"Walking" of the C-C π bond over long distances in Pd-catalyzed reactions of 2,3-allenoic acids with ω-1-alkenyl halides

Angewandte Chemie - International Edition

Volumn 42, Issue 17, 2003, Pages 1955-1957

  Ma, Shengming ^a   Yu, Zhanqian ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Alkenes; Allenes; Carboxylic acids; Lactones; Migration; Oxypalladation

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; PALLADIUM;

CYCLIZATION;

CHEMICAL BONDS;

4 PHENYL 2 PROPYL 2,3 BUTADIENOIC ACID; CARBON; HALIDE; HOMOALLYL BROMIDE; METAL COMPLEX; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION;

EID: 0038215536     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250562     Document Type: Article

References (33)

1. a) S. Ma, Youji Huaxue 1991, 11, 561.
2. b) A. de Meijere, F. E. Mever, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
3. b) A. de Meijere, F. E. Mever, Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
4. c) E. Negishi, C. Coperet, S. Ma, S. Liou, F. Liu, Chem. Rev. 1996, 96, 365.
5. d) I. Ojima, M. Tzamarioudaki, Z. Li, R. J. Donovan, Chem. Rev. 1996, 96, 635.
6. a) Palladium Reagents in Organic Synthesis (Ed.: R. F. Heck), Academic Press, London, 1985.
7. b) Palladium Reagents and Catalysts: Innovations in Organic Synthesis (Eds.: J. Tsuji), Wiley, Chichester, UK, 1995.
8. c) Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, New York, 1998.
9. a) T. Mizoroki, K. Mori, A. Ozaki, Bull. Chem. Soc. Jpn. 1971, 44, 581.
10. b) R. F. Heck, J. P. Nolley, J. Org. Chem. 1972, 37, 2320.
11. c) G. D. Daves, A. Hallberg, Chem. Rev. 1989, 89, 1433.
12. d) G. T. Crisp, Chem. Soc. Rev. 1998, 27, 427.
13. e) I. P. Beletskaya, A. V. Cheprakov, Chem. Rev. 2000, 100, 3009.
14. a) S. Ma, X. Lu, J. Chem. Soc. Chem. Commun. 1990, 733.
15. b) S. Ma, X. Lu, J. Org. Chem. 1991, 56, 5120.
16. c) X. Lu, G. Zhu, Z. Wang, Synlett 1998, 115.
17. d) Q. Zhang, X. Lu, J. Am. Chem. Soc. 2000, 122, 7604.
18. For the synthesis of butenolides from 2,3-allenoic acids, see: a) S. Ma, Z. Shi, J. Org. Chem. 1998, 63, 6387. b) S. Ma, Z. Yu, Angew. Chem. 2002, 114, 1853; Angew. Chem. Int. Ed. 2002, 41, 1775.
19. For the synthesis of butenolides from 2,3-allenoic acids, see: a) S. Ma, Z. Shi, J. Org. Chem. 1998, 63, 6387. b) S. Ma, Z. Yu, Angew. Chem. 2002, 114, 1853; Angew. Chem. Int. Ed. 2002, 41, 1775.
20. For the synthesis of butenolides from 2,3-allenoic acids, see: a) S. Ma, Z. Shi, J. Org. Chem. 1998, 63, 6387. b) S. Ma, Z. Yu, Angew. Chem. 2002, 114, 1853; Angew. Chem. Int. Ed. 2002, 41, 1775.
21. a) S. Ma, L. Li, Org. Lett. 2000, 2, 941.
22. b) S. Ma, W. Gao, Tetrahedron Lett. 2000, 41, 8933.
23. c) S. Ma, W. Gao, J. Org. Chem. 2002, 67, 6104.
24. A. J. Canty, Acc. Chem. Res. 1992, 25, 83.
25. a) H. O. House, W. C. Liang, P. D. Weeks, J. Org. Chem. 1974, 39, 3102.
26. b) E. Negishi, L. D. Boardman, H. Sawada, V. Bagheri, A. T. Stoll, J. M. Tour, C. L. Rand, J. Am. Chem. Soc. 1988, 110, 5383.
27. c) S. Xu, S. J. N. Cruchon-Dupeyrat, J. C. Garno, G. Liu, G. K. Jennings, T. Yong, P. E. Laibinis, J. Chem. Phys. 1998, 108, 5002.
28. d) U. Beginn, G. Zipp, M. Moller, Chem. Eur. J. 2000, 6, 2016.
29. e) K. Chai, P. Sampson, J. Org. Chem. 1993, 58, 6807.
30. a) D. D. Bender, F. G. Stakem, R. F. Heck, J. Org. Chem. 1982, 47, 1278.
31. b) B. C. Soderberg, B. Akermark, S. S. Hall, J. Org. Chem. 1988, 53, 2925.
32. c) A. C. Albeniz, P. Espinet, Y. Jeannin, M. Philoche-Levisalles, B. E. Mann, J. Am. Chem. Soc. 1990, 112, 6594.
33. d) R. C. Larock, Y. Lu, A. C. Bain, J. Org. Chem. 1991, 56, 4589.