Mild α-halogenation reactions of 1,3-dicarbonyl compounds catalyzed by Lewis acids

Journal of Organic Chemistry

Volumn 67, Issue 21, 2002, Pages 7429-7431

  Yang, Dan ^a   Yan, Yi Long ^a   Lui, Bob ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHLORINATION; ESTERS;

BROMINATION;

HALOGENATION;

ACETIC ACID ETHYL ESTER; ACETONITRILE; CARBONYL DERIVATIVE; LEWIS ACID; MAGNESIUM PERCHLORATE; N BROMOSUCCINIMIDE;

ARTICLE; BROMINATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHLORINATION; HALOGENATION; IODINATION;

EID: 0037131155     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026025t     Document Type: Article

References (48)

1. Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; VCH Publishers Inc.: New York, 1999; pp 715-719.
2. For examples of α-bromo 1,3-dicarbonyl compounds in organic transformations, see: (a) Misra, A. P.; Raj, K.; Bhaduri; A. P. Synth. Commun. 1999, 29, 3227-3236. (b) Coats, S. J.; Wasserman, H. H. Tetrahedron Lett. 1995, 36, 7735-7738. (c) Endo, M.; Droghini, R. Can. J. Chem. 1988, 66, 1400-1404. (d) Hlavka, J.; Bitha, P.; Lin, Y.; Strohmeyer, T. J. Heterocycl. Chem. 1985, 22, 1317-1322. (e) Yoshida, J.; Yano, S.; Ozawa, T.; Kawabata, N. Tetrahedron Lett. 1984, 25, 2817-2820. (f) Kaye, P. T.; Meakins, G. D.; Smith, A. K.; Tirel, M. D. J. Chem. Soc., Perkin Trans. 1 1983, 1677-1680.
3. For examples of α-bromo 1,3-dicarbonyl compounds in organic transformations, see: (a) Misra, A. P.; Raj, K.; Bhaduri; A. P. Synth. Commun. 1999, 29, 3227-3236. (b) Coats, S. J.; Wasserman, H. H. Tetrahedron Lett. 1995, 36, 7735-7738. (c) Endo, M.; Droghini, R. Can. J. Chem. 1988, 66, 1400-1404. (d) Hlavka, J.; Bitha, P.; Lin, Y.; Strohmeyer, T. J. Heterocycl. Chem. 1985, 22, 1317-1322. (e) Yoshida, J.; Yano, S.; Ozawa, T.; Kawabata, N. Tetrahedron Lett. 1984, 25, 2817-2820. (f) Kaye, P. T.; Meakins, G. D.; Smith, A. K.; Tirel, M. D. J. Chem. Soc., Perkin Trans. 1 1983, 1677-1680.
4. For examples of α-bromo 1,3-dicarbonyl compounds in organic transformations, see: (a) Misra, A. P.; Raj, K.; Bhaduri; A. P. Synth. Commun. 1999, 29, 3227-3236. (b) Coats, S. J.; Wasserman, H. H. Tetrahedron Lett. 1995, 36, 7735-7738. (c) Endo, M.; Droghini, R. Can. J. Chem. 1988, 66, 1400-1404. (d) Hlavka, J.; Bitha, P.; Lin, Y.; Strohmeyer, T. J. Heterocycl. Chem. 1985, 22, 1317-1322. (e) Yoshida, J.; Yano, S.; Ozawa, T.; Kawabata, N. Tetrahedron Lett. 1984, 25, 2817-2820. (f) Kaye, P. T.; Meakins, G. D.; Smith, A. K.; Tirel, M. D. J. Chem. Soc., Perkin Trans. 1 1983, 1677-1680.
5. For examples of α-bromo 1,3-dicarbonyl compounds in organic transformations, see: (a) Misra, A. P.; Raj, K.; Bhaduri; A. P. Synth. Commun. 1999, 29, 3227-3236. (b) Coats, S. J.; Wasserman, H. H. Tetrahedron Lett. 1995, 36, 7735-7738. (c) Endo, M.; Droghini, R. Can. J. Chem. 1988, 66, 1400-1404. (d) Hlavka, J.; Bitha, P.; Lin, Y.; Strohmeyer, T. J. Heterocycl. Chem. 1985, 22, 1317-1322. (e) Yoshida, J.; Yano, S.; Ozawa, T.; Kawabata, N. Tetrahedron Lett. 1984, 25, 2817-2820. (f) Kaye, P. T.; Meakins, G. D.; Smith, A. K.; Tirel, M. D. J. Chem. Soc., Perkin Trans. 1 1983, 1677-1680.
