Palladium-catalysed coupling reactions: (Z)-vinyl (N-N-diisopropyl) carbamate group as an efficient precursor of a (Z)-vinyl triflate function

Synthesis

Volumn , Issue 18, 2004, Pages 3017-3022

  Porée, François Hugues ^a   Barbion, Julien ^a   Dhulut, Sylvie ^a   Betzer, Jean François ^a   Pancrazi, Ange ^a   Ardisson, Janick ^a  

^a 5 Mail Gay Lussac   (France)

Author keywords

Alkenes; Allylations; Coupling; Palladium; Tin

Indexed keywords

CATALYSIS; CHEMICAL BONDS; DERIVATIVES; PHASE TRANSITIONS; REACTION KINETICS; VINYL RESINS;

COUPLING REACTIONS; DOUBLE BONDS;

PALLADIUM;

3 [(TERT BUTYLDIMETHYLSILYL)OXY] 2,4 DIMETHYL 6 (DIPHENOXYPHOSPHINYL)HEX 5 ENE; 3 [(TERT BUTYLDIMETHYLSILYL)OXY] 2,4 DIMETHYL 6 [(TRIFLUOROMETHYLSULFONYL)OXY]HEX 5 ENE; 3 [(TERT BUTYLDIMETHYLSILYL)OXY] 2,4 DIMETHYL 6 PHENYLHEX 5 ENE; 3 [(TERT BUTYLDIMETHYLSILYL)OXY] 2,4 DIMETHYL 8 PHENYLOCT 5 EN 7 YNE; 3 [(TERT BUTYLDIMETHYLSILYL)OXY] 2,4 DIMETHYLOCTA 5,7 DIENE; 3 [{TERT BUTYLDIMETHYLSILYL)OXY] 2,4 DIMETHYL 6 PHENYLHEX 5 ENE; CARBAMIC ACID DERIVATIVE; PALLADIUM; TRIFLUOROMETHANESULFONIC ACID VINYL ESTER; UNCLASSIFIED DRUG; VINYL (N,N DIISOPROPYL)CARBAMATE; VINYL DERIVATIVE; VINYL PHOSPHATE;

ALLYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; GEOMETRY;

EID: 11144279278     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834878     Document Type: Article

References (50)

