Controlled double-bond migration in palladium-catalyzed intramolecular arylation of enamidines

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7147-7155

  Ripa, Lena ^a   Hallberg, Anders ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0039334441     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960970y     Document Type: Article

References (85)

1. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
2. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
3. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
4. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
5. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
6. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
7. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
8. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
9. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
10. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
11. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
12. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
13. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
14. For palladium-catalyzed Heck arylation of cyclic enol ethers, see: (a) Andersson, C.-M.; Hallberg, A.; Daves, G. D., Jr. J. Org. Chem. 1987, 52, 3529-3536. (b) Arai, I.; Daves, G. D., Jr. J. Org. Chem. 1979, 44, 21-23. (c) Genêt, J. P.; Blart, E.; Savignac, M. Synlett 1992, 715-717. (d) Hillers, S.; Reiser, O. Synlett 1995, 153-154. (e) Hillers, S.; Sartori, S.; Reiser, O. J. Am. Chem. Soc. 1996, 118, 2087-2088. (f) Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603-2606. (g) Larock, R. C.; Gong, W. H. J. Org. Chem. 1990, 55, 407-408. For examples of chiral induction in Heck arylation of cyclic enol ethers, see: (h) Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem. 1992, 64, 421-427. (i) Hillers, S.; Reiser, O. Tetrahedron Lett. 1993, 34, 5265-5268. (j) Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 200-202. (k) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417-1419. (l) Ozawa, F.; Kubo, A.; Hayashi, T. Tetrahedron Lett. 1992, 33, 1485-1488. (m) Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K.-i. Organometallics 1993, 12, 4188-4196. (n) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845-6848.
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23. For first examples of the use of Heck arylation for construction of tetrasubstituted carbon centers see: (a) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. (b) Grigg, R.; Sridharan, V.; Stevenson, P.; Worakun, T. J. Chem. Soc., Chem. Commun. 1986, 1697-1699. For recent examples including asymmetric induction, see: (c) Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1995, 60, 4322-4323. (d) Kondo, K.; Sodeoka, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 2453-2464. (e) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423-1430. (f) Takemoto, T.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477-8478.
24. For first examples of the use of Heck arylation for construction of tetrasubstituted carbon centers see: (a) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. (b) Grigg, R.; Sridharan, V.; Stevenson, P.; Worakun, T. J. Chem. Soc., Chem. Commun. 1986, 1697-1699. For recent examples including asymmetric induction, see: (c) Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1995, 60, 4322-4323. (d) Kondo, K.; Sodeoka, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 2453-2464. (e) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423-1430. (f) Takemoto, T.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477-8478.
25. For first examples of the use of Heck arylation for construction of tetrasubstituted carbon centers see: (a) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. (b) Grigg, R.; Sridharan, V.; Stevenson, P.; Worakun, T. J. Chem. Soc., Chem. Commun. 1986, 1697-1699. For recent examples including asymmetric induction, see: (c) Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1995, 60, 4322-4323. (d) Kondo, K.; Sodeoka, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 2453-2464. (e) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423-1430. (f) Takemoto, T.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477-8478.
26. For first examples of the use of Heck arylation for construction of tetrasubstituted carbon centers see: (a) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. (b) Grigg, R.; Sridharan, V.; Stevenson, P.; Worakun, T. J. Chem. Soc., Chem. Commun. 1986, 1697-1699. For recent examples including asymmetric induction, see: (c) Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1995, 60, 4322-4323. (d) Kondo, K.; Sodeoka, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 2453-2464. (e) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423-1430. (f) Takemoto, T.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477-8478.
27. For first examples of the use of Heck arylation for construction of tetrasubstituted carbon centers see: (a) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. (b) Grigg, R.; Sridharan, V.; Stevenson, P.; Worakun, T. J. Chem. Soc., Chem. Commun. 1986, 1697-1699. For recent examples including asymmetric induction, see: (c) Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1995, 60, 4322-4323. (d) Kondo, K.; Sodeoka, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 2453-2464. (e) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423-1430. (f) Takemoto, T.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477-8478.
28. For first examples of the use of Heck arylation for construction of tetrasubstituted carbon centers see: (a) Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130-4133. (b) Grigg, R.; Sridharan, V.; Stevenson, P.; Worakun, T. J. Chem. Soc., Chem. Commun. 1986, 1697-1699. For recent examples including asymmetric induction, see: (c) Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1995, 60, 4322-4323. (d) Kondo, K.; Sodeoka, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 2453-2464. (e) Overman, L. E. Pure Appl. Chem. 1994, 66, 1423-1430. (f) Takemoto, T.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477-8478.
29. (a) Andersson, C.-M.; Larsson, J.; Hallberg, A. J. Org. Chem. 1990, 55, 5757-5761.
30. (b) Larhed, M.; Andersson, C.-M.; Hallberg, A. Tetrahedron 1994, 50, 285-304. See also:
31. (c) Nilsson, K.; Hallberg, A. J. Org. Chem. 1992, 57, 4015-4017.