6. For examples of α-bromo 1,3-dicarbonyl compounds in organic transformations, see: (a) Misra, A. P.; Raj, K.; Bhaduri; A. P. Synth. Commun. 1999, 29, 3227-3236. (b) Coats, S. J.; Wasserman, H. H. Tetrahedron Lett. 1995, 36, 7735-7738. (c) Endo, M.; Droghini, R. Can. J. Chem. 1988, 66, 1400-1404. (d) Hlavka, J.; Bitha, P.; Lin, Y.; Strohmeyer, T. J. Heterocycl. Chem. 1985, 22, 1317-1322. (e) Yoshida, J.; Yano, S.; Ozawa, T.; Kawabata, N. Tetrahedron Lett. 1984, 25, 2817-2820. (f) Kaye, P. T.; Meakins, G. D.; Smith, A. K.; Tirel, M. D. J. Chem. Soc., Perkin Trans. 1 1983, 1677-1680.
7. For examples of α-bromo 1,3-dicarbonyl compounds in organic transformations, see: (a) Misra, A. P.; Raj, K.; Bhaduri; A. P. Synth. Commun. 1999, 29, 3227-3236. (b) Coats, S. J.; Wasserman, H. H. Tetrahedron Lett. 1995, 36, 7735-7738. (c) Endo, M.; Droghini, R. Can. J. Chem. 1988, 66, 1400-1404. (d) Hlavka, J.; Bitha, P.; Lin, Y.; Strohmeyer, T. J. Heterocycl. Chem. 1985, 22, 1317-1322. (e) Yoshida, J.; Yano, S.; Ozawa, T.; Kawabata, N. Tetrahedron Lett. 1984, 25, 2817-2820. (f) Kaye, P. T.; Meakins, G. D.; Smith, A. K.; Tirel, M. D. J. Chem. Soc., Perkin Trans. 1 1983, 1677-1680.
8. (a) Bigelow, L. A.; Hanslick, R. S. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. 2, p 244.
9. (b) Hakam, K.; Thielmann, M.; Thielmann, T.; Winterfeldt, E. Tetrahedron 1987, 43, 2035-2044.
10. (c) Ogilvie, W.; Rank, W. Can. J. Chem. 1987, 65, 166-169.
11. (d) Dowd, P.; Kaufman, C.; Kaufman, P. J. Org. Chem. 1985, 50, 882-885.
12. 2/NaH: Boyd, R. E.; Rasmussen, C. R.; Press: J. B. Synth. Commun. 1995, 25, 1045-1051.
13. 3: Karimi, S.; Grohmann, K. G. J. Org. Chem. 1995, 60, 554-559.
14. (c) NBS/NaH: Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831.
15. (d) NBS/KH: Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140-3157.
16. (a) Coats, S. J.; Wasserman, H. H. Tetrahedron Lett. 1995, 36, 7735-7738.
17. (b) Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans. 1 1993, 3171-3175.
18. (c) Shi, X.; Dai, L. J. Org. Chem. 1993, 58, 4596-4598.
19. Yang, D.; Gu, S.; Yan, Y.-L.; Zhu, N.-Y.; Cheung, K.-K. J. Am. Chem. Soc. 2001, 123, 8612-8613.
20. For examples of Lewis acid-catalyzed transformations of β-keto esters, see: (a) Yang, D.; Ye, X.-Y.; Xu, M.; Pang, K.-W.; Cheung, K.-K. J. Am. Chem. Soc. 2000, 122, 1658-1663. (b) Yang, D.; Ye, X.-Y.; Gu, S.; Xu, M. J. Am. Chem. Soc. 1999, 121, 5579-5580. (c) Tateiwa, J.-I.; Hosomi, A. Eur. J. Org. Chem. 2001, 1445-1448. (d) Keller, E.; Feringa, B. L. Tetrahedron. Lett. 1996, 37, 1879-1882. (e) Colombo, M. I.; Signorella, S.; Mischne, M. P. Tetrahedron 1990, 46, 4149-4154. (f) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (g) Sasai, H.; Emori, E.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 5561-5564.
21. For examples of Lewis acid-catalyzed transformations of β-keto esters, see: (a) Yang, D.; Ye, X.-Y.; Xu, M.; Pang, K.-W.; Cheung, K.-K. J. Am. Chem. Soc. 2000, 122, 1658-1663. (b) Yang, D.; Ye, X.-Y.; Gu, S.; Xu, M. J. Am. Chem. Soc. 1999, 121, 5579-5580. (c) Tateiwa, J.-I.; Hosomi, A. Eur. J. Org. Chem. 2001, 1445-1448. (d) Keller, E.; Feringa, B. L. Tetrahedron. Lett. 1996, 37, 1879-1882. (e) Colombo, M. I.; Signorella, S.; Mischne, M. P. Tetrahedron 1990, 46, 4149-4154. (f) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (g) Sasai, H.; Emori, E.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 5561-5564.
