N-tert-Butoxycarbonylation of amines using H3PW12O40 as an efficient heterogeneous and recyclable catalyst

Tetrahedron Letters

Volumn 48, Issue 33, 2007, Pages 5865-5868

  Heydari, Akbar ^a   Shiroodi, Roohollah Kazem ^a   Hamadi, Hossein ^a   Esfandyari, Maryam ^a   Pourayoubi, Mehrdad ^a  

^a TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

(Boc)2O; Amine protection; Boc derivatives; Phosphotungstic acid

Indexed keywords

1,2 PHENYLENEDIAMINE; ACID; AMINE; AMINOALCOHOL; BICARBONATE; ESTER; LEWIS ACID; TUNGSTEN; YTTRIUM; ZIRCONIUM OXIDE;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL STRESS; OXIDATION; POLYMERIZATION; RACEMIZATION; REPRODUCIBILITY; SOLID PHASE SYNTHESIS; THERMOSTABILITY;

EID: 34447523478     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.064     Document Type: Article

References (62)

1. Satori G., Ballini R., Bigi F., Bosica G., Maggi R., and Righi P. Chem. Rev. 104 (2004) 199-250
2. Kocienski P.J. Protecting Groups (2000), George Thieme Verlag, Stuttgart, New York
3. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 2nd ed. (1999), Wiley, New York 503-550
4. Wuensch E. In: Mueller E., Bayer O., Meerwein H., and Ziegler K. (Eds). Houben-Weyl, Methods of Organic Chemistry. 4th ed. Vol. 15/1 (1974), George Thieme Verlag, Stuttgart 46
5. McOmie J.F.W. Protective Groups in Organic Chemistry (1973), Plenum Press, London
6. Gross E., and Meienhofer J. The Peptides Vol. 3 (1981), Academic Press, New York
7. Merrifield R.B. J. Am. Chem. Soc. 86 (1964) 304-305
8. Merrifield R.B. J. Am. Chem. Soc. 85 (1963) 2149-2154
9. Agami C., and Couty F. Tetrahedron 58 (2002) 2701-2724
10. Lutz C., Lutz V., and Knochel P. Tetrahedron 54 (1998) 6385-6402
11. Kim S., and Lee J.I. Chem. Lett. (1984) 237-238 and references cited therein
12. Guibe-Jampel E., and Wakselman M. Synthesis (1977) 772
13. Guibe-Jampel E., and Wakselman M. J. Chem. Soc., Chem. Commun. (1971) 267-271
14. Handy S.T., Sabatini J.J., Zhang Y., and Vulfova I. Tetrahedron Lett. 45 (2004) 5057-5060
15. Basel Y., and Hassner A. J. Org. Chem. 65 (2000) 6368-6380
16. Burk M.J., and Allen J.G. J. Org. Chem. 62 (1997) 7054-7057
17. Khalil E.M., Subasinghe N.L., and Johnson R.L. Tetrahedron Lett. 37 (1996) 2441-2444
18. Kelly T.A., and McNeil D.W. Tetrahedron Lett. 35 (1994) 9003-9006
19. Einhorn J., Einhorn C., and Luche J.-L. Synlett (1991) 37-38
20. Grehn L., and Ragnarsson U. Angew. Chem., Int. Ed. Engl. 24 (1985) 510-512
21. Chankeshwara S.V., and Chakraborti A.K. Org. Lett. 8 (2006) 3259-3262
22. Darnbrough S., Mervic M., Condon S.M., and Burns C.J. Synth Commun. 31 (2001) 3273-3280
23. Kelly T.A., and McNeil D.W. Tetrahedron Lett. 35 (1994) 9003
24. Knoelker H.-J., Braxmeier T., and Schlechtingen G. Synlett (1996) 502
25. Knoelker H.-J., and Braxmeier T. Tetrahedron Lett. 37 (1996) 5861-5864
26. Knoelker H.-J., Braxmeier T., and Schlechtingen G. Angew. Chem., Int. Ed. Engl. 34 (1995) 2497-2500
27. Sweet D.V. Registry of Toxic Effects of Chemical Substances 1985-86 (1988), US Govt. Printing Office, Washington, DC p 4049
28. Pandey R.K., Dagade S.P., Upadhyay R.K., Dongare M.K., and Kumar P. ARKIVOC 7 (2002) 28-33
