Highly regioselective palladium-catalyzed methoxycarbonylation of styrene using chiral ferrocene- and biphosphole-based ligands

Tetrahedron Letters

Volumn 49, Issue 35, 2008, Pages 5186-5189

  Diab, Lisa ^a,b   Gouygou, Maryse ^a   Manoury, Eric ^a   Kalck, Philippe ^b   Urrutigoïty, Martine ^b  

^a CNRS   (France)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

Enantioselectivity; Methoxycarbonylation; P,P ligands; P,S ligands; Palladium; Regioselectivity; Vinylarenes

Indexed keywords

BISPHOSPHOLE DERIVATIVE; FERROCENE DERIVATIVE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; STYRENE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; ISOMERISM; RACEMIZATION; STEREOCHEMISTRY;

EID: 47049096984     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.057     Document Type: Article

References (48)

1. Boivin T.L. Tetrahedron 43 (1987) 3309-3362
2. In: Colqhoun H.M., Thompson D.J., and Twiggs M.V. (Eds). Carbonylation (1991), Plenum Press, New York
3. Beller, M., Ed., Topics in Organomet. Chem.: Catalytic Carbonylations, 2006, 18.
4. Sonawane H., Bellur N.S., Ahuja J.R., and Kulkarni D.G. Tetrahedron: Asymmetry 3 (1992) 163-192
5. Rieu J.-P., Boucherle A., Cousse H., and Mouzin G. Tetrahedron 42 (1986) 4095-4131
6. In: Gerharzt W. (Ed). Ullmann's Encyclopedia of Industrial Chemistry Vol. 3 (1985), VCH, Weinheim 41
7. del Rio I., Claver C., and van Leeuwen P.W.N.M. Eur. J. Inorg. Chem. (2001) 2718-2719
8. van Leeuwen P.W.N.M., Zuideveld M.A., Swennenhuis B.H.G., Freixa Z., Kamer P.C.J., Goubitz K., Fraanje J., Lutz M., and Spek A.L. J. Am. Chem. Soc. 125 (2003) 5523-5539
9. Donald S.M.A., McGregor S.A., Settels V., Cole-Hamilton D.J., and Eastham G.R. Chem. Commun. (2007) 562-564
10. Guiu E., Caporali M., Munoz B., Muller C., Lutz M., Spek A.L., Claver C., and van Leeuwen P.W.N.M. Organometallics 25 (2006) 3102-3104
11. Ooka H., Inoue T., Itsuno S., and Tanaka M. Chem. Commun. (2005) 1173-1175
12. Aguirre P.A., Lagos C.A., Moya S.A., Zuniga C., Vera-Oyarce C., Sola E., Peris G., and Bayon J.C. Dalton Trans. (2007) 5419-5426
13. Gouygou M., Tissot O., Daran J.C., and Balavoine G.G.A. Organometallics 16 (1997) 1008-10015
14. Tissot O., Gouygou M., Daran J.-C., and Balavoine G.G.A. Organometallics 17 (1998) 5927-5930
15. Tissot O., Hydrio J., Gouygou M., Dallemer F., Daran J.-C., and Balavoine G.G.A. Tetrahedron 56 (2000) 85-93
16. Malacea R., Manoury E., Routaboul L., Daran J.-C., Poli R., Dunne J.P., Withwood A.C., Godard C., and Duckett S.B. Eur. J. Inorg. Chem. (2006) 1803-1816
17. Malacea R., Daran J.-C., Duckett S.B., Dunne J.P., Manoury E., Poli R., and Withwood A.C. Dalton Trans. (2006) 3350-3359
18. Robé E., Hegedus C., Bakos J., Coppel Y., Daran J.-C., and Gouygou M. Inorg. Chim. Acta 361 (2008) 1861-1867
19. Tissot O., Gouygou M., Dallemer F., Daran J.-C., and Balavoine G.G.A. Eur. J. Inorg. Chem. (2001) 2385-2389
20. Le Roux E., Malacea R., Manoury E., Poli R., Gonsalvi L., and Peruzzini M. Adv. Synth. Catal. 349 (2007) 309-313
21. Diab L., Gouygou M., Manoury E., Kalck P., and Urrutigoïty M. J. Mol. Catal. A: Chem. 278 (2007) 102-106
