Nano-γ-Fe2O3: Efficient, Reusable and Green Catalyst for N-tert-Butoxycarbonylation of Amines in Water


An efficient and versatile practical protocol for the chemoselective N-tert-butoxycarbonylation of amines using Nano-γ-Fe2O3 and (BOC)2O. Nano-γ-Fe2O3 was applied as an efficient, green, heterogeneous and reusable catalyst at ambient temperature; the method is general for the preparation of N-Boc derivatives of aliphatic, heterocyclic, aromatic as well as amino acid derivatives.

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Medisetti, V. , Parimi, U. , Babu Anagani, R. and V. V. V. Satyanarayana, K. (2014) Nano-γ-Fe2O3: Efficient, Reusable and Green Catalyst for N-tert-Butoxycarbonylation of Amines in Water. Green and Sustainable Chemistry, 4, 95-101. doi: 10.4236/gsc.2014.42014.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] Ballini, R., Bigi, F., Bosica, G., Maggi, R., Satori, G. and Righi, P. (2004) Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis. Chemical Reviews, 104, 199-250