29. Bartoli G., Bosco M., Locatelli M., Marcantoni E., Massaccesi M., Melchiorre P., and Sambri L. Synlett 10 (2004) 1794-1798
30. Heydari A., and Hosseini S.E. Adv. Synth. Catal. 347 (2005) 1929-1932
31. Sharma G.V., Reddy J.J., Lakshmi P.S., and Krishna P.R. Tetrahedron Lett. 45 (2004) 6963-6965
32. Chankeshwara S.V., and Chakraborti A.K. Tetrahedron Lett. 47 (2006) 1087-1091
33. Chakraborti A.K., and Chankeshwara S.V. Org. Biomol. Chem. 4 (2006) 2769-2771
34. Chankeshwara S.V., and Chakraborti A.K. J. Mol. Catal. A 253 (2006) 198-202
35. Niimi K.-J., Serita S., Hiraoka T., and Yokozawa T. Tetrahedron Lett. 41 (2000) 7075-7078
36. Kobayashi S., Araki M., and Yasuda M. Tetrahedron Lett. 36 (1995) 5773-5776
37. Kobayashi S., Akiyama R., Kawamura H., and Ashitani H. Chem. Lett. (1977) 1039-1041
38. Timofeeva M.N. Appl. Catal. A: Gen. 256 (2003) 19-35
39. Kozhevnikov I.V. Catalysis by Polyoxometalates Vol. 2 (2002), Wiley, Chichester
40. Okuhara T., Mizuno N., and Misono M. Appl. Catal. A: Gen. 222 (2001) 63-77
41. Moffat J.B. Metal-Oxygen Clusters. The Surface and Catalytic Properties of Heteropoly Oxometallates (2001), Kluwer, New York
42. Kozhevnikov I.V. Chem. Rev. 98 (1998) 171-198
43. Corma A. Chem. Rev. 95 (1995) 559-614
44. Misosno M., and Nojiri N. Appl. Catal. 64 (1990) 1-30
45. Okuhara T., Mizuno M., and Misono M. Adv. Catal. 46 (1996) 113-252
46. Heteropolyacids have been reported as versatile green catalysts for a variety of reactions such as: synthesis of 3,4-dihydropyrimidin-2(1H)-ones:. Mishra B.G., Kumar D., and Rao V.S. Catal. Commun. 7 (2006) 457-459
47. deprotection of t-butyldimethylsilane:. Kumar G.D., and Bhaskaran S. J. Org. Chem. 70 (2005) 4520-4523
48. regioselective aerobic oxygenation of nitrobenzene to 2-nitrophenol:. Khenkin A.M., Weiner L., and Neumann R. J. Am. Chem. Soc. 127 (2005) 9988-9989
49. oxidation of aliphatic, benzylic and allylic alcohols using DMSO as oxygen transfer agent:. Khenkin A.M., and Neumann R. J. Org. Chem. 67 (2002) 7075-7079
50. dehydration of alcohols:. Okuhara T., Nishimura T., and Misono M. Chem. Lett. (1995) 155-156
51. esterifications:. Hu C., Hashimoto M., Okuhara T., and Misono M. J. Catal. 143 (1993) 437-443
52. de-esterification:. Okuhara T., Nishimura T., Ohashi K., and Misoni M. Chem. Lett. (1990) 1201-1202
53. hydration of olefins:. Yamada Y. Peterotech 13 (1990) 627-632
54. etherification:. Okuhara T., Kasai A., and Misono M. Shokubai (Catalyst) 22 (1980) 226-228
55. Liu J.H., Peng J., and Wang E.B. J. Mol. Struct. 525 (2000) 71-77
56. Crans D.C., Mahroof-Tahir M., and Aderson O. Inorg. Chem. 33 (1994) 5586-5590
57. Attanasio D., Bonamico M., and Fares V. J. Chem. Soc., Dalton Trans. (1990) 3221-3228
58. Peng J., Wang E.B., and Zhou Y.S. J. Chem. Soc., Dalton Trans. (1990) 3865-3869
59. You E., Wang E.B., and He Q.L. J. Mol. Struct. (2000) 133-139
60. Porta F., Cenini S., Pizzotti M., and Crotti C. Gazz. Chim. Ital. 115 (1985) 275-280
61. Pozdnev V.F. Int. J. Peptide Protein Res. 40 (1992) 407-414
62. Kawamura K., Horikiri H., Hayakawa J., Seki C., Yoshizawa K., Umeuchi H., and Nagase H. Chem. Pharm. Bull. 52 (2004) 670-674