Intramolecular nucleophilic addition of vinylpalladiums to aryl ketones [9]

Journal of the American Chemical Society

Volumn 121, Issue 14, 1999, Pages 3545-3546

  Quan, Long Guo ^a   Gevorgyan, Vladimir ^a,b   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG; VINYL PALLADIUM;

CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; LETTER;

EID: 0001605581     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983645w     Document Type: Letter

References (48)

1. For recent reviews, see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (b) Tsuji, J. In Palladium Reagents and Catalysts; John Wiley: Chichester, 1995. (c) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Uu, F. Chem. Rev. 1996, 96, 365. (d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
2. For recent reviews, see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (b) Tsuji, J. In Palladium Reagents and Catalysts; John Wiley: Chichester, 1995. (c) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Uu, F. Chem. Rev. 1996, 96, 365. (d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
3. For recent reviews, see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (b) Tsuji, J. In Palladium Reagents and Catalysts; John Wiley: Chichester, 1995. (c) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Uu, F. Chem. Rev. 1996, 96, 365. (d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
4. For recent reviews, see: (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. In Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987. (b) Tsuji, J. In Palladium Reagents and Catalysts; John Wiley: Chichester, 1995. (c) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.-Y.; Uu, F. Chem. Rev. 1996, 96, 365. (d) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
5. For reviews, see for example: (a) Trost, B. M. Acc. Chem. Res. 1980, 13, 2615. (b) Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: New York, 1980. (c) Trost, B. M. Pure Appl. Chem. 1981, 53, 2357. (d) Tsuji, J. Pure Appl. Chem. 1982, 54, 197. For asymmetric palladium-catalyzed allylic alkylation, see: (e) Trost, B.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
6. For reviews, see for example: (a) Trost, B. M. Acc. Chem. Res. 1980, 13, 2615. (b) Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: New York, 1980. (c) Trost, B. M. Pure Appl. Chem. 1981, 53, 2357. (d) Tsuji, J. Pure Appl. Chem. 1982, 54, 197. For asymmetric palladium-catalyzed allylic alkylation, see: (e) Trost, B.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
7. For reviews, see for example: (a) Trost, B. M. Acc. Chem. Res. 1980, 13, 2615. (b) Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: New York, 1980. (c) Trost, B. M. Pure Appl. Chem. 1981, 53, 2357. (d) Tsuji, J. Pure Appl. Chem. 1982, 54, 197. For asymmetric palladium-catalyzed allylic alkylation, see: (e) Trost, B.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
8. For reviews, see for example: (a) Trost, B. M. Acc. Chem. Res. 1980, 13, 2615. (b) Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: New York, 1980. (c) Trost, B. M. Pure Appl. Chem. 1981, 53, 2357. (d) Tsuji, J. Pure Appl. Chem. 1982, 54, 197. For asymmetric palladium-catalyzed allylic alkylation, see: (e) Trost, B.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
9. For reviews, see for example: (a) Trost, B. M. Acc. Chem. Res. 1980, 13, 2615. (b) Tsuji, J. Organic Synthesis with Palladium Compounds; Springer-Verlag: New York, 1980. (c) Trost, B. M. Pure Appl. Chem. 1981, 53, 2357. (d) Tsuji, J. Pure Appl. Chem. 1982, 54, 197. For asymmetric palladium-catalyzed allylic alkylation, see: (e) Trost, B.; Vranken, D. L. V. Chem. Rev. 1996, 96, 395.
10. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
11. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
12. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
13. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
14. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
15. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
16. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
17. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
18. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
19. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
20. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
21. For allylpalladium species involved in the reactions with electrophiles, see: (a) Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835. (b) Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1196. (c) Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3704. (d) Qiu, W.; Wang, Z. J. Chem. Soc., Chem. Commun. 1989, 356. (e) Zhang, P.; Zhang, W.; Zhang, T.; Wang, T.; Zhou, W. J. Chem. Soc., Chem. Commun. 1991, 491. (f) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 1195. (g) Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215. (h) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett. 1991, 32, 225. For nucleophilic bis-π-allylpalladium complexes, see: (i) Nakamura, H.; Asao, N.; Yamamoto, J. Chem. Soc., Chem. Commun. 1995, 1273. (j) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1459. (k) Nakamura, H.; Iwama, H.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 6641. On the nucleophilic nature of palladium-trimethylenemethane complexes, see for example: (l) Trost, B. M.; King, S. A. J. Am. Chem. Soc. 1990, 112, 408 and references therein.