22. For examples of Lewis acid-catalyzed transformations of β-keto esters, see: (a) Yang, D.; Ye, X.-Y.; Xu, M.; Pang, K.-W.; Cheung, K.-K. J. Am. Chem. Soc. 2000, 122, 1658-1663. (b) Yang, D.; Ye, X.-Y.; Gu, S.; Xu, M. J. Am. Chem. Soc. 1999, 121, 5579-5580. (c) Tateiwa, J.-I.; Hosomi, A. Eur. J. Org. Chem. 2001, 1445-1448. (d) Keller, E.; Feringa, B. L. Tetrahedron. Lett. 1996, 37, 1879-1882. (e) Colombo, M. I.; Signorella, S.; Mischne, M. P. Tetrahedron 1990, 46, 4149-4154. (f) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (g) Sasai, H.; Emori, E.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 5561-5564.
23. For examples of Lewis acid-catalyzed transformations of β-keto esters, see: (a) Yang, D.; Ye, X.-Y.; Xu, M.; Pang, K.-W.; Cheung, K.-K. J. Am. Chem. Soc. 2000, 122, 1658-1663. (b) Yang, D.; Ye, X.-Y.; Gu, S.; Xu, M. J. Am. Chem. Soc. 1999, 121, 5579-5580. (c) Tateiwa, J.-I.; Hosomi, A. Eur. J. Org. Chem. 2001, 1445-1448. (d) Keller, E.; Feringa, B. L. Tetrahedron. Lett. 1996, 37, 1879-1882. (e) Colombo, M. I.; Signorella, S.; Mischne, M. P. Tetrahedron 1990, 46, 4149-4154. (f) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (g) Sasai, H.; Emori, E.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 5561-5564.
24. For examples of Lewis acid-catalyzed transformations of β-keto esters, see: (a) Yang, D.; Ye, X.-Y.; Xu, M.; Pang, K.-W.; Cheung, K.-K. J. Am. Chem. Soc. 2000, 122, 1658-1663. (b) Yang, D.; Ye, X.-Y.; Gu, S.; Xu, M. J. Am. Chem. Soc. 1999, 121, 5579-5580. (c) Tateiwa, J.-I.; Hosomi, A. Eur. J. Org. Chem. 2001, 1445-1448. (d) Keller, E.; Feringa, B. L. Tetrahedron. Lett. 1996, 37, 1879-1882. (e) Colombo, M. I.; Signorella, S.; Mischne, M. P. Tetrahedron 1990, 46, 4149-4154. (f) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (g) Sasai, H.; Emori, E.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 5561-5564.
25. For examples of Lewis acid-catalyzed transformations of β-keto esters, see: (a) Yang, D.; Ye, X.-Y.; Xu, M.; Pang, K.-W.; Cheung, K.-K. J. Am. Chem. Soc. 2000, 122, 1658-1663. (b) Yang, D.; Ye, X.-Y.; Gu, S.; Xu, M. J. Am. Chem. Soc. 1999, 121, 5579-5580. (c) Tateiwa, J.-I.; Hosomi, A. Eur. J. Org. Chem. 2001, 1445-1448. (d) Keller, E.; Feringa, B. L. Tetrahedron. Lett. 1996, 37, 1879-1882. (e) Colombo, M. I.; Signorella, S.; Mischne, M. P. Tetrahedron 1990, 46, 4149-4154. (f) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (g) Sasai, H.; Emori, E.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 5561-5564.
