Copper-catalyzed coupling of amides and carbamates with vinyl halides

Organic Letters

Volumn 5, Issue 20, 2003, Pages 3667-3669

  Jiang, Lei ^a   Job, Gabriel E ^a   Klapars, Artis ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINO ACID; BROMIDE; CARBAMIC ACID DERIVATIVE; COPPER; ESTER; ETHYLENEDIAMINE DERIVATIVE; HALIDE; IODIDE; IODINATED HYDROCARBON; SILANE DERIVATIVE; VINYL BROMIDE; VINYL DERIVATIVE;

AMIDATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

AMIDES; CARBAMATES; CATALYSIS; COPPER; HYDROCARBONS, IODINATED; VINYL COMPOUNDS;

EID: 0142106421     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035355c     Document Type: Article

References (34)

1. (a) Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations; Wiley-VCH: New York, 1999.
2. (b) Fürstner, A.; Dierkes, T.; Thiel, O. R.; Blanda, G. Chem Eur. J. 2001, 7, 5286.
3. (a) Galinis, D. L.; McKee, T. C.; Pannell, L. K.; Cardellina, J. H., II; Boyd, M. R. J. Org. Chem. 1997, 62, 8968.
4. (b) McKee, T. C.; Galinis, D. L.; Pannell, L. K.; Cardellina, J. H., II; Laasko, J.; Ireland, C. M.; Murray, L.; Capon, R. J.; Boyd, M. R. J. Org. Chem. 1998, 63, 7805.
5. (c) Suzumura, K.-i.; Takahashi, I.; Matsumoto, H.; Nagai, K.; Setiawan, B.; Rantiamodjo, R. M.; Suzuki, K.-i.; Nagano, N. Tetrahedron Lett. 1997, 38, 7573.
6. (d) Kim, J. W.; Shin-ya, K.; Furihata, K.; Hayakawa, Y. Seto, H. J. Org. Chem. 1999, 64, 153.
7. (e) Erickson, K. L.; Beutler, J.; Cardellina, J. H., II; Boyd, M. R. J. Org. Chem. 1997, 62, 8188.
8. (f) Dekker, K. A.; Aiello, R. J.; Hirai, H.; Inagaki, T.; Sakakibara, T. ; Suzuki, Y.; Thompson, J. F.; Yamauchi, Y.; Kojima, N. J. Antibiot. 1998, 51, 14.
9. (g) Kunze, B.; Jansen, R.; Sasse, F.; Hofle, G.; Reichenbach, H. J. Antibiot. 1998, 51, 1075.
10. (a) Mohre, H.; Kilian, R. Tetrahedron 1969, 25, 5745.
11. (b) Kondo, T.; Tanaka, A.; Kotachi, S.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1995, 413.
12. (a) Boeckmann, R. K., Jr.; Goldstein, S. W.; Walters, M. A. J. Am. Chem. Soc. 1988, 110, 8250
13. (a) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407.
14. (b) Brettle, R.; Mosedale, A. J. J. Chem. Soc., Perkin Trans. 1 1988, 2, 185.
15. For palladium-catalyzed C-N bond formation, see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. For leading references on the copper-catalyzed C-N bond formation, see: (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (e) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453. (f) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
16. For palladium-catalyzed C-N bond formation, see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. For leading references on the copper-catalyzed C-N bond formation, see: (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (e) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453. (f) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
17. For palladium-catalyzed C-N bond formation, see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. For leading references on the copper-catalyzed C-N bond formation, see: (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (e) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453. (f) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
18. For palladium-catalyzed C-N bond formation, see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. For leading references on the copper-catalyzed C-N bond formation, see: (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (e) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453. (f) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
19. For palladium-catalyzed C-N bond formation, see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. For leading references on the copper-catalyzed C-N bond formation, see: (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (e) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453. (f) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
20. For palladium-catalyzed C-N bond formation, see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. For leading references on the copper-catalyzed C-N bond formation, see: (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (e) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453. (f) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
21. For palladium-catalyzed C-N bond formation, see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. For leading references on the copper-catalyzed C-N bond formation, see: (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (e) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453. (f) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
22. For palladium-catalyzed C-N bond formation, see: (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1051. (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131. For leading references on the copper-catalyzed C-N bond formation, see: (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793. (c) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727. (d) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315. (e) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453. (f) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
23. (a) Palomo, C.; Aizpurua, J. M.; Legido, M.; Picard, J. P.; Dunogues, J. ; Constantieux, T. Tetrahedron Lett. 1992, 33, 3903.
24. (b) Cuevas, J.-c.; Patil, P.; Snieckus, V. Tetrahedron Lett. 1989, 30, 5841.
25. (a) Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111.
26. For palladium-catalyzed vinylation of azoles, see: (b) Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623
27. For palladium-catalyzed vinylation of amines, see: (c) Barluenga, J.; Fernández, M. A.; Aznar, F.; Valdés, C. Chem. Commun. 2002, 2362.
28. (d) Willis, M. C.; Brace, G. N. Tetrahedron Lett. 2002, 43, 9085.
29. (a) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443.
30. (b) Shen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333.
31. (c) Shen, R.; Lin, C. T.; Porco, J. A., Jr. J. Am. Chem. Soc. 2002, 124, 5650.
32. While this manuscript was being prepared, a paper utilizing a stoichiometric quantity of CuTc and N,N′-dimethylethylenediamine was reported: Wang, X.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 6040.
33. Shakespeare, W. C. Tetrahedron Lett. 1999, 40, 2035.
34. For a recent report on asymmetric hydrogenation of β-acylamido acrylates, see: Holz, J.; Monsees, A.; Jiao, H.; You, J.; Kormarov, I. V.; Fischer, C.; Drauz, K.; Borner, A. J. Org. Chem. 2003, 68, 1701.