Insertion of benzyne into the Pd-C bond. Synthesis of unnatural amino acid derivatives by sequential insertion of benzyne and CO: 2,2'-functionalized biaryls containing alkylamino and carboxymethyl substituents. Isolation of stable carbopalladated-benzyne intermediates

Chemical Communications

Volumn 48, Issue 53, 2012, Pages 6744-6746

  Garcia López, José Antonio ^a   Oliva Madrid, Maria José ^a   Saura Llamas, Isabel ^a   Bautista, Delia ^a   Vicente, José ^a  

^a UNIVERSITY OF MURCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AROMATIC HYDROCARBON; BENZYNE; CARBON MONOXIDE; HOMOVERATRYLAMINE; PALLADIUM; PHENTERMINE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; CHEMICAL BOND; CHEMICAL PARAMETERS; CHEMICAL REACTION;

EID: 84862197914     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc32975a     Document Type: Article

References (41)

1. J. L. Henderson, A. S. Edwards, M. F. Greaney, J. Am. Chem. Soc., 2006, 128, 7426
2. C. Xie, Y. Zhang, Z. Huang, X. Xu, J. Org. Chem., 2007, 72, 5431
3. J. L. Henderson, A. S. Edwards, M. F. Greaney, Org. Lett., 2007, 9, 5589
4. N. Chatani, A. Kamitani, M. Oshita, Y. Fukumoto, S. Murai, J. Am. Chem. Soc., 2001, 123, 12686
5. T. T. Jayanth, M. Jeganmohan, C.-H. Cheng, J. Org. Chem., 2004, 69, 8445
6. T. T. Jayanth, C.-H. Cheng, Chem. Commun., 2006, 894
7. I. Quintana, A. J. Boersma, D. Peña, D. Pérez, E. Guitián, Org. Lett., 2006, 8, 3347
8. D. Peña, D. Pérez, E. Guitián, Chem. Rec., 2007, 7, 326
9. Z. Liu, R. C. Larock, Angew. Chem. Int. Ed., 2007, 46, 2535
10. C. Xie, Y. Zhang, Y. Yang, Chem. Commun., 2008, 4810
11. S. Bhuvaneswari, M. Jeganmohan, C.-H. Cheng, Chem. Commun., 2008
12. J. P. Waldo, X. Zhang, F. Shi, R. C. Larock, J. Org. Chem., 2008, 73, 6679
13. H. Yoshida, T. Morishita, H. Nakata, J. Ohshita, Org. Lett., 2009, 11, 373
14. T. Gerfaud, L. Neuville, J. Zhu, Angew. Chem., Int. Ed., 2009, 48, 572
15. S. A. Worlikar, R. C. Larock, Org. Lett., 2009, 11, 2413
16. Y.-L. Liu, Y. Liang, S.-F. Pi, X.-C. Huang, J.-H. Li, J. Org. Chem., 2009, 74, 3199
17. T. Morishita, H. Yoshida, J. Ohshita, Chem. Commun., 2010, 46, 640
18. Y. Lin, L. Wu, X. Huang, Eur. J. Org. Chem., 2011, 2993
19. G. Domínguez, J. Pérez-Castells, Chem. Soc. Rev., 2011, 40, 3430
20. Z. Liu, R. C. Larock, J. Org. Chem., 2007, 72, 223
21. E. Yoshikawa, Y. Yamamoto, Angew. Chem. Int. Ed., 2000, 39, 173
22. E. Yoshikawa, K. V. Radhakrishnan, Y. Yamamoto, J. Am. Chem. Soc., 2000, 122, 7280
23. S. Bhuvaneswari, M. Jeganmohan, C.-H. Cheng, Org. Lett., 2006, 8, 5581
24. J. Cámpora, A. Llebaría, J. M. Moretó, M. L. Poveda, E. Carmona, Organometallics, 1993, 12, 4032
25. A. A. Cant, L. Roberts, M. F. Greaney, Chem. Commun., 2010, 46, 8671
26. J. Vicente, I. Saura-Llamas, J. A. García-López, D. Bautista, Organometallics, 2010, 29, 4320
27. J. Vicente, I. Saura-Llamas, D. Bautista, Organometallics, 2005, 24, 6001
28. M.-J. Oliva-Madrid, J. A. García-López, I. Saura-Llamas, D. Bautista, J. Vicente, Organometallics, 2012, 31, 3647
29. F. Szemes, A. Rybar, D. Uhrin, E. Solcaniova, Chem. Pap., 1991, 45, 667
30. P. Appukkuttan, E. Van der Eycken, Eur. J. Org. Chem., 2008, 5867
31. R. G. Miller, D. P. Kuhlman, J. Organomet. Chem., 1971, 26, 401
32. Y. Sato, Y. Kobayashi, M. Sugiura, H. Shirai, J. Org. Chem., 1978, 43, 199
33. D. Seyferth, D. P. Duncan, M. L. Shannon, E. W. Goldman, Organometallics, 1984, 3, 574
34. D. Seyferth, S. C. Vick, M. L. Shannon, Organometallics, 1984, 3, 1897
35. M. A. Bennett, M. R. Kopp, E. Wenger, A. C. Willis, J. Organomet. Chem., 2003, 667, 8
36. M. Retbøll, A. J. Edwards, A. D. Rae, A. C. Willis, M. A. Bennett, E. Wenger, J. Am. Chem. Soc., 2002, 124, 8348
37. M. A. Bennett, T. Dirnberger, D. C. R. Hockless, E. Wenger, A. C. Willis, J. Chem. Soc.Dalton Trans., 1998, 271
38. N. Suzuki, D. Hashizume, Coord. Chem. Rev., 2010, 254, 1037
39. N. E. Schore, Chem. Rev., 1988, 88, 1081
40. M. Lautens, W. Klute, W. Tam, Chem. Rev., 1996, 96, 49
41. S. Saito, Y. Yamamoto, Chem. Rev., 2000, 100, 2901