One-Pot Direct Synthesis of Weinreb Amides from Aryl and Hetero Aryl Halides Using Co 2(CO) 8 as an Effective CO Source under Conventional Thermal Heating

Synthetic Communications

Volumn 45, Issue 4, 2015, Pages 531-538

  Baburajan, Poongavanam ^a   Elango, Kuppanagounder P ^a  

^a GANDHIGRAM RURAL UNIVERSITY   (India)

Author keywords

Aryl halides; carbonylation; Co2(CO)8; palladiumacetate; Weinrebamides

Indexed keywords

AMIDE; BASE; CARBON DIOXIDE; CARBONYL DERIVATIVE; HALIDE; HYDROXYLAMINE; UNCLASSIFIED DRUG; WEINREB AMIDE;

AMINOCARBONYLATION; ARTICLE; CARBONYLATION; COMPARATIVE STUDY; HEATING; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; REACTION OPTIMIZATION; TEMPERATURE;

EID: 84945180014     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2014.974610     Document Type: Article

References (29)

1. Sibi, M. P. Org. Prep. Proced. Int. 1993, 25, 15
2. Jackson, M.; Leverett, C.; Toczko, J. F.; Roberts, J. C. J. Org. Chem. 2002, 67, 5032
3. Khlestkin, D. G.; Mazhukin, D. G. Curr. Org. Chem. 2003, 7, 967
4. Murphy, J. A.; Commeureuc, A.; Snaddon, T. N.; McGuire, T. M.; Khan, T. A.; Hisler, K.; Dewis, M. L.; Carling, R. Org. Lett. 2005, 7, 1427
5. Hisler, K.; Tripoli, R.; Murphy, J. A. Tetrahedron Lett. 2006, 47, 6293.
6. Nahm, S.; Weinreb, S. M. Tedrahedron Lett. 1981, 22, 3815.
7. Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001
8. Chin-Kang, S.; Shih-Jung, H.; Zhuang-ping, Z. J. Org. Chem. 2002, 67, 831.
9. Braun, M.; Waldmuller, D. Synthesis 1989, 856
10. Niu, T.; Zhang, W.; Huang, D.; Xu, C.; Wang, H.; Yulai, Hu. Org. Lett. 2009, 11, 4474
11. Woo, J. C. S.; Fenster, E.; Dake, G. R. J. Org. Chem. 2004, 69, 8984.
12. Murakami, M.; Hoshino, Y.; Ito, H.; Ito, Y. Chem. Lett. 1998, 163.
13. Martinelli, J. R.; Freckmann, D. M.; Buchwald, S. L. Org. Lett. 2006, 8, 4843.
14. Deagostino, A.; Larini, P.; Occhiato, E. G.; Pizzuto, L.; Prandi, C.; Venturello, P. J. Org. Chem. 2008, 73, 1941.
15. Wannberg, J.; Larhed, M. J. Org. Chem. 2003, 68, 5750
16. Wu, X.; Larhed, M. Org. Lett. 2005, 7, 3327
17. Wu, X.; Wannberg, J.; Larhed, M. Tetrahedron 2006, 62, 4665
18. Wan, Y.; Alterman, M.; Larhed, M.; Hallberg, A. J. Org. Chem. 2002, 67, 6232
19. Luke, R.; Russo, F.; Larhed, M. Synlett 2012, 23, 685.
20. Wieckowska, A.; Fransson, R.; Odell, L. R.; Larhed, M. J. Org. Chem. 2011, 76, 978.
21. Baburajan, P.; Senthilkumaran, R.; Elango, K. P. New J. Chem. 2013, 37, 3050
22. Baburajan, P.; Elango, K. P. Tetrahedron Lett. 2014, 55, 1006
23. Baburajan, P.; Elango, K. P. Tetrahedron Lett. 2014, 55, 3525.
24. Bickelhaupt, M. F.; Koning, L. J.; Nibberling, M. J. Org. Chem. 1993, 58, 2436
25. Graham, S. L.; Scholz, T. H. Tetrahedron Lett. 1990, 31, 6269.
26. Nielsen, S.; Smith, G.; Begtrup, M.; Kristensen, J. Chem-Eur. J. 2010, 16, 4557
27. Spencer, J.; Rathnam, R. P.; Patel, H.; Anjum, N. Tetrahedron 2008, 64, 10195
28. Nielsen, S. D.; Smith, G.; Begtrup, M.; Kristensen, J. L. Eur. J. Org. Chem. 2010, 3704
29. Iyer, S.; Kulkarni, G. M. Synth. Commun. 2004, 34, 721.