Use of silver carbonate in the Wittig reaction

Journal of Organic Chemistry

Volumn 78, Issue 23, 2013, Pages 12224-12228

  Jedinak, Lukas ^a   Rush, Latoya ^a   Lee, Mijoon ^a   Hesek, Dusan ^a   Fisher, Jed F ^a   Boggess, Bill ^a   Noll, Bruce C ^a   Mobashery, Shahriar ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC ALDEHYDES; BASIC CONDITIONS; EFFICIENT SYNTHESIS; PHOSPHORUS YLIDES; ROOM TEMPERATURE; SILVER CARBONATE; WITTIG OLEFINATION; WITTIG REACTION;

KETONES; SILVER;

CHEMICAL REACTIONS;

ALDEHYDE; CARBONIC ACID; CARBONYL DERIVATIVE; KETONE; PHOSPHORUS; SILVER; SILVER CARBONATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; OLEFINATION; ROOM TEMPERATURE; SYNTHESIS; WITTIG REACTION;

ALKENES; CARBONATES; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SILVER COMPOUNDS;

EID: 84890226714     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401972a     Document Type: Article

References (36)

1. Kolodiazhny, O. I. Phosphorus Ylides: Chemistry and Application in Organic Synthesis; Wiley: New York, 1999.
2. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R.; Aliphatic Compounds: Vogel's Textbook of Practical Organic Chemistry; Longman Scientific & Technical: Harlow, 1980.
3. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W.; Toshiya, S. Tetrahedron Lett. 1984, 25, 2183-2186
4. Blasdel, L. K.; Myers, A. G. Org. Lett. 2005, 7, 4281-4283
5. Ando, K.; Oishi, T.; Masahiro, H.; Ohno, H.; Ibuka, T. J. Org. Chem. 2000, 65, 4745-4749
6. Rübsam, F.; Antje, M. E.; Michel, C.; Giannis, A. Tetrahedron 1997, 53, 1707-1714
7. Lu, Y.; Arndtsen, B. A. Org. Lett. 2009, 11, 1369-1372
8. Kao, T.-T.; Syu, S.-e.; Jhang, Y.-W.; Lin, W. Org. Lett. 2010, 12, 3066-3069
9. Antonioletti, R.; Bonadies, R.; Ciammaichella, A.; Viglianti, A. Tetrahedron 2008, 64, 4644-4648
10. Taber, D. F.; Nelson, C. G. J. Org. Chem. 2006, 71, 8973-8974
11. Lee, M.; Hesek, D.; Mobashery, S. J. Org. Chem. 2005, 70, 367-369
12. Bonadies, F.; Cardilli, A.; Lattanzi, A.; Orelli, L. R.; Scettri, A. Tetrahedron Lett. 1994, 35, 3383-3386
13. Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624-2626
14. El-Batta, A.; Jiang, C.; Zhao, W.; Annes, R.; Cooksy, A. L.; Bergdahl, M. J. Org. Chem. 2007, 72, 5244-5259
15. Simoni, D.; Rossi, M.; Rondanin, R.; Mazzali, A.; Baruchello, R.; Malagutti, C.; Roberti, M.; Invidiata, F. P. Org. Lett. 2000, 2, 3765-3768
16. Chintareddy, V. R.; Ellern, A.; Verkade, J. G. J. Org. Chem. 2010, 75, 7166-7174
17. Balema, P. V.; Wiench, J. W.; Pruski, M.; Pecharsky, V. K. J. Am. Chem. Soc. 2002, 124, 6244-6245
18. McNulty, J.; Das, P.; McLeod, D. Chem.-Eur. J. 2010, 16, 6756-6760
19. McNulty, J.; McLeod, D. Chem.-Eur. J. 2011, 17, 8794-8798
20. Rémond, E.; Bayardon, J.; Ondel-Eymin, M.-J.; Jugé, S. J. Org. Chem. 2012, 77, 7579-7587
21. Padrón, J. M.; Kokotos, G.; Martín, T.; Markidis, T.; Gibbons, W. A.; Martín, V. S. Tetrahedron: Asymmetry 1998, 9, 3381-3394
22. Vicente, J.; Chicote, M. T.; Saura-Llamas, I.; Jones, P. G. Organometallics 1989, 8, 767-770
23. Vicente, J.; Chicote, M. T.; Fernandez-Baeza, J.; Martin, J.; Saura-Llamas, I.; Turpin, J.; Jones, P. G. J. Organomet. Chem. 1987, 331, 409-421
24. Fackler, J. Sci. Synth. 2004, 3, 663-690
25. Kapferer, T.; Brückner, R. Eur. J. Org. Chem. 2006, 2119-2133
26. Xu, Ch.; Liu, Y.; Huang, B.; Li, H.; Qin, X.; Zhang, X.; Dai, Y. Appl. Surf. Sci. 2011, 257, 8732-8736
27. Imashiro, R.; Seki, M. J. Org. Chem. 2004, 69, 4216-4226
28. Mu, B.; Li, T.; Xu, W.; Zeng, G.; Lu, P.; Wu, Y. Tetrahedron 2007, 63, 11475-11488
29. Aggarwal, V. K.; Fulton, J. R.; Sheldon, C. G.; Vicente, J. J. Am. Chem. Soc. 2003, 125, 6034-6035
30. Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Pipko, S. E.; Shivanyuk, A. N.; Tolmachev, A. A. J. Comb. Chem. 2007, 9, 1073-1078
31. Elgendy, E. M.; Khayyat, S. H. Russ. J. Org. Chem. 2008, 44, 823-829
32. Angle, S. R.; Choi, I.; Tham, F. S. J. Org. Chem. 2008, 73, 6268-6278
33. McNulty, J.; Keskar, K. Tetrahedron Lett. 2008, 49, 7054-7057
34. Fu, Z.; Huang, S.; Su, W.; Hong, M. Org. Lett. 2010, 12, 4992-4995
35. Zeni, G.; Alves, D.; Braga, A. L.; Stefani, H. A.; Nogueira, C. W. Tetrahedron Lett. 2004, 45, 4823-4826
36. Skoric, I.; Marinic, Z.; Molcanov, K.; Kojic-Prodic, B.; Sindler-Kulyk, M. Magn. Reson. Chem. 2007, 45, 680-684