22. On the stoichiometric amphiphilic π-allylpalladium complexes, see: Hegedus, L. S.; Åkermark, B.; Olsten, D. J.; Anderson, O. P.; Zetterberg, K. J. Am. Chem. Soc. 1982, 104, 697. For the amphiphilic bis-π-allylpalladium complexes formed catalytically, see: Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113.
23. On the stoichiometric amphiphilic π-allylpalladium complexes, see: Hegedus, L. S.; Åkermark, B.; Olsten, D. J.; Anderson, O. P.; Zetterberg, K. J. Am. Chem. Soc. 1982, 104, 697. For the amphiphilic bis-π-allylpalladium complexes formed catalytically, see: Nakamura, H.; Shim, J.-G.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8113.
24. For reviews on Heck reaction, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4. For vinylpalladation of alkynes and alkenes, see also ref 1c and references therein.
25. For reviews on Heck reaction, see: (a) Heck, R. F. Acc. Chem. Res. 1979, 12, 146. (b) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4. For vinylpalladation of alkynes and alkenes, see also ref 1c and references therein.
26. (a) Wu, G.; Rheingold, A. L.; Geib, S. J.; Heck, R. F. Organometallics 1987, 6, 1941.
27. (b) Larock, R. C.; Doty, M. J.; Tian, Q.; Zenner, J. M. J. Org. Chem. 1997, 62, 7536.
28. (c) Merlic, C. A.; McInnes, D. M. Tetrahedron Lett. 1997, 38, 7661.
29. (d) Dyker, G.; Kellner, A. Tetrahedron Lett. 1994, 35, 7633.
30. (e) Grigg, R.; Loganathan, V.; Sridharan, V. Tetrahedron Lett. 1996, 37, 3399.
31. (f) Larock, R. C.; Tian, Q. J. Org. Chem. 1998, 63, 2002.
32. (g) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org. Chem. 1993, 58, 4579.
33. (a) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
34. (b) Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270.
35. "Insertion" term was used based upon the proposed mechanisms of the authors. However, the overall-transformation is clearly a "substitution reaction."
36. 1RRC=O) were obtained. See, for example: (a) Tao, W.; Silverberg, L. J.; Rheingold, A. L.; Heck, R. F. Organometallics 1989, 8, 2550. (b) Larock, R. C.; Han, X, Doty, M. J. Tetrahedron Lett. 1998, 59, 5713. See also refs 6f,g, and 7b.
37. 1RRC=O) were obtained. See, for example: (a) Tao, W.; Silverberg, L. J.; Rheingold, A. L.; Heck, R. F. Organometallics 1989, 8, 2550. (b) Larock, R. C.; Han, X, Doty, M. J. Tetrahedron Lett. 1998, 59, 5713. See also refs 6f,g, and 7b.
38. Synthesis of indenols via coupling of aromatic organomanganese compounds with alkynes is known. See: Liebeskind, L. S.; Gasdaska, J. R.; McCallum, J. S. J. Org. Chem. 1989, 54, 669.
39. 3 also catalyzed this reaction; however, the yields of 3a in these cases were somewhat lower.
40. 3 was found to be not effective at all as a base in the mentioned reaction.
41. Although the conditions of the methods B and C were the best for the carbocyclization of most of the ketones tested, the employment of the conditions A still gave the better yields for the reactions of 1a with 2a and 2b (Table 1, entries 1,2).
42. As expected, this reaction is limited to the use of internal alkynes only. Thus, terminal alkyne, 1-octyne, did not undergo the vinylpalladation with 1a,c; instead, the corresponding Sonogashira coupling products were obtained.
43. Iodides also underwent similar reactions; however, the yields of indenols in these cases were somewhat lower.
44. It is well-known that carbopalladation of unsymmetrical alkynes proceeds in the syn-fashion producing a vinylpalladium species in which the carbon atom is attached to the less hindered site and, consequently palladium attached to the most hindered terminus of alkyne. See, for example ref 6f and references therein.
45. 4 (1e) were 4, 16, and > 120 h, correspondingly. Although the so-called "half-reaction time" data are very approximate, they are useful for the rough estimation of relative reactivities. For example, see: Fleming, I.; Langley, J. A. J. Chem. Soc., Perkin. Trans, 1 1981, 1412.
46. It is well-known that the rates of nucleophilic addition to a keto group are enhanced by the electron-withdrawing groups at the keto function and reduced by the electron-donating ones. For reviews on addition of C-nucleophiles, see for example: (a) Roush, W. R. In Comprehesive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; VoL 1, Chapter 1.1. (b) Fleming, I. In Comprehesive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Chapter 2.2. (c) Stowell, J. C. In Carbanions in Organic Synthesis; John Wiley: New York, 1980.
47. It is well-known that the rates of nucleophilic addition to a keto group are enhanced by the electron-withdrawing groups at the keto function and reduced by the electron-donating ones. For reviews on addition of C-nucleophiles, see for example: (a) Roush, W. R. In Comprehesive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; VoL 1, Chapter 1.1. (b) Fleming, I. In Comprehesive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Chapter 2.2. (c) Stowell, J. C. In Carbanions in Organic Synthesis; John Wiley: New York, 1980.
48. It is well-known that the rates of nucleophilic addition to a keto group are enhanced by the electron-withdrawing groups at the keto function and reduced by the electron-donating ones. For reviews on addition of C-nucleophiles, see for example: (a) Roush, W. R. In Comprehesive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; VoL 1, Chapter 1.1. (b) Fleming, I. In Comprehesive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Chapter 2.2. (c) Stowell, J. C. In Carbanions in Organic Synthesis; John Wiley: New York, 1980.