; Falck, J. R.; Capdevila, J.; Karara, A. Tetrahedron Lett. 1992, 33, 2091.
6. (f) Sakamoto, M.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1996, 69, 1065.
7. (g) Patil, N. T.; Yamamoto, Y. Tetrahedron Lett. 2004, 45, 3101.
8. (a) Ozawa, F.; Okamoto, H.; Kawagishi, S.; Yamamoto, S.; Minami, T.; Yoshifuji, M. J. Am. Chem. Soc. 2002, 124, 10968.
9. (b) Kayaki, Y.; Koda, T.; Ikariya, T. J. Org. Chem. 2004, 69, 2595.
10. (a) Safi, M.; Sinou, D. Tetrahedron Lett. 1991, 32, 2025.
11. (b) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715.
12. (c) Blart, E.; Genêt, J. P.; Safi, M.; Savignac, M.; Sinou, D. Tetrahedron 1994, 50, 505.
13. (d) Kobayashi, S.; Lam, W. W.-L.; Manabe, K. Tetrahedron Lett. 2000, 41, 6115.
14. (e) Danjo, H.; Tanaka, D.; Hayashi, T.; Uozumi, Y. Tetrahedron 1999, 55 14341,
15. (f) Uozumi, Y.; Shibatomi, K. J. Am. Chem. Soc. 2001, 123, 2919.
16. (g) Bergbreiter, D. E.; Liu, Y.-S. Tetrahedron Lett. 1997, 38, 7843.
17. Recently, Kobayashi has reported allylation in aqueous media with a carboxylic acid as an activator. Manabe, K.; Kobayashi, S. Org. Lett. 2003, 5, 3241.
18. See the Supporting Information.
19. 2O - water biphasic system provided 3b in 53% yield under otherwise identical conditions as entry 2 in Table 1.
20. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
21. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
22. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
23. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
24. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
25. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
26. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
27. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
28. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
29. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
30. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
31. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
32. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
33. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
34. For theoretical calculations involving π-allylpalladium, see: (a) Delbecq, F.; Lapouge, C. Organometallics 2000, 19, 2716. (b) Branchadell, V.; Moreno-Manas, M.; Pleixats, R. Organometallics 2002, 21, 2407. (c) Solin, N.; Szabó, K. J. Organometallics 2001, 20, 5464. (d) Szabó, K. J. Chem. Eur. J. 1997, 3, 592. (e) Szabó, K. J. Chem. Eur. J. 2000, 6, 4413. (f) Solin, N.; Narayan, S.; Szabó, K. J. J. Org. Chem. 2001, 66, 1686. (g) Szabó, K. J.; Hupe, E.; Larsson, A. L. E. Organometallics 1997, 16, 3779. (h) Szabó,K. J. Organometallics 1996, 15, 1128. (i) Szabó, K. J. J. Am. Chem. Soc. 1996, 118. 7818. (j) Sakaki, S.; Takeuchi, K.; Sugimoto, M.; Kurosawa, H. Organometallics 1997, 16, 2995. (k) Sakaki, S.; Satoh, H.; Shono, H.; Ujino, Y. Organometallics 1996, 15, 1713. (l) Biswas, B.; Sugimoto, M.; Sakaki, S. Organometallics 1999, 18, 4015. (m) Branchadell, V.; Moreno-Mañas, M.; Pajuelo, F.; Pleixats, R. Organometallics 1999, 18, 4934; (n) Hagelin, H.; Åkermark, B.; Norrby, P.-O. Chem. Eur. J. 1999, 5, 902; (m) Dedieu, A. Chem. Rev. 2000, 100, 543.
35. Optimization with the PCM method failed to converge.
36. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43.
37. π-Allylpalladium (AP) is stabilized in water by 18.4 kcal/mol from its optimized structure in a vacuum (B3LYP/BS1), whereas the Pd(0) - olefin complex (PC) is destabilized by 14.3 kcal/mol. This can be one of the driving forces.