Super fast cobalt carbonyl-mediated synthesis of ureas

Tetrahedron Letters

Volumn 46, Issue 19, 2005, Pages 3335-3339

  Enquist, Per Anders ^a   Nilsson, Peter ^a   Edin, Johan ^a   Larhed, Mats ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

Carbonylation; Cobalt carbonyl; Isocyanate; Microwave; Urea

Indexed keywords

AMINE; COBALT DERIVATIVE; ISOCYANIC ACID DERIVATIVE; UREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DENSITY; MICROWAVE IRRADIATION; REACTION TIME; SYNTHESIS;

EID: 17144405605     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.076     Document Type: Article

References (31)

1. M.B. Smith, and J. March March's Advanced Organic Chemistry. Reactions, Mechanisms, and Structure 5th ed. 2001 Wiley Interscience New York, Chichester, Brisbane, Toronto, Singapore
2. J.S. Nowick, D.L. Holmes, G. Noronha, E.M. Smith, T.M. Nguyen, and S.L. Huang J. Org. Chem. 61 1996 3929 3934
3. R.A. Batey, V. Santhakumar, C. Yoshina-Ishii, and S.D. Taylor Tetrahedron Lett. 39 1998 6267 6270
4. J.E. McCusker, A.D. Main, K.S. Johnson, C.A. Grasso, and L. McElwee-White J. Org. Chem. 65 2000 5216 5222
5. A. Bassoli, B. Rindone, S. Tollari, and F. Chioccara J. Mol. Catal. 60 1990 41 48
6. Y.J. Kim, and R.S. Varma Tetrahedron Lett. 45 2004 7205 7208
7. M.M. Mojtahedi, M.R. Saidi, and M. Bolourtchian J. Chem. Res. (S) 1999 710 711
8. D. Hunter J. Cell. Biochem. 2001 22 27
9. R.E. Dolle J. Comb. Chem. 6 2004 623 679
10. C.O. Kappe Angew. Chem., Int. Ed. 43 2004 6250 6284
11. M. Larhed, and A. Hallberg Drug Discov. Today 6 2001 406 416
12. M. Larhed, C. Moberg, and A. Hallberg Acc. Chem. Res. 35 2002 717 727
13. P.A. Enquist, P. Nilsson, and M. Larhed Org. Lett. 5 2003 4875 4878
14. N.F.K. Kaiser, U. Bremberg, M. Larhed, C. Moberg, and A. Hallberg J. Organomet. Chem. 603 2000 2 5
15. T. Morimoto, and K. Kakiuchi Angew. Chem., Int. Ed. 43 2004 5580 5588
16. Triethylamine, 1,2,2,6,6-pentamethylpiperidine (PMP) and NaOAc were investigated, but provided reduced yields
17. Propylene carbonate and water were added separately to investigate their impact on the reaction
18. Personal communication from Professor M. Beller
19. 2 + 4BHCl. See: I. Wender, H.W. Sternberg, and M. Orchin J. Am. Chem. Soc. 74 1952 1216 1219
20. J.L.J. Blanco, C.S. Barria, J.M. Benito, C.O. Mellet, J. Fuentes, F. Santoyo-Gonzalez, and J.M.G. Fernandez Synthesis 1999 1907 1914
21. F.E. Hong, and Y.C. Chang Organometallics 23 2004 718 729
22. B.S. Patil, G.R. Vasanthakumar, and V.V.S. Babu J. Org. Chem. 68 2003 7274 7280
23. K.G. Estep, C.E. Neipp, L.M.S. Stramiello, M.D. Adam, M.P. Allen, S. Robinson, and E.J. Roskamp J. Org. Chem. 63 1998 5300 5301
24. S.M. Hutchins, and K.T. Chapman Tetrahedron Lett. 35 1994 4055 4058
25. H.A. Duong, M.J. Cross, and J. Louie Org. Lett. 6 2004 4679 4681
26. R.A. Franz, F. Applegath, F.V. Morriss, and F. Baiocchi J. Org. Chem. 26 1961 3306 3308
27. M.K. Leung, J.L. Lai, K.H. Lau, H.H. Yu, and H.J. Hsiao J. Org. Chem. 61 1996 4175 4179
28. T.E. Stevens J. Org. Chem. 31 1966 2025 2026
29. K. Mashima, Y. Yamanaka, Y. Gohro, and A. Nakamura J. Organomet. Chem. 459 1993 131 138
30. R.A. Franz, F. Applegath, F.V. Morriss, F. Baiocchi, and L.W. Breed J. Am. Chem. Soc. 27 1962 4341 4346
31. H. Gross, and G. Zinner Chem. Ber. 106 1973 2315 2323