22. Robé, E.; Hegedus, C.; Bakos, J.; Daran, J.-C.; Gouygou, M. Organometallics, submitted for publication.
23. Ortega C., Gouygou M., and Daran J.-C. Chem. Commun. (2003) 1154-1155
24. Malacea R., Routaboul L., Manoury E., Daran J.-C., and Poli R. J. Organomet. Chem. 693 (2008) 1469-1477
25. Diab L., Daran J.-C., Gouygou M., Manoury E., and Urrutigoïty M. Acta Crystallogr., Sect. C 64 (2008) m43-m45
26. Manoury E., Fossey J.S., Aït-Haddou H., Daran J.-C., and Balavoine G.G.A. Organometallics 19 (2000) 3736-3739
27. Tissot O., Gouygou M., Dallemer F., Daran J.-C., and Balavoine G.G.A. Angew. Chem., Int. Ed. 40 (2001) 1076-1078
28. Mourgues S., Serra D., Lamy F., Vincendeau S., Daran J.-C., Manoury E., and Gouygou M. Eur. J. Inorg. Chem. (2003) 2820-2826
29. Robé E., Ortéga C., Mikina M., Mikolajczyk M., Daran J.-C., and Gouygou M. Organometallics 24 (2005) 5549-5559
30. Routaboul L., Vincendeau S., Daran J.-C., and Manoury E. Tetrahedron: Asymmetry 16 (2005) 2685-2690
31. Mateus N., Routaboul L., Daran J.-C., and Manoury E. J. Organomet. Chem. 691 (2006) 2297-2310
32. Lopez Cortes J.G., Ramon O., Vincendeau S., Serra D., Lamy F., Daran J.-C., Manoury E., and Gouygou M. Eur. J. Inorg. Chem. (2006) 5148-5157
33. Vavasori A., Toniolo T., and Cavinato G. J. Mol. Catal. 191 (2003) 9-21
34. Munoz B., Marinetti A., Ruiz A., Castillon S., and Claver C. Inorg. Chem. Commun. 8 (2005) 1113-1115
35. Godard C., Ruiz A., and Claver C. Helv. Chim. Acta 89 (2006) 1610-1622
36. Diab L., Daran J.-C., Gouygou M., Manoury E., and Urrutigoïty M. Acta Crystallogr., Sect. C 63 (2007) m586-m588
37. Cometti G., and Chiusoli G.P. J. Organomet. Chem. 236 (1982) C31-C32
38. Zhou H., Lu S., Hou J., Chen J., Fu H., and Wang H. Chem. Lett. (1996) 339
39. Zhou H., Hou J., Cheng J., Lu S., Fu H., and Wang H. J. Organomet. Chem. 543 (1997) 227-228
40. Oi S., Nomura M., Aiko T., and Inoue Y. J. Mol. Catal. A: Chem. 115 (1997) 289-295
41. Nozaki K., Lakshmi-Kantam M., Horiuchi T., and Takaya H. J. Mol. Catal. A: Chem. 118 (1997) 247-253
42. Wang L., Kwok W.H., Chan A.S.C., Tu T., Hou X., and Dai L. Tetrahedron: Asymmetry 14 (2003) 2291-2295
43. Kewu Y., and Xuanzhen J. Chem. J. Internet (2005) 7
44. Munoz B.K., Godard C., Marinetti A., Ruiz A., Benet-Buchholz J., and Claver C. Dalton Trans. (2007) 3350-3359
45. Godard C., Munoz B.K., Ruiz A., and Claver C. Dalton Trans. (2008) 853-860
46. 2 atmosphere using Schlenk techniques. Immediately after addition of the substrate (0.1 ml, 0.86 mmol), the solution was introduced into the autoclave, and then heated and pressurized with CO. After 24 h, the autoclave was cooled and slowly depressurized. After separation by column chromatography (CC), the solution was analyzed by GC, using tetradecane as internal standard, and the ee was determined by chiral GC.
47. Diab, L. Ph.D. Thesis 2007, Université Paul Sabatier, Toulouse, France.
48. Robé E., Perlikowska W., Lemoine C., Diab L., Vincendeau S., Mikolajczyk M., Daran J.-C., and Gouygou M. Dalton Trans. (2008) 2894-2898