Palladium-catalyzed decarboxylative sp3-sp3 coupling of nitrobenzene acetic esters

Journal of the American Chemical Society

Volumn 129, Issue 48, 2007, Pages 14860-14861

  Waetzig, Shelli R ^a   Tunge, Jon A ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; NITROBENZENE ACETIC ESTER DERIVATIVE; NITROBENZENE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; DECARBOXYLATION; DRUG STRUCTURE; STOICHIOMETRY;

ACETIC ACID; CATALYSIS; DECARBOXYLATION; ESTERS; LIGANDS; MOLECULAR STRUCTURE; NITROBENZENES; PALLADIUM;

EID: 36849051972     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077070r     Document Type: Article

References (21)

1. (a) The Nitro Group in Organic Synthesis; Ono, N., Ed.; Wiley-VCH: New York. 2001.
2. (b) Hoogenraad, M.; van der Linden, J. B.; Smith, A. A. Org. Proc. Res. Dev. 2004, 8, 469.
3. Rayabarapu, D. K.; Tunge, J. A. J. Am. Chem. Soc. 2005, 127, 13510.
4. (a) Gooßen, L. J.; Rodriguez, N.; Melzer, B.; Linder, C.; Deng, G.; Levy, L. M. J. Am. Chem. Soc. 2007, 129, 4824.
5. (b) Gooßen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662.
6. (a) Myers, A. G.; Tanaka, D.; Mannion, M. R. J. Am. Chem. Soc. 2002, 124, 11250.
7. (b) Tanaka, D.; Romeril, S. P.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 10323.
8. (a) Fu, G.; Saito, B. J. Am. Chem. Soc. 2007, 129, 9602.
9. (b) Dongol, K. G.; Koh, H.; Sau, M.; Chai, C. L. L. Adv. Synth. Catal. 2007, 349, 1015.
10. (c) Frisch, A. C.; Beller, M. Angew. Chem. Int. Ed. 2005, 44, 674.
11. (d) Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Org. Lett. 2005, 7, 3805.
12. Waetzig, S. R.; Tunge, J. A. J. Am. Chem. Soc. 2007, 129, 4138.
13. (a) Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 4113.
14. (b) Mohr, J. T.; Behenna, D. C.; Harned, A. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2005, 44, 6924.
15. (c) Trost, B. M.; Xu, J. J. Am. Chem. Soc. 2005, 127, 17180.
16. (d)You, S-L.; Dai, L-X. Angew. Chem, Int. Ed. 2006, 45, 5246.
17. (e) Waetzig, S. R.; Rayabarapu, D. K.; Weaver, J. D.; Tunge, J. A. Angew. Chem., Int. Ed. 2006, 45, 4977.
18. Protodecarboxylation of nitrobenzene acetic acids: (a) Bull, D. J.; Fray, M. J.; Mackenny, M. C.; Malloy, K. A. Synlett 1996, 647.
19. (b) Ioussaini, O.; Capedevielle, P.; Maumy, M. Tetrahedron 1984, 40, 3229.
20. (c) J. Chem. Soc. 1938, 1186.
21. A similar effect on the decarboxylation of nitroarenes was recently observed, but not explained. Imao, D.; Itoi, A.; Yamazaki, A.; Shirakura, M.; Ohtoshi, R.; Ogata, K.; Ohmori, Y.; Ohta, T.; Ito, Y. J. Org. Chem. 2007, 72, 1652.