Chemoselective conversion of α-unbranched aldehydes to amides, esters, and carboxylic acids by NHC-catalysis

Chemical Communications

Volumn 48, Issue 1, 2012, Pages 145-147

  Kuwano, Satoru ^a   Harada, Shingo ^a   Oriez, Raphaël ^a   Yamada, Ken Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AMIDE; CARBENE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION;

EID: 82355163624     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c1cc15539c     Document Type: Article

References (30)

1. D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606.
2. N. Marion, S. Díez-González, S. P. Nolan, Angew. Chem. Int. Ed. 2007, 46, 2988.
3. V. Nair, S. Vellalath, B. P. Babu, Chem. Soc. Rev. 2008, 37, 2691.
4. K. Y.-K. Chow, J. W. Bode, J. Am. Chem. Soc. 2004, 126, 8126.
5. N. T. Reynolds, J. Read de Alaniz, T. Rovis, J. Am. Chem. Soc. 2004, 126, 9518.
6. A. Chan, K. A. Scheidt, Org. Lett. 2005, 7, 905.
7. K. Zeitler, Org. Lett. 2006, 8, 637.
8. B. Alcaide, P. Almendros, G. Cabrero, M. P. Ruiz, Chem. Commun. 2007, 4788.
9. H. U. Vora, T. Rovis, J. Am. Chem. Soc. 2007, 129, 13796.
10. J. W. Bode, S. S. Sohn, J. Am. Chem. Soc. 2007, 129, 13798.
11. G.-Q. Li, L.-X. Dai, S.-L. You, Org. Lett. 2009, 11, 1623.
12. Y. Kawanaka, E. M. Phillips, K. A. Scheidt, J. Am. Chem. Soc. 2009, 131, 18028.
13. K. Thai, L. Wang, T. Dudding, F. Bilodeau, M. Gravel, Org. Lett. 2010, 12, 5708.
14. K. B. Ling, A. D. Smith, Chem. Commun. 2011, 47, 373.
15. J. Qi, X. Xie, J. He, L. Zhang, D. Ma, X. She, Org. Biomol. Chem. 2011, 9, 5948.
16. B. E. Maki, A. Chan, E. M. Phillips, K. A. Scheidt, Org. Lett. 2007, 9, 371.
17. B. E. Maki, K. A. Scheidt, Org. Lett. 2008, 10, 4331.
18. B. E. Maki, A. Chan, E. M. Phillips, K. A. Scheidt, Tetrahedron, 2009, 65, 3102.
19. M. Yoshida, Y. Katagiri, W.-B. Zhu, K. Shishido, Org. Biomol. Chem. 2009, 7, 4062.
20. S. De Sarkar, S. Grimme, A. Studer, J. Am. Chem. Soc. 2010, 132, 1190.
21. S. De Sarkar, A. Studer, Org. Lett. 2010, 12, 1992.
22. M. S. Kerr, J. R. de Alaniz, T. Rovis, J. Org. Chem. 2005, 70, 5725.
23. T. Kano, H. Mii, K. Maruoka, J. Am. Chem. Soc. 2009, 131, 3450.
24. M. J. P. Vaismaa, S. C. Yau, N. C. O. Tomkinson, Tetrahedron Lett. 2009, 50, 3625.
25. K. Gambar'jan, Zh. Obshch. Khim. 1933, 3, 222.
26. T. C. Bruice, N. G. Kundu, J. Am. Chem. Soc. 1966, 88, 4098.
27. T. C. Owen, A. Richards, J. Am. Chem. Soc. 1987, 109, 2520.
28. R. J. Mahatthananchai, P. Zheng, J. W. Bode, Angew. Chem. Int. Ed. 2011, 50, 1673.
29. M. Movassaghi, M. A. Schmidt, Org. Lett. 2005, 7, 2453.
30. I. Koppel, J. Koppel, I. Leito, V. Pihl, L. Grehn, U. Ragnarsson, J. Chem. Res. Miniprint, 1993, 11, 3008.