Rh 2(OAc) 4/CeCl 3-catalyzed olefination of carbonylferrocenes with α-diazocarbonyl compounds: A convenient synthesis of alkenylferrocenes

Synlett

Volumn 23, Issue 6, 2012, Pages 943-947

  Chen, Shufeng ^a   Zhang, Lele ^a   Du, Yan ^a   Li, Baoguo ^a  

^a INNER MONGOLIA UNIVERSITY   (China)

Author keywords

alkenylferrocene; carbonylferrocenes; diazo compounds; olefination

Indexed keywords

ALKENYLFERROCENE; ALPHA DIAZOCARBONYL COMPOUND; AZO COMPOUND; CARBONYL DERIVATIVE; CARBONYLFERROCENE; CESIUM CHLORIDE; COPPER ACETATE; COPPER COMPLEX; COPPER IODIDE; DIAZOACETIC ACID ETHYL ESTER; FERRIC CHLORIDE; FERROCENE DERIVATIVE; FERROCENECARBOXALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; METHODOLOGY; OLEFINATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 84862782947     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290612     Document Type: Article

References (46)

1. Togni A, Hayashi T, Ferrocenes VCH New York 1995
2. Atkinson R C. J., Gibson V C., Long N J., Chem. Soc. Rev. 2004 33 213
3. Green M L. H., Marder S R., Thompson M E., Bandy J A., Bloor D, Kolinsky P V., Jones R J., Nature (London) 1987 330 360
4. Togni A, Angew. Chem., Int. Ed. Engl. 1996 35 1475
5. Richards C J., Locke A J., Tetrahedron: Asymmetry 1998 9 2377
6. Dai L X., Tu T, You S L., Deng W P., Hou X L., Acc. Chem. Res. 2003 36 659
7. Thomas J C., Chem. Rev. 2003 103 3101
8. Arrayas R G., Adrido J, Carretero J C., Angew. Chem. Int. Ed. 2006 45 7674
9. Moyano A, Rios R, Synlett 2009 1863
10. Sondenecker A, Cvengros J, Aardoom R, Togni A, Eur. J. Org. Chem. 2011 78
11. Barlow S, Marder S R., In Functional Organic Materials Müller T J. J. Bunz U H. F. Wiley-VCH Weinheim 2007 393-437
12. Kato S.-i, Beels M T. R., La Porta P, Schweizer W B., Boudon C, Gisselbrecht J.-P, Biaggio I, Diederich F, Angew. Chem. Int. Ed. 2010 49 6207
13. Hudson S A., Maitlis P M., Chem. Rev. 1993 93 861
14. Ferrocenes: Homogenous Catalysis. Organic Synthesis. Materials Science Togni A Hayshi T VCH Weinheim 1995
15. Long N J., Metallocenes 1st. ed. Blackwell Science London 1997
16. Sutclie O B., Bryce M R., Tetrahedron: Asymmetry 2003 14 2297
17. Kadkin O N., Han H, Galyametdinov Y G., J. Organomet. Chem. 2007 692 5571
18. Ochi Y, Suzuki M, Imaoka T, Murata M, Nishihara H, Einaga Y, Yamamoto K, J. Am. Chem. Soc. 2010 132 5061
19. Molina P, Pastor A, Vilaplana M J., Velasco M D., Ramirez de Arellano M C., Organometallics 1997 16 5836
20. Molina P, Tarraga A, Lopez J L., Martinez J C., J. Organomet. Chem. 1999 584 147
21. Bollo S, Vergara L J., Bonta M, Chauviere G, Perie J, Squella J A., Electroanal. Chem. 2001 511 46
22. Van Staveren D R., Metzler-Nolte N, Chem. Rev. 2004 104 5931
23. Fouda M F. R., Abd-Elzaher M M., Abdelsamaia R A., Labib A A., Appl. Organomet. Chem. 2007 21 613
24. Buriez O, Heldt J M., Labbe E, Vessieres A, Jaouen G, Amatore C, Chem. Eur. J. 2008 14 8195
25. Metzler-Nolte N, Salmain M, In Ferrocenes: Ligands, Materials and Biomolecules Stepnicka P Wiley New York 2008 499
26. Patra M, Gasser G, Wenzel M, Merz K, Bandow J E., Metzler-Nolte N, Organometallics 2010 29 4312
27. Debroy P, Roy S, Coord. Chem. Rev. 2007 251 203
28. Rodriguez J.-G, Gayo M, Fonseca I, J. Organomet. Chem. 1997 534 35
29. Thomas K R. J., Lin J T., Wen Y S., J. Organomet. Chem. 1999 575 301
30. Mata J A., Falomir E, Llusar R, Peris E, J. Organomet. Chem. 2000 616 80
31. Mata J A., Uriel S, Llusar R, Peris E, Organometallics 2000 19 3797
32. Hradsky A, Bildstein B, Schuler N, Schottenberger H, Jaitner P, Ongania K.-H, Wurst K, Launay J.-P, Organometallics 1997 16 392
33. Chesney A, Bryce M R., Batsanov A S., Howard J A. K., Goldenberg L M., Chem. Commun. 1998 677
34. Stepnicka P, Lamac M, Cisarova I, J. Organomet. Chem. 2008 693 446
35. Granzhan A, Teulade-Fichou M.-P, Tetrahedron 2009 65 1349
36. Blakemore P R., Ho D K. H., Nap W M., Org. Biomol. Chem. 2005 3 1365
37. Jary W G., Mahler A.-K, Purkathofer T, Baumgartner J, J. Organomet. Chem. 2001 629 208
38. Kasahara A, Izumi T, Maemura M, Bull. Chem. Soc. Jpn. 1977 50 1021
39. Naskar D, Das S K., Giribabu L, Maiya B G., Roy S, Organometallics 2000 19 1464
40. Kundu A, Prabhakar S, Vairamani M, Roy S, Organometallics 1997 16 4796
41. Jong S.-J, Fang J.-M, J. Org. Chem. 2001 66 3533
42. Sinha P, Roy S, Chem. Commun. 2001 1798
43. Debroy P, Roy S, J. Organomet. Chem. 2003 675 105
44. For comprehensive reviews about transition-metal-catalyzed olefinations of aldehydes or ketones with diazo compounds, see:, Doyle M P., McKervey M A., Ye T, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds Wiley-Interscience New York 1998
45. Herrmann W A., Olefins from Aldehydes in Applied Homogeneous Catalysis with Organometallic Compounds 2nd ed., Vol. 3 Wiley-VCH Weinheim 2002 1078-1086
46. Zhang Z, Wang J, Tetrahedron 2008 64 6577