Olefination reactions using tetraarylphosphonium (TAP)-supported phosphorus ylides

Synthesis

Volumn , Issue 14, 2011, Pages 2275-2280

  Lebel, Hélène ^a   Davi, Michaël ^a   Roy, Marie Noelle ^a   Zeghida, Walid ^a   Charette, André B ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

alkenes; diazo compounds; green chemistry; Wittig reaction; ylides

Indexed keywords

DIAZO COMPOUNDS; GREEN CHEMISTRY; OLEFINATION REACTION; PHOSPHONATES; PHOSPHORUS YLIDES; WITTIG REACTION; YLIDES;

AMIDES; OLEFINS; PHOSPHORUS; PHOSPHORUS COMPOUNDS;

CHEMICAL REACTIONS;

ALKENE DERIVATIVE; AMIDE; AZO COMPOUND; COPPER; DIAZO COMPOUND; ESTER; OXIDE; PHOSPHINE OXIDE; PHOSPHONIC ACID DERIVATIVE; PHOSPHONIUM DERIVATIVE; PHOSPHORUS DERIVATIVE; PHOSPHORUS YLIDE DERIVATIVE; TETRAARYLPHOSPHONIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; GREEN CHEMISTRY; OLEFINATION; REACTION ANALYSIS; WITTIG REACTION;

EID: 79960139728     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260065     Document Type: Article

References (39)

1. Takeda T, Modern Carbonyl Olefination Wiley-VCH Weinheim 2004
2. Wittig G, Geissler G, Liebigs Ann. Chem. 1953 580 44
3. Wittig G, Schöllkopf U, Chem. Ber. 1954 87 1318
4. Nicolaou K C., Harter M W., Gunzner J L., Nadin A, Liebigs Ann. Chem. 1997 1283
5. Murphy P J., Lee S E., J. Chem. Soc., Perkin Trans. 1 1999 3049
6. Rein T, Pedersen T M., Synthesis 2002 579
7. Ramazani A, Kazemizadeh A R., Ahmadi E, Noshiranzadeh N, Souldozi A, Curr. Org. Chem. 2008 12 59
8. Constable D J. C., Dunn P J., Hayler J D., Humphrey G R., Leazer J L., Linderman R J., Lorenz K, Manley J, Pearlman B A., Wells A, Zaks A, Zhang T Y., Green Chem. 2007 9 411
9. Clarke S D., Harrison C R., Hodge P, Tetrahedron Lett. 1980 21 1375
10. Bernard M, Ford W T., J. Org. Chem. 1983 48 326
11. Bernard M, Ford W T., Nelson E C., J. Org. Chem. 1983 48 3164
12. Sieber F, Wentworth P, Toker J D., Wentworth A D., Metz W A., Reed N N., Janda K D., J. Org. Chem. 1999 64 5188
13. Westman J, Org. Lett. 2001 3 3745
14. Fairlamb I J. S., ChemSusChem 2009 2 1021
15. Marsden S P., Nat. Chem. 2009 1 685
16. OBrien C J., Tellez J L., Nixon Z S., Kang L J., Carter A L., Kunkel S R., Przeworski K C., Chass G A., Angew. Chem. Int. Ed. 2009 48 6836
17. Leung P S. W., Teng Y, Toy P H., Org. Lett. 2010 12 4996
18. Poupon J C., Boezio A A., Charette A B., Angew. Chem. Int. Ed. 2006 45 1415
19. Zoute L, Lacombe C, Quirion J C., Charette A B., Jubault P, Tetrahedron Lett. 2006 47 7931
20. Kuhn F E., Santos A M., Mini-Rev. Org. Chem. 2004 1 55
21. Lebel H, Paquet V, J. Am. Chem. Soc. 2004 126 320
22. Sun W, Kuhn F E., Appl. Catal., A 2005 285 163
23. Sun W, Yu B S., Kuhn F E., Tetrahedron Lett. 2006 47 1993
24. Pedro F M., Santos A M., Baratta W, Kuhn F E., Organometallics 2007 26 302
25. Lebel H, Ladjel C, Organometallics 2008 27 2676
26. Lebel H, Davi M, Diez-Gonzalez S, Nolan S P., [nl]J. Org. Chem. 2007 72 144
27. Lebel H, Ladjel C, Brethous L, J. Am. Chem. Soc. 2007 129 13321
28. Lebel H, Parmentier M, Org. Lett. 2007 9 3563
29. Lebel H, Davi M, Adv. Synth. Catal. 2008 350 2352
30. Lebel H, Davi M, Stoklosa G T., J. Org. Chem. 2008 73 6828
31. Davi M, Lebel H, Org. Lett. 2009 11 41
32. Shriver D F., Drezdzon M A., The Manipulation of Air-Sensitive Compounds Wiley New York 1986
33. Searle N E., Org. Synth. Coll. Vol. IV Wiley New York 1963 424
34. Bartlett P A., Carruthers N I., Winter B M., Long K P., J. Org. Chem. 1982 47 1284
35. Ohira S, Synth. Commun. 1989 19 561
36. Still W C., Kahn M, Mitra A, J. Org. Chem. 1978 43 2923
37. Artuso E, Barbero M, Degani I, Dughera S, Fochi R, Tetrahedron 2006 62 3146
38. Rai R, Katzenellenbogen J A., J. Med. Chem. 1992 35 4150
39. Felluga F, Pitacco G, Valentin E, Venneri C D., Tetrahedron: Asymmetry 2008 19 945