Xphos ligand and platinum catalysts: A versatile catalyst for the synthesis of functionalized β-(E)-vinylsilanes from terminal alkynes

Journal of Organometallic Chemistry

Volumn 693, Issue 16, 2008, Pages 2789-2797

  Hamze, Abdallah ^a,b   Provot, Olivier ^a,b   Brion, Jean Daniel ^a,b   Alami, Mouâd ^a,b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

Author keywords

Alkynes; Hydrosilylation; Phosphane ligands; Platinum; Regioselectivity

Indexed keywords

ACETYLENE; CATALYSTS; CHELATION; CHEMICAL REACTIONS; HYDROCARBONS; HYDROSILYLATION; PLATINUM; PORT TERMINALS;

ARYLALKYNES; FUNCTIONALIZED; PLATINUM CATALYSTS; SYNTHESIS (OF CHIRAL IONIC LIQUIDS); TERMINAL ALKYNES; VINYL SILANES;

CATALYSIS;

EID: 47249163643     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.05.028     Document Type: Article

References (57)

1. Trost B.M., and Ball Z.T. Synthesis (2005) 853-887
2. Marciniec B. Comprehensive Handbook on Hydrosilylation (1992), Pergamon Press, Oxford
3. Hiyama T., and Kusumoto T. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis vol. 8 (1991), Pergamon Press, Oxford 763
4. For recent other catalytic methods leading to the synthesis of β-(E)-vinylsilanes, see:. Marciniec B., and Pietraszuk C. In: Grubbs R.H. (Ed). Handbook of Metathesis (2003), Wiley-VCH, Weinheim (Chapter 2.13)
5. Kim M., Park S., Maifeld S.V., and Lee D. J. Am. Chem. Soc. 126 (2004) 10242-10243
6. Pietraszuk C., Fischer H., Rogalski S., and Marciniec B. J. Organomet. Chem. 690 (2005) 5912-5921
7. Pi J.H., and Huang X. Tetrahedron Lett. 45 (2004) 2215-2218
8. Itami K., Nokami T., and Yoshida J.-I. Tetrahedron 57 (2001) 5045-5054
9. Kwan M.L., Yeung C.W., Breno K.L., and Doxsee K.M. Tetrahedron Lett. 42 (2001) 1411-1413
10. Hiyama T. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-coupling Reactions (1998), Wiley-VCH, New York 421-453
11. Denmark S.E., and Ober M.H. Aldrichim. Acta 36 (2003) 75-85
12. Handy C.J., Manoso A.S., McElroy W.T., Seganish W.M., and DeShong P. Tetrahedron 61 (2005) 12201-12225
13. Flann J., and Overman L.E. J. Am. Chem. Soc. 109 (1987) 6115-6118
14. Oku J., Taksuchi M., Saito A., and Asami R. Polym. J. 24 (1992) 1409-1417
15. Trost B.M., and Ball Z.T. J. Am. Chem. Soc. 127 (2005) 17644-17655
16. Maifeld S.V., Tran M.N., and Lee D. Tetrahedron Lett. 46 (2005) 105-108
17. Na Y., and Chang S. Org. Lett. 2 (2000) 1887-1889
18. Sridevi V.S., Fan W.Y., and Leong W.K. Organometallics 26 (2007) 1157-1160
19. Takeuchi R., Nitta S., and Watanabe D. J. Org. Chem. 60 (1995) 3045-3051
20. Faller J.W., and D'Alliessi D.G. Organometallics 21 (2002) 1743-1746
21. Sato A., Kinoshita H., Shinokubo H., and Oshima K. Org. Lett. 6 (2004) 2217-2220
22. Zeng J.Y., Hsieh M.H., and Lee H.M. J. Organomet. Chem. 690 (2005) 5662-5671
23. Miyake Y., Isomura E., and Iyoda M. Chem. Lett. 35 (2006) 836-837
24. Motoda D., Shinokubo H., and Oshima K. Synlett (2002) 1529-1531
