Heck Reactions Starting from Silyl Enol Ethers - A Simple One-Pot Nonaflation-Coupling Procedure for the Synthesis of 1,3-Dienes

Synlett

Volumn 1997, Issue 10, 1997, Pages 1141-1142

  Webel, Matthias ^a   Reissig, Hans Ulrich ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002713206     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-976     Document Type: Article

References (21)

1. Hirsch, E.; Hünig, S.; Reissig, H.-U. Chem. Ber. 1982, 115, 3687. For a very similar O-acylation of enolates employing acyl fluorides, see: Limat, D.; Schlosser, M. Tetrahedron 1995, 51, 5799.
2. Hirsch, E.; Hünig, S.; Reissig, H.-U. Chem. Ber. 1982, 115, 3687. For a very similar O-acylation of enolates employing acyl fluorides, see: Limat, D.; Schlosser, M. Tetrahedron 1995, 51, 5799.
3. For alternative syntheses of alkenylnonaflates and the more commonly used alkenyltriflates as well as their reactions, see: Stang, P.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85. - Ritter, K. Synthesis 1993, 735. - For the use of perfluoroalkanesulfonyl fluorides, see: Subramanian, L. R.; Bentz, H.; Hanack, M. Synthesis 1973, 293. - Zhu, Z.; Tian, W.; Liao, Q. Tetrahedron Lett. 1996, 37, 8553.
4. For alternative syntheses of alkenylnonaflates and the more commonly used alkenyltriflates as well as their reactions, see: Stang, P.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85. - Ritter, K. Synthesis 1993, 735. - For the use of perfluoroalkanesulfonyl fluorides, see: Subramanian, L. R.; Bentz, H.; Hanack, M. Synthesis 1973, 293. - Zhu, Z.; Tian, W.; Liao, Q. Tetrahedron Lett. 1996, 37, 8553.
5. For alternative syntheses of alkenylnonaflates and the more commonly used alkenyltriflates as well as their reactions, see: Stang, P.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85. - Ritter, K. Synthesis 1993, 735. - For the use of perfluoroalkanesulfonyl fluorides, see: Subramanian, L. R.; Bentz, H.; Hanack, M. Synthesis 1973, 293. - Zhu, Z.; Tian, W.; Liao, Q. Tetrahedron Lett. 1996, 37, 8553.
6. For alternative syntheses of alkenylnonaflates and the more commonly used alkenyltriflates as well as their reactions, see: Stang, P.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85. - Ritter, K. Synthesis 1993, 735. - For the use of perfluoroalkanesulfonyl fluorides, see: Subramanian, L. R.; Bentz, H.; Hanack, M. Synthesis 1973, 293. - Zhu, Z.; Tian, W.; Liao, Q. Tetrahedron Lett. 1996, 37, 8553.
7. Khan, F. A.; Czerwonka, R.; Reissig, H.-U. Synlett 1996, 533.
8. Reviews: 4a) Heck, R. F. in Palladium Reagents in Organic Synthesis, Academic Press, Orlando FL, 1985.
9. 4b) Heck, R. F. in Comprehensive Organic Synthesis (Eds.: Trost, B. M.; Fleming, I.), Vol. 4, p. 833, Pergamon Press, Oxford, 1991.
10. 4c) de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
11. 4c) de Meijere, A.; Meyer, F. E. Angew. Chem. 1994, 106, 2473; Angew. Chem. Int. Ed. Engl. 1994, 33, 2379.
12. 4d) Tsuji, J. in Palladium Reagents and Catalysts, J. Wiley & Sons, Chichester, 1995.
13. TBAF was purchased from ABCR as 1 M solution in THF. It was dried with freshly activated pulverized molecular sieves (4 X). See: Seebach, D.; Beck, A. K.; Mukhopadhyay, T.; Thomas E. Helv. Chim. Acta 1982, 65, 1102.
14. For Heck reactions of alkenyltriflates, see: Scott, W. J.; Peña, M. R.; Swärd, K.; Stoessel, S. J.; Stille, J. K. J. Org. Chem. 1985, 50, 2302. - We employed conditions as described by Burini, A.; Cacchi, S.; Pace, P.; Pietroni, B. R. Synlett 1995, 677.
15. For Heck reactions of alkenyltriflates, see: Scott, W. J.; Peña, M. R.; Swärd, K.; Stoessel, S. J.; Stille, J. K. J. Org. Chem. 1985, 50, 2302. - We employed conditions as described by Burini, A.; Cacchi, S.; Pace, P.; Pietroni, B. R. Synlett 1995, 677.
16. 2, hexane/ethyl acetate, 10:1) thus furnishing 0.63 g (64%) of pure 8 as colorless liquid (Tamura, R.; Kato, M.; Saegusa, K.; Kakihana, M.; Oda, D. J. Org. Chem. 1987, 52, 4121).
17. The lower yield may be due to the steric hindrance in the coupling step. We are not aware of a similar example bearing a terty-butyl group.
18. For recent alternatives, see: Comins, D. L.; Benjelloun, N. R. Tetrahedron Lett. 1994, 35, 829.
19. There are only singular examples of the use of aryl- and alkenylnonaflates in Pd-catalyzed coupling reactions, see ref. 4c and Bräse, S.; de Meijere, A. Angew. Chem. 1995, 107, 2741; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545.
20. There are only singular examples of the use of aryl- and alkenylnonaflates in Pd-catalyzed coupling reactions, see ref. 4c and Bräse, S.; de Meijere, A. Angew. Chem. 1995, 107, 2741; Angew. Chem. Int. Ed. Engl. 1995, 34, 2545.
21. Review: Chan, T.-H. in Comprehensive Organic Synthesis (Eds.: Trost, B. M.; Fleming, I.), Vol. 2, p. 595, Pergamon Press, Oxford, 1991.