32. a = 10-11, Häfelinger, G.; Kuske, F. K. H. In The chemistry of amidines and imidates; Patai, S., Rappoport, Z., Ed.; John Wiley & Sons: 1991; Vol. 2, pp 75-80.
33. See, for example: Grove, D. M.; van Koten, G.; Ubbels, H. J. C.; Vrieze, K.; Niemann, L. C.; Stam, C. H. J. Chem. Soc., Dalton Trans. 1986, 717-724.
34. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
35. Meyers, A. I.; Edwards, P. D.; Rieker, W. F.; Bailey, T. R. J. Am. Chem. Soc. 1984, 106, 3270-3276.
36. The proton sponge was 1,8-bis(dimethylamino)naphthalene: Alder, R. W.; Bowman, P. S.; Steele, W. R. S.; Winterman, D. R. Chem. Commun. 1968, 723-724.
37. For use of triphenylarsine in the Heck reaction, see: (a) Zhang, H.-C.; Daves, G. D., Jr. J. Org. Chem. 1992, 57, 4690-4696. (b) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500.
38. For use of triphenylarsine in the Heck reaction, see: (a) Zhang, H.-C.; Daves, G. D., Jr. J. Org. Chem. 1992, 57, 4690-4696. (b) Zhang, H.-C.; Daves, G. D., Jr. Organometallics 1993, 12, 1499-1500.
39. 2, 0.01 mmol of bidentate ligand or 0.02 mmol of monodentate ligand, 0.20 mmol of triethylamine, and 0.10 mmol of naphthalene (as internal standard). The reaction mixture was heated under Ar in a sealed tube at 80°C for 12-96 h. The product composition was monitored by GC-MS.
40. BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl: Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350.
41. DPPF = 1,1′-bis(diphenylphosphino)ferrocene; DPPB = 1,4-bis(diphenylphosphino)butane; DPPP = 1,3-bis(diphenylphosphino(propane; DPPE = 1,2-bis(diphenylphosphino)ethane; DPPM = bis(diphenylphosphino)methane
42. 3 = triphenylarsine, TFP = tri-2-furylphosphine
43. Sato, Y.; Sodoeka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738-4739.
44. Dihydospiropyridine 5a was cleaved with hydrazine, and the resulting secondary amine was analyzed on a chiral GLC-column, heptakis(6-O-(tert-butyldimethylsilyl)-2,3-di-O-metriyl-β-cyclodextrin, prepared and developed by Prof. W. A. König. Institut für Organische Chemie, Universität Hamburg, D-201 46 Hamburg, Germany.
45. The beneficial effect of silver additives in controlling double-bond isomerization in the Heck reaction was first observed by Overman's group. (a) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328-2329 and ref 5a. Use of silver for controlling double-bond isomerization in heterocycles. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050 and refs 1f,g,n, 2a, and 6c. For the first use of silver salts in the Heck reaction, see: (c) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896-3900. Silver salts have also been reported to have a beneficial effect in the asymmetric Heck reaction. (d) Sato, Y.; Sodoeke, M.; Shibasaki, M. Chem. Lett. 1990, 1953-1954. (e) Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371-382.
46. The beneficial effect of silver additives in controlling double-bond isomerization in the Heck reaction was first observed by Overman's group. (a) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328-2329 and ref 5a. Use of silver for controlling double-bond isomerization in heterocycles. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050 and refs 1f,g,n, 2a, and 6c. For the first use of silver salts in the Heck reaction, see: (c) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896-3900. Silver salts have also been reported to have a beneficial effect in the asymmetric Heck reaction. (d) Sato, Y.; Sodoeke, M.; Shibasaki, M. Chem. Lett. 1990, 1953-1954. (e) Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371-382.
47. The beneficial effect of silver additives in controlling double-bond isomerization in the Heck reaction was first observed by Overman's group. (a) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328-2329 and ref 5a. Use of silver for controlling double-bond isomerization in heterocycles. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050 and refs 1f,g,n, 2a, and 6c. For the first use of silver salts in the Heck reaction, see: (c) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896-3900. Silver salts have also been reported to have a beneficial effect in the asymmetric Heck reaction. (d) Sato, Y.; Sodoeke, M.; Shibasaki, M. Chem. Lett. 1990, 1953-1954. (e) Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371-382.
48. The beneficial effect of silver additives in controlling double-bond isomerization in the Heck reaction was first observed by Overman's group. (a) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328-2329 and ref 5a. Use of silver for controlling double-bond isomerization in heterocycles. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050 and refs 1f,g,n, 2a, and 6c. For the first use of silver salts in the Heck reaction, see: (c) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896-3900. Silver salts have also been reported to have a beneficial effect in the asymmetric Heck reaction. (d) Sato, Y.; Sodoeke, M.; Shibasaki, M. Chem. Lett. 1990, 1953-1954. (e) Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371-382.
