NHC-iron-catalyzed aerobic oxidative aromatic esterification of aldehydes using boronic acids

Organic Letters

Volumn 12, Issue 12, 2010, Pages 2686-2689

  Rosa, Joao N ^a   Reddy, R Sudarshan ^a   Candeias, Nuno R ^a   Cal, Pedro M S D ^a   Gois, Pedro M P ^a  

^a RESEARCH INSTITUTE FOR MEDICINES IMED ULISBOA   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMIDE; BENZOIC ACID DERIVATIVE; BORONIC ACID DERIVATIVE; CARBENE; DRUG DERIVATIVE; FERROUS ION; METHANE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ESTERIFICATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALDEHYDES; AMIDES; BENZOATES; BORONIC ACIDS; CATALYSIS; ESTERIFICATION; FERROUS COMPOUNDS; METHANE; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 77953592111     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100302e     Document Type: Article

References (45)

1. González, S. D.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612
2. Hahn, F. E. Angew. Chem., Int. Ed. 2006, 45, 1348
3. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290
4. N-Heterocyclic Carbenes in Transition Metal Catalysis. In Topics in Organometallic Chemistry; Glorius, F., Ed.; Springer: Berlin, Heidelberg, 2007; Vol. 21.
5. N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, 2006.
6. Enthaler, S.; Junge, K.; Beller, M. Angew. Chem. 2008, 47, 3317
7. Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 114, 6217
8. Fürstner, A. Angew. Chem., Int. Ed. 2009, 48, 1364
9. Czaplik, W. M.; Mayer, M.; Cvengrš, J.; von Wangelin, A. J. ChemSusChem 2009, 2, 396
10. Scepaniak, J. J.; Youg, J. A.; Bontchev, R. P.; Smith, J. M. Angew. Chem., Int. Ed. 2009, 48, 1364
11. Liu, B.; Xia, Q.; Chen, W. Angew. Chem., Int. Ed. 2009, 48, 5513
12. Danopoulos, A. A.; Wright, J. A.; Motherwell, W. B. Chem. Commun. 2005, 784
13. Louie, J.; Grubbs, R. H. Chem. Commun. 2000, 1479
14. McGuinness, D. S.; Gibson, V. C.; Steed, J. W. Organometallics 2004, 23, 6288
15. Hatakeyama, T.; Nakamura, M. J. Am. Chem. Soc. 2007, 129, 9844
16. Plietker, B.; Dieskau, A.; Möws, K.; Jatsch, A. Angew. Chem., Int. Ed. 2008, 47, 198
17. Hatakeyama, T.; Hashimoto, S.; Ishizuka, K.; Nakamura, M. J. Am. Chem. Soc. 2009, 131, 11949
18. Gois, P. M. P.; Trindade, A. F.; Veiros, L. F.; Andre, V.; Duarte, M. T.; Afonso, C. A. M.; Caddick, S.; Cloke, F. G. N. Angew. Chem., Int. Ed. 2007, 46, 5750
19. Trindade, A. F.; Gois, P. M. P.; Veiros, L. F.; Andre, V.; Duarte, M. T.; Afonso, C. A. M.; Caddick, S.; Cloke, F. G. N. J. Org. Chem. 2008, 73, 1076
20. Esposito, O.; Gois, P. M. P.; Lewis, A. K.; de, K.; Caddick, S.; Cloke, F. G. N.; Hitchcock, P. B. Organometallics 2008, 27, 6411
21. Gomes, L. F. R.; Trindade, A. F.; Candeias, N. R.; Gois, P. M. P.; Afonso, C. A. M. Tetrahedron Lett. 2008, 49, 7372
22. Kovi, K. E.; Wolf, C. Chem.-Eur. J. 2008, 14, 6302
23. Wu, X.-F.; Darcel, C. Eur. J. Org. Chem. 2009, 1144
24. Qin, C.; Wu, H.; Chen, J.; Liu, M.; Cheng, J.; Su, W.; Ding, J. Org. Lett. 2008, 10, 1537
25. Sarvari, M. H.; Sharghi, H. Tetrahedron 2005, 61, 10903
26. Tamaddon, F.; Amrollahi, M. A.; Sharafat, L. Tetrahedron Lett. 2005, 46, 7841
27. Shah, S. T. A.; Khan, K. M.; Hussain, H.; Anwar, M. U.; Fecker, M.; Voelter, W. Tetrahedron 2005, 61, 6652
28. Oohashi, Y.; Fukumoto, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2005, 78, 1508
29. Olah, G. A.; Wang, Q.; Trivedi, N. J.; Prakash, G. K. S. Synthesis 1991, 739
30. Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V. Chem. Lett. 2004, 33, 248
31. Kotsuki, H.; Arimura, K.; Araki, T.; Shinohara, T. Synlett 1999, 462
32. Toda, F.; Yagi, M.; Kiyoshige, K. J.Chem. Soc., Chem. Commun. 1988, 958
33. Selected examples
34. Li, Y. Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem., Int. Ed. 2009, 48, 3817
35. Li, Z.; Yu, R.; Li, H. Angew. Chem., Int. Ed. 2008, 47, 7497
36. Shi, F.; Tse, M. K.; Li, Z.; Beller, M. Chem.-Eur. J. 2008, 14, 8793
37. Nakanishi, M.; Bolm, C. Adv. Synth. Catal. 2007, 349, 861
38. Meyer, N. J.; Lough, A. J.; Morris, R. H. Chem.-Eur. J. 2009, 15, 5605
39. Zou, T.; Pi, S.-S.; Li, J. H. Org. Lett. 2009, 11, 453
40. Selected examples
41. Yu, H.; Fu, Y.; Guo, Q.; Lin, Z. Organometallics 2009, 28, 4443
42. Popp, B. V.; Wendlandt, J. E.; Landis, C. R.; Stahl, S. S. Angew. Chem. 2007, 46, 601
43. Gligorich, K. M.; Sigman, M. S. Chem. Commun. 2009, 3854
44. Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221
45. Urkan, K. B.; Sigman, M. S. Angew. Chem., Int. Ed. 2009, 48, 3146