26. For examples of Lewis acid-catalyzed transformations of β-keto esters, see: (a) Yang, D.; Ye, X.-Y.; Xu, M.; Pang, K.-W.; Cheung, K.-K. J. Am. Chem. Soc. 2000, 122, 1658-1663. (b) Yang, D.; Ye, X.-Y.; Gu, S.; Xu, M. J. Am. Chem. Soc. 1999, 121, 5579-5580. (c) Tateiwa, J.-I.; Hosomi, A. Eur. J. Org. Chem. 2001, 1445-1448. (d) Keller, E.; Feringa, B. L. Tetrahedron. Lett. 1996, 37, 1879-1882. (e) Colombo, M. I.; Signorella, S.; Mischne, M. P. Tetrahedron 1990, 46, 4149-4154. (f) Sasai, H.; Arai, T.; Satow, Y.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194-6198. (g) Sasai, H.; Emori, E.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1996, 37, 5561-5564.
27. (a) Hintermann, L.; Togni, A. Helv. Chim. Acta 2000, 83, 2425-2435.
28. (b) Hintermann, L.; Togni, A. Angew. Chem., Int. Ed. 2000, 39, 4359-4362.
29. (c) Piana, S.; Devillers, I.; Togni, A.; Rothlisberger, U. Angew. Chem., Int. Ed. 2002, 41, 979-982.
30. Chlorination with NCS: (a) Davies, D. T.; Kapur, N.; Parsons, A. F. Tetrahedron 2000, 56, 3941-3949. (b) Tanaka, K.; Chen, X.; Yoneda, F. Tetrahedron 1988, 44, 3241-3249.
31. Chlorination with NCS: (a) Davies, D. T.; Kapur, N.; Parsons, A. F. Tetrahedron 2000, 56, 3941-3949. (b) Tanaka, K.; Chen, X.; Yoneda, F. Tetrahedron 1988, 44, 3241-3249.
32. Iodination with NIS: (a) Cossy, J.; Thellend, A. Tetrahedron Lett. 1990, 31, 1427-1428. (b) Curran, D. P.; Morgan, T. M.; Schwartz, C. E.; Snider, B. B.; Dombroski, M. A. J. Am. Chem. Soc. 1991, 113, 6607-6617.
33. Iodination with NIS: (a) Cossy, J.; Thellend, A. Tetrahedron Lett. 1990, 31, 1427-1428. (b) Curran, D. P.; Morgan, T. M.; Schwartz, C. E.; Snider, B. B.; Dombroski, M. A. J. Am. Chem. Soc. 1991, 113, 6607-6617.
34. For examples of α-chloro 1,3-dicarbonyl compounds in organic transformations, see: (a) Hayashi, Y.; Orikasa, S.; Tanaka, K.; Kanoh, K.; Kiso, Y. J. Org. Chem. 2000, 65, 8402-8405. (b) Guerin, D.; Carlier, R.; Lorcy, D. J. Org. Chem. 2000, 65, 6069-6072. (c) Vasudevan, A.; Mavandadi, F.; Chen, L.; Gangjee, A. J. Org. Chem. 1999, 64, 634-638. (d) Hayes, T.; Villani, R.; Weinreb, S. M. J. Am. Chem. Soc. 1988, 110, 5533-5543. (e) Blount, J. F.; Coffen, D. L.; Katonak, D. A. J. Org. Chem. 1978, 43, 3821-3824.
35. For examples of α-chloro 1,3-dicarbonyl compounds in organic transformations, see: (a) Hayashi, Y.; Orikasa, S.; Tanaka, K.; Kanoh, K.; Kiso, Y. J. Org. Chem. 2000, 65, 8402-8405. (b) Guerin, D.; Carlier, R.; Lorcy, D. J. Org. Chem. 2000, 65, 6069-6072. (c) Vasudevan, A.; Mavandadi, F.; Chen, L.; Gangjee, A. J. Org. Chem. 1999, 64, 634-638. (d) Hayes, T.; Villani, R.; Weinreb, S. M. J. Am. Chem. Soc. 1988, 110, 5533-5543. (e) Blount, J. F.; Coffen, D. L.; Katonak, D. A. J. Org. Chem. 1978, 43, 3821-3824.
36. For examples of α-chloro 1,3-dicarbonyl compounds in organic transformations, see: (a) Hayashi, Y.; Orikasa, S.; Tanaka, K.; Kanoh, K.; Kiso, Y. J. Org. Chem. 2000, 65, 8402-8405. (b) Guerin, D.; Carlier, R.; Lorcy, D. J. Org. Chem. 2000, 65, 6069-6072. (c) Vasudevan, A.; Mavandadi, F.; Chen, L.; Gangjee, A. J. Org. Chem. 1999, 64, 634-638. (d) Hayes, T.; Villani, R.; Weinreb, S. M. J. Am. Chem. Soc. 1988, 110, 5533-5543. (e) Blount, J. F.; Coffen, D. L.; Katonak, D. A. J. Org. Chem. 1978, 43, 3821-3824.
