Palladium-Catalyzed Amidation of Enol Triflates: A New Synthesis of Enamides

Organic Letters

Volumn 5, Issue 24, 2003, Pages 4749-4752

  Wallace, Debra J ^a   Klauber, David J ^a   Chen, Cheng Yi ^a   Volante, Ralph P ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; CARBAMIC ACID DERIVATIVE; PALLADIUM; SULFONAMIDE; TRIFLUOROMETHANESULFONIC ACID;

AMIDATION; ARTICLE; CATALYSIS; SYNTHESIS;

EID: 0347411032     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035959g     Document Type: Article

References (28)

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19. For stereocontrolled synthesis of 1,2-disubstituted enamides, see: (a) Furstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955. (b) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407 and references therein. For stereoselective preparation of trisubstituted enamides, see: Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67 and references therein.
20. For stereocontrolled synthesis of 1,2-disubstituted enamides, see: (a) Furstner, A.; Brehm, C.; Cancho-Grande, Y. Org. Lett. 2001, 3, 3955. (b) Snider, B. B.; Song, F. Org. Lett. 2000, 2, 407 and references therein. For stereoselective preparation of trisubstituted enamides, see: Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67 and references therein.
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22. For copper-catalyzed amidations of vinyl halides, see: (a) Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L Org. Lett. 2003, 5, 3667. (b) Shen, R.; Porco, J. A. Jr. Org. Lett. 2000, 2, 1333. (c) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443. For a palladium-catalyzed intramolecular reaction, see: Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111.
23. For copper-catalyzed amidations of vinyl halides, see: (a) Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L Org. Lett. 2003, 5, 3667. (b) Shen, R.; Porco, J. A. Jr. Org. Lett. 2000, 2, 1333. (c) Ogawa, T.; Kiji, T.; Hayami, K.; Suzuki, H. Chem. Lett. 1991, 1443. For a palladium-catalyzed intramolecular reaction, see: Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111.
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26. 13C, IR, and HRMS and/or elemental analysis.
27. +) theory 258.1858, measured 258.1851.
28. While a conjugate addition/elimination pathway could operate for this enol triflate, we feel that this is unlikely due to the lack of reactivity in the absence of palladium (<5% conversion after 24 h). We thank a referee for alerting us to this possibility.