49. The beneficial effect of silver additives in controlling double-bond isomerization in the Heck reaction was first observed by Overman's group. (a) Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328-2329 and ref 5a. Use of silver for controlling double-bond isomerization in heterocycles. (b) Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047-2050 and refs 1f,g,n, 2a, and 6c. For the first use of silver salts in the Heck reaction, see: (c) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896-3900. Silver salts have also been reported to have a beneficial effect in the asymmetric Heck reaction. (d) Sato, Y.; Sodoeke, M.; Shibasaki, M. Chem. Lett. 1990, 1953-1954. (e) Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50, 371-382.
50. Grigg, R.; Loganathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687-690.
51. (a) Larock, R. C.; Baker, B. E. Tetrahedron Lett. 1988, 29, 905-908.
52. (b) Laschat, S.; Narjes, F.; Overman, L. E. Tetrahedron 1994, 50, 347-358 and ref 1m.
53. The counter anion of the silver salts has been shown to play a significant role in the asymmetric Heck reaction. Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 4965-4968 and refs 19d,e.
54. The amidines were converted to the corresponding formyl compounds by hydrolysis with KOH in MeOH/water and analyzed with a chiral GLC-column, Heptakis(6-O-(tert-butyldimethylsilyl))-2,3-di-O-methyl-β-cyclodextrin, prepared and developed by Prof. W. A. König. Institut für Organische Chemie, Universität Hamburg, D-201 46 Hamburg, Germany.
55. (a) Meyers, A. I.; Edwards, P. D.; Bailey, T. R.; Jagdmann, G. E. J. J. Org. Chem. 1986, 50, 1019-1026. See also:
56. (b) Beak, P.; Lee, W. K. J. Org. Chem. 1993, 58, 1109-1117.
57. For olefin as reducing agent, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. For amine as reducing agent see: (b) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571-572. For phosphine as reducing agent, see: (c) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009-3013. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818-1826. (e) Mandai, T.; Matsumoto, T.; Tsuji, J. Tetrahedron Lett. 1993, 34, 2513-2516. (f) Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177-2180.
58. For olefin as reducing agent, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. For amine as reducing agent see: (b) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571-572. For phosphine as reducing agent, see: (c) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009-3013. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818-1826. (e) Mandai, T.; Matsumoto, T.; Tsuji, J. Tetrahedron Lett. 1993, 34, 2513-2516. (f) Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177-2180.
59. For olefin as reducing agent, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. For amine as reducing agent see: (b) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571-572. For phosphine as reducing agent, see: (c) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009-3013. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818-1826. (e) Mandai, T.; Matsumoto, T.; Tsuji, J. Tetrahedron Lett. 1993, 34, 2513-2516. (f) Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177-2180.
60. For olefin as reducing agent, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. For amine as reducing agent see: (b) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571-572. For phosphine as reducing agent, see: (c) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009-3013. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818-1826. (e) Mandai, T.; Matsumoto, T.; Tsuji, J. Tetrahedron Lett. 1993, 34, 2513-2516. (f) Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177-2180.
61. For olefin as reducing agent, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. For amine as reducing agent see: (b) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571-572. For phosphine as reducing agent, see: (c) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009-3013. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818-1826. (e) Mandai, T.; Matsumoto, T.; Tsuji, J. Tetrahedron Lett. 1993, 34, 2513-2516. (f) Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177-2180.
62. For olefin as reducing agent, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143-1145. For amine as reducing agent see: (b) McCrindle, R.; Ferguson, G.; Arsenault, G. J.; McAlees, A. J. J. Chem. Soc., Chem. Commun. 1983, 571-572. For phosphine as reducing agent, see: (c) Amatore, C.; Jutand, A.; M'Barki, M. A. Organometallics 1992, 11, 3009-3013. (d) Amatore, C.; Carré, E.; Jutand, A.; M'Barki, M. A. Organometallics 1995, 14, 1818-1826. (e) Mandai, T.; Matsumoto, T.; Tsuji, J. Tetrahedron Lett. 1993, 34, 2513-2516. (f) Ozawa, F.; Kubo, A.; Hayashi, T. Chem. Lett. 1992, 2177-2180.
63. Aryl iodides are known to react without phosphine ligands: Heck, R. F. Acc. Chem. Res. 1979, 12, 146-151.
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69. See ref 19e. Other examples where one of the two phosphine ligands in a bidentate ligand is displaced by the olefin prior to insertion. (a) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796-5800. (b) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481-1486. (c) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558-3563. (d) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.
70. See ref 19e. Other examples where one of the two phosphine ligands in a bidentate ligand is displaced by the olefin prior to insertion. (a) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796-5800. (b) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481-1486. (c) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558-3563. (d) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.
71. See ref 19e. Other examples where one of the two phosphine ligands in a bidentate ligand is displaced by the olefin prior to insertion. (a) Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem. 1991, 56, 5796-5800. (b) Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem. 1992, 57, 1481-1486. (c) Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558-3563. (d) Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158-163.
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