37. For examples of α-chloro 1,3-dicarbonyl compounds in organic transformations, see: (a) Hayashi, Y.; Orikasa, S.; Tanaka, K.; Kanoh, K.; Kiso, Y. J. Org. Chem. 2000, 65, 8402-8405. (b) Guerin, D.; Carlier, R.; Lorcy, D. J. Org. Chem. 2000, 65, 6069-6072. (c) Vasudevan, A.; Mavandadi, F.; Chen, L.; Gangjee, A. J. Org. Chem. 1999, 64, 634-638. (d) Hayes, T.; Villani, R.; Weinreb, S. M. J. Am. Chem. Soc. 1988, 110, 5533-5543. (e) Blount, J. F.; Coffen, D. L.; Katonak, D. A. J. Org. Chem. 1978, 43, 3821-3824.
38. For examples of α-chloro 1,3-dicarbonyl compounds in organic transformations, see: (a) Hayashi, Y.; Orikasa, S.; Tanaka, K.; Kanoh, K.; Kiso, Y. J. Org. Chem. 2000, 65, 8402-8405. (b) Guerin, D.; Carlier, R.; Lorcy, D. J. Org. Chem. 2000, 65, 6069-6072. (c) Vasudevan, A.; Mavandadi, F.; Chen, L.; Gangjee, A. J. Org. Chem. 1999, 64, 634-638. (d) Hayes, T.; Villani, R.; Weinreb, S. M. J. Am. Chem. Soc. 1988, 110, 5533-5543. (e) Blount, J. F.; Coffen, D. L.; Katonak, D. A. J. Org. Chem. 1978, 43, 3821-3824.
39. For examples of α-iodo 1,3-dicarbonyl compounds in organic transformations, see: (a) Kang, J.; Lee, J. H.; Noh, S. B.; Oh, C. S.; Kim, H. Y.; Chung, B. Y. Synlett 1990, 153-154. (b) Curran, D. P.; Chen, M. S.; Spletzer, E.; Seong, C. M.; Chang, C. T. J. Am. Chem. Soc. 1989, 111, 8872-8878. (c) Reference 4c.
40. For examples of α-iodo 1,3-dicarbonyl compounds in organic transformations, see: (a) Kang, J.; Lee, J. H.; Noh, S. B.; Oh, C. S.; Kim, H. Y.; Chung, B. Y. Synlett 1990, 153-154. (b) Curran, D. P.; Chen, M. S.; Spletzer, E.; Seong, C. M.; Chang, C. T. J. Am. Chem. Soc. 1989, 111, 8872-8878. (c) Reference 4c.
41. For examples of α-iodo 1,3-dicarbonyl compounds in organic transformations, see: (a) Kang, J.; Lee, J. H.; Noh, S. B.; Oh, C. S.; Kim, H. Y.; Chung, B. Y. Synlett 1990, 153-154. (b) Curran, D. P.; Chen, M. S.; Spletzer, E.; Seong, C. M.; Chang, C. T. J. Am. Chem. Soc. 1989, 111, 8872-8878. (c) Reference 4c.
42. Hoffman, R. V.; Weiner, W. S.; Maslouh, N. J. Org. Chem. 2001, 66, 5790-5795.
43. Honda, Y.; Katayama, S.; Kojima, M.; Suzuki, T.; Izawa, K. Org. Lett. 2002, 4, 447-449.
44. For more examples of asymmetric α-halogenation, see: (a) Wack, H.; Taggi, A. E.; Hafez, A. M.; Drury, W. J.; Lectka, T. J. Am. Chem. Soc. 2001, 123, 1531-1532. (b) Hafez, A. M.; Taggi, A. E.; Wack, H.; Esterbrook, J.; Lectka, T. Org. Lett. 2001, 3, 2049-2051. (c) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729.
45. For more examples of asymmetric α-halogenation, see: (a) Wack, H.; Taggi, A. E.; Hafez, A. M.; Drury, W. J.; Lectka, T. J. Am. Chem. Soc. 2001, 123, 1531-1532. (b) Hafez, A. M.; Taggi, A. E.; Wack, H.; Esterbrook, J.; Lectka, T. Org. Lett. 2001, 3, 2049-2051. (c) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729.
46. For more examples of asymmetric α-halogenation, see: (a) Wack, H.; Taggi, A. E.; Hafez, A. M.; Drury, W. J.; Lectka, T. J. Am. Chem. Soc. 2001, 123, 1531-1532. (b) Hafez, A. M.; Taggi, A. E.; Wack, H.; Esterbrook, J.; Lectka, T. Org. Lett. 2001, 3, 2049-2051. (c) Shibata, N.; Suzuki, E.; Takeuchi, Y. J. Am. Chem. Soc. 2000, 122, 10728-10729.
47. (a) Stotter, P. L.; Hill, K. A. Tetrahedron Lett. 1972, 4067-4070.
48. (b) Sum, P.-E.; Weiler, L. Can. J. Chem. 1979, 57, 1475-1480.