Palladium catalysed enamine synthesis from vinyl triflates

Tetrahedron Letters

Volumn 43, Issue 50, 2002, Pages 9085-9088

  Willis, Michael C ^a   Brace, Gareth N ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; CARBONIC ACID DERIVATIVE; CHEMICAL COMPOUND; ENAMINE; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID; VINYL DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; SYNTHESIS;

EID: 0037049225     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02249-9     Document Type: Article

References (21)

1. For general reviews on enamine chemistry, see: (a) Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Oxford: Pergamon, 1991; (b) Cook, A. G., Ed., Enamines; New York: Marcel Decker, 1988.
2. For general reviews on enamine chemistry, see: (a) Whitesell, J. K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Oxford: Pergamon, 1991; (b) Cook, A. G., Ed., Enamines; New York: Marcel Decker, 1988.
3. For example: (a) Aznar, F.; Valdés, C.; Cabal, M.-P. Tetrahedron Lett. 2000, 41, 5683; (b) Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7111.
4. For example: (a) Aznar, F.; Valdés, C.; Cabal, M.-P. Tetrahedron Lett. 2000, 41, 5683; (b) Hird, N. W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7111.
5. For an example, see: Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
6. White W.A., Weingarten H. J. Org. Chem. 32:1967;213.
7. Martin S.F., Gompper R. J. Org. Chem. 39:1974;2814.
8. For a review on the uses and preparations of triflate derivatives, see: Ritter, K. Synthesis 1993, 735.
9. For reviews, see: (a) Hartwig, J. F. In Modern Amination Methods; Ricci, A. Ed.; Weinheim: Wiley-VCH, 2000; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805; (c) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
10. For reviews, see: (a) Hartwig, J. F. In Modern Amination Methods; Ricci, A. Ed.; Weinheim: Wiley-VCH, 2000; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805; (c) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
11. For reviews, see: (a) Hartwig, J. F. In Modern Amination Methods; Ricci, A. Ed.; Weinheim: Wiley-VCH, 2000; (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805; (c) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
12. During the course of this study an example of an intramolecular palladium catalysed coupling between a vinyl bromide and an amide was reported; Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111; an example of the intermolecular palladium catalysed coupling of vinyl bromides and azoles has also recently appeared: Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623.
13. During the course of this study an example of an intramolecular palladium catalysed coupling between a vinyl bromide and an amide was reported; Kozawa, Y.; Mori, M. Tetrahedron Lett. 2002, 43, 111; an example of the intermolecular palladium catalysed coupling of vinyl bromides and azoles has also recently appeared: Lebedev, A. Y.; Izmer, V. V.; Kazyul'kin, D. N.; Beletskaya, I. P.; Voskoboynikov, A. Z. Org. Lett. 2002, 4, 623.
14. Wolfe J.P., Tomori H., Sadighi J.P., Yin J., Buchwald S.L. J. Org. Chem. 65:2000;1158.
15. Yin J.J., Buchwald S.L. J. Am. Chem. Soc. 124:2002;6043.
16. Hamann B.C., Hartwig J.F. J. Am. Chem. Soc. 120:1998;7369.
17. Yang B.H., Buchwald S.L. Org. Lett. 1:1999;35.
18. Starting triflate recovered in 93% yield.
19. 1H NMR spectroscopy for determination of the percentage conversion to product, or taken immediately into the next reaction.
20. 3, 300 MHz) 1.62-1.79 (2H, m), 1.85-2.08 (2H, m), 2.41-2.55 (2H, m), 2.56-2.68 (2H, m), 2.69-2.86 (2H, m), 3.73 (4H, t, J 3.9 Hz) 3.75-3.83 (1H, m), 7.00-7.09 (1H, m), 7.09-7.21 (2H, m), 7.70 (1H, d, J 6.6 Hz).
21. For a recent example of the indirect conversion of a vinyl triflate to the corresponding ketone, see; Hynes, J., Jr.; Nasser, T.; Overman, L. E.; Watson, D. A. Org. Lett. 2002, 4, 929.