DMF as a dimethylamine equivalent in the palladium-catalyzed nucleophilic substitution of naphthylmethyl and allyl acetates

Tetrahedron Letters

Volumn 38, Issue 1, 1997, Pages 77-80

  Toffano, Martial ^a   Legros, Jean Yves ^a   Fiaud, Jean Claude ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHALENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0031014736     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02219-8     Document Type: Article

References (19)

1. a) Legros, J.Y.; Fiaud, J.C. Tetrahedron Lett. 1992, 33, 2509-2510.
2. b) Legros, J.Y.; Toffano, M.; Fiaud, J.C. Tetrahedron 1995, 51, 3235-3246.
3. c) Legros, J.Y.; Toffano, M.; Fiaud, J.C. Tetrahedron: Asymmetry 1995, 6, 1899-1902.
4. For recent reports, see: a) Godleski, S.A. in "Comprehensive Organic Synthesis", Trost, B.M.; Fleming, I.; Semmelhack, M.F. Eds., Pergamon Press: Oxford, 1991, 4, 585-661.
5. b) Tsuji, J. "Palladium Reagents and Catalysts. Innovations in Organic Synthesis", John Wiley & Sons: Chichester, 1995, 290-422.
6. c) Trost, B.M.; Van Vranken, D.L. Chem. Rev. 1996, 96, 395-422.
7. Although DMF is a common formylating agent, the dimethylamine liberated by this process is to our knowledge rarely used: see Comins, D.L.; Joseph, S.P. in "Encyclopedia of Reagents for Organic Synthesis", Paquette, L.A. Ed., John Wiley & Sons: Chichester, 1995, 3, 2072-2075.
8. For some recent examples: a) Kuo, D.L. Heterocycles 1993, 36, 1463-1469.
9. b) Uozumi, Y.; Tanahashi, A.; Hayashi, T. J. Org. Chem. 1993, 58, 6826-6832.
10. c) Yamazaki, A.; Achiwa, K. Tetrahedron: Asymmetry 1995, 6, 1021-1024.
11. d) Thorey, C.; Wilken, J.; Hénin, F.; Martens, J.; Mehler, T.; Muzart J. Tetrahedron Lett. 1995, 36, 5527-5530.
12. e) Yamazaki, A.; Achiwa, I.; Achiwa, K. Tetrahedron: Asymmetry 1996, 7, 403-406.
13. f) Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031-1037.
14. g) Jin, Z.; Fuchs, P.L. Tetrahedron Lett 1996, 37, 5253-5256.
15. a) Bäckvall, J.E.; Nordberg, R.E.; Nyström, J.E.; Högberg, T.; Ulff, B. J.Org.Chem. 1981, 46, 3479-3483.
16. b) Genêt, J.P.; Balabane, M.; Bäckvall, J.E.; Nyström, J.E. Tetrahedron Lett. 1983, 24, 2745-2748.
17. c) Nikaido, M.; Aslanian, R.; Scavo, F.; Helquist, P.; Akermark, B.; Bäckvall, J.E. J.Org.Chem., 1984, 49, 4738-4740.
18. d) Bäckvall, J.E.; Juntunsen, S.K. J. Am. Chem. Soc. 1987, 109, 6396-6403.
19. e) Genêt, J.P.; Thorimbert, S.; Mallart, S.; Kardos, N. Synthesis 1993, 321-324.