25. Lewis L.N., Sy K.G., Bryant G.L., and Donahue P.E. Organometallics 10 (1991) 3750-3759
26. Chauhan M., Hauck J., Keller L.P., and Boudjouk P. J. Organomet. Chem. 645 (2002) 1-13
27. Wang F., and Neckers D.C. J. Organomet. Chem. 665 (2003) 1-6
28. De BO G., Berthon-Gelloz G., Tinant B., and Marko I.E. Organometallics 25 (2006) 1881-1890
29. Wu W., and Li C.-J. Chem. Commun. (2003) 1668-1669
30. Green M., Spencer J.L., Gordon F., Stone A., and Tsipis C.A. J. Chem. Soc., Dalton Trans. (1977) 1525-1529
31. Tsipis C.A. J. Organomet. Chem. 187 (1980) 427-446
32. Murphy P.J., Spencer J.L., and Procter G. Tetrahedron Lett. 31 (1990) 1051-1054
33. Tsipis C.A. J. Organomet. Chem. 188 (1980) 53-61
34. Denmark S.E., and Wang Z. Org. Lett. 3 (2001) 1073-1076
35. Itami K., Mitsudo K., Nishino A., and Yoshida J.-I. J. Org. Chem. 67 (2002) 2645-2652
36. Aneetha H., Wu W., and Verkade J. Organometallics 24 (2005) 2590-2596
37. Wang H.W., Cheng Y.J., Chen C.H., Lim T.S., Fann W., Lin C.L., Chang Y.P., Lin K.C., and Luh T.Y. Macromolecules 40 (2007) 2666-2671
38. Nicolaou K.C., Nold A.L., Milbum R.R., Schindler C.S., Cole K.P., and Yamaguchi J. J. Am. Chem. Soc. 129 (2007) 1760-1768
39. Barbero A., Blanco Y., García C., and Pulido F.J. Synthesis (2000) 1223-1228
40. Lo M.Y., and Sellinger A. Synlett (2006) 3009-3012
41. Hamze A., Provot O., Alami M., and Brion J.-D. Org. Lett. 7 (2005) 5625-5628
42. Hamze A., Provot O., Brion J.-D., and Alami M. Synthesis (2007) 2025-2036
43. A portion of this study has been communicated:. Hamze A., Provot O., Brion J.-D., and Alami M. Tetrahedron Lett. 49 (2008) 2429-2431
44. Liron F., Le Garrec P., and Alami M. Synlett (1999) 246-248
45. Alami M., Liron F., Gervais M., Peyrat J.F., and Brion J.D. Angew. Chem., Int. Ed. 41 (2002) 1578-1580
46. Liron F., Gervais M., Peyrat J.F., Alami M., and Brion J.D. Tetrahedron Lett. 44 (2003) 2789-2794
47. For the hydrostannation of enynes and related compounds see:. Alami M., and Ferri F. Synlett (1996) 755-756
48. Ferri F., and Alami M. Tetrahedron Lett. 37 (1996) 7971-7974
49. Bujard M., Ferri F., and Alami M. Tetrahedron Lett. 39 (1998) 4243-4246
50. Hamze A., Provot O., Brion J.-D., and Alami M. J. Org. Chem. 72 (2007) 3868-3874
51. Trost B.M., Machacek M.R., and Ball Z.T. Org. Lett. 5 (2003) 1895-1898
52. 2 is a fast and quantitative reaction. For spectroscopic data of Xphos ligand, see:. Huang X., Anderson K.W., Zim D., Jiang L., Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 125 (2003) 6653-6655
53. Sugimoto M., Yamazaki I., Mizoe N., Anzai M., and Sakaki S. Theor. Chem. Acc. 102 (1999) 377-384
54. Murata M., Watanabe S., and Masuda Y. Tetrahedron Lett. 40 (1999) 9255-9257
55. Marciniec B., Maciejewski H., and Kownacki I.J. Mol. Catal. A 135 (1998) 223-231
56. Battace A., Zair T., Doucet H., and Santelli M.J. Organomet. Chem. 690 (2005) 3790-3802
57. Adams R.D., Cortopassi J.E., and Pompeo M.P. Organometallics 11 (1992) 1-2