1. (a) Hoppe, D. Angew. Chem., Int. Ed. Engl. 1984, 23, 932.
2. (b) Hoppe, D.; Zschage, O. Angew. Chem., Int. Ed. Engl. 1989, 28, 69.
3. (c) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 8389.
4. (d) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282.
5. (a) Paulsen, H.; Hoppe, D. Tetrahedron 1992, 48, 5667.
6. (b) Férézou, J.-P.; Julia, M.; Li, Y.; Liu, L. W.; Pancrazi, A. Bull. Soc. Chim. Fr. 1995, 132, 428.
7. (c) Smith, N. D.; Kocienski, P. J.; Street, S. D. A. Synthesis 1996, 652.
8. (d) Berque, I.; Le Ménez, P.; Razon, P.; Aniès, C.; Pancrazi, A.; Ardisson, J.; Neuman, A.; Prangé, T.; Brion, J.-D. Synlett 1988, 1132.
9. (e) Berque, I.; Le Ménez, P.; Razon, P.; Pancrazi, A.; Ardisson, J.; Brion, J.-D. Synlett 1988, 1135.
10. (f) Berque, I.; Le Ménez, P.; Razon, P.; Mahuteau, J.; Férézou, J. P.; Pancrazi, A.; Ardisson, J. J. Org. Chem. 1999, 64, 373.
11. Hoppe, D.; Hanko, R.; Brönneke, A.; Lichtenberg, F.; van Hülsen, E. Chem. Ber. 1985, 118, 2822.
12. Taylor, R. E.; Risatti, C. A.; Engelhardt, C.; Schmitt, M. J. Org. Lett. 2003, 5, 1377.
13. (a) Wadman, S.; Whitby, R.; Yeates, C.; Kocienski, P.; Cooper, K. J. Chem. Soc., Chem. Commun. 1987, 241.
14. (b) Kocienski, P.; Dixon, N. J. Synlett 1989, 52.
15. (c) For transformation of (Z)- or (E)-vinyl carbamate into the corresponding (E)-vinyl iodide derivative see: Liard, A.; Marek, I. J. Org. Chem. 2000, 65, 7218.
16. (d) Madec, D.; Pujol, S.; Henryon, V.; Férézou, J.-P. Synlett 1995, 435.
17. (a) Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246.
18. (b) Wenkert, E.; Michelotti, E. L.; Swindell, C. S.; Tingoli, M. J. Org. Chem. 1984, 49, 4894.
19. Porée, F.-H.; Clavel, A.; Betzer, J.-F.; Pancrazi, A.; Ardisson, J. Tetrahedron Lett. 2003, 44, 7553.
20. (a) Hayashi, T.; Katsuro, Y.; Okamoto, Y.; Kumada, M. Tetrahedron Lett. 1981, 22, 4449.
21. (b) Sengupta, S.; Leite, M.; Raslan, D. S.; Quesnelle, C.; Snieckus, V. J. Org. Chem. 1992, 57, 4066.
22. (c) Hayashi, T.; Katsuro, Y.; Kumada, M. Tetrahedron Lett. 1980, 21, 3915.
23. (d) Grouse, G. D.; Paquette, L. A. J. Org. Chem. 1981, 46, 4272.
24. Madec, D.; Henryon, V.; Férézou, J.-P. Tetrahedron Lett. 1999, 40, 8103.
25. Henryon, V.; Liu, L. W.; Lopez, R.; Prunet, J.; Férézou, J.-P. Synthesis 2001, 2401.
26. Jackson, J. A.; Hammond, G. B.; Wiemer, D. F. J. Org. Chem. 1989, 54, 4750.
27. For Ni-catalysed coupling reactions of vinyl phosphates with alkyl- or trimethylsilylmethyl Grignard reagents see: (a) Weiler, L.; Sum, F.-W. Can. J. Chem. 1979, 57, 1431.
28. (b) Lee, K.; Wiemer, D. F. Tetrahedron Lett. 1993, 34, 2433.
29. (c) Iwashima, M.; Nagaoka, H.; Kobayashi, K.; Yamada, Y. Tetrahedron Lett. 1992, 33, 81.
30. For a recent Pd-catalysed coupling reaction, see: Miller, J. A. Tetrahedron Lett. 2002, 43, 7111.
31. For Pd-catalysed coupling reactions of α-hetero substituted vinyl phosphates, see: (a) Nicolaou, K. C.; Shi, G.-Q.; Gunzner, J. L.; Gärtner, P.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 5467.
32. (b) Lepifre, F.; Buon, C.; Rabot, R.; Bouyssou, P.; Coudert, G. Tetrahedron Lett. 1999, 40, 6373.
33. (c) Sasaki, M.; Honda, S.; Noguchi, T.; Takakura, H.; Tachibana, K. Synlett 2000, 838.
34. (a) Ritter, K. Synthesis 1993, 735.
35. (b) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
36. (c) Tsushima, K.; Araki, K.; Murai, A. Chem. Lett. 1989, 1313.
37. (a) Gibbs, R. A.; Krishnam, U.; Dolence, J. M.; Poulter, C. D. J. Org. Chem. 1995, 60, 7821.
38. (b) Mu, Y. Q.; Gibbs, R. A. Tetrahedron Lett. 1995, 36, 5669.
39. (c) Gibbs, R. A.; Krishnan, U. Tetrahedron Lett. 1994, 35, 2509.
40. (a) Sato, Y.; Watanabe, S.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2589.
41. (b) Kondo, K.; Sodeoka, M.; Mori, M.; Shibasaki, M. Synthesis 1993, 920.
42. (c) Niwa, H.; Watanabe, M.; Inagaki, H.; Yamada, K. Tetrahedron 1994, 50, 7385.
43. (d) Ohrai, K.; Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 11737.
44. (e) See also: Wright, M. E.; Pulley, S. R. J. Org. Chem. 1989, 54, 2886.
45. Baraznenok, I. L.; Nenajdenko, V. G.; Balenkova, E. S. Tetrahedron 2000, 56, 3077.
46. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
47. Farina, V.; Krishnam, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
48. Farina, V.; Krishnam, B. J. Am. Chem. Soc. 1991, 113, 9585.
49. Farina, V.; Kapadia, S.; Krishnam, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.
50. +