The direct synthesis of N-alkylated amides via a tandem hydration N-alkylation reaction from nitriles, aldoximes and alcohols

Chemical Communications

Volumn 50, Issue 61, 2014, Pages 8303-8305

  Wang, Nana ^a   Zou, Xiaoyuan ^a   Ma, Juan ^a   Li, Feng ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDOXIME; AMIDE; BENZONITRILE; BENZYL ALCOHOL; NITRILE; COORDINATION COMPOUND; IRIDIUM; OXIME;

ALKYLATION; ARTICLE; HYDRATION; SYNTHESIS; CATALYSIS; CHEMISTRY;

ALCOHOLS; ALKYLATION; AMIDES; CATALYSIS; COORDINATION COMPLEXES; IRIDIUM; NITRILES; OXIMES;

EID: 84903974214     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc02742f     Document Type: Article

References (27)

1. T. Cupido, J. Tulla-Puche, J. Spengler, F. Albericio, Curr. Opin. Drug Discovery Dev. 2007, 10, 768.
2. C. L. Allen, J. M. J. Williams, Chem. Soc. Rev. 2011, 40, 3405.
3. M. B. Smithand. J. March, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Wiley, Hoboken, NJ, 6th edn, 2007.
4. M. B. Smith, Organic Synthesis, Mc-Graw-Hill Companies, New York, 2nd edn, 2002.
5. C. Gunanathan, Y. Ben-David, D. Milstein, Science, 2007, 317, 790.
6. L. U. Nordstrom, H. Vogt, R. Madsen, J. Am. Chem. Soc. 2008, 130, 17672.
7. J. H. Dam, G. Osztrovszky, L. U. Nordstrom, R. Madsen, Chem. – Eur. J. 2010, 16, 6820.
8. S. C. Ghosh, S. Muthaiah, Y. Zhang, X. Xu, S. H. Hong, Adv. Synth. Catal. 2009, 351, 2643.
9. S. Muthaiah, S. C. Ghosh, J. E. Jee, C. Chen, J. Zhang, S. H. Hong, J. Org. Chem. 2010, 75, 3002.
10. C. Chen, Y. Zhang, S. H. Hong, J. Org. Chem. 2011, 76, 10005.
11. I. S. Makarov, P. Fristrup, R. Madsen, Chem. – Eur. J. 2012, 18, 15683.
12. A. Nova, D. Balcells, N. D. Schley, G. E. Dobereiner, R. H. Crabtree, O. Eisenstein, Organometallics, 2010, 29, 6548.
13. N. D. Schley, G. E. Dobereiner, R. H. Crabtree, Organometallics, 2011, 30, 4174.
14. F. Li, P. Qu, J. Ma, X. Zou, C. Sun, ChemCatChem, 2013, 5, 2178.
15. B. Kang, Z. Fu, S. H. Hong, J. Am. Chem. Soc. 2013, 135, 11704.
16. J. J. Ritter, P. P. Minieri, J. Am. Chem. Soc. 1948, 70, 4045.
17. F. R. Benson, J. J. Ritter, J. Am. Chem. Soc. 1949, 71, 4128.
18. H. Plaut, J. J. Ritter, J. Am. Chem. Soc. 1951, 73, 4076.
19. J. Lee, M. Kim, S. Chang, H. Y. Lee, Org. Lett. 2009, 11, 5598.
20. E. S. Kim, H. S. Kim, J. N. Kim, Tetrahedron Lett. 2009, 50, 2973.
21. E. S. Kim, H. S. Lee, S. H. Kim, J. N. Kim, Tetrahedron Lett. 2010, 51, 1589.
22. X. Ma, Y. He, Y. Hu, M. Lu, Tetrahedron Lett. 2012, 53, 449.
23. X. Ma, Y. He, P. Wang, M. Lu, Appl. Organomet. Chem. 2012, 26, 377.
24. F. Li, H. Shan, L. Chen, Q. Kang, P. Zou, Chem. Commun. 2012, 48, 603.
25. F. Li, C. Sun, H. Shan, X. Zou, J. Xie, ChemCatChem, 2013, 5, 1543.
26. C. Sun, X. Zou, F. Li, Chem. – Eur. J. 2013, 19, 14030.
27. P. Qu, C. Sun, J. Ma, F. Li, Adv. Synth. Catal. 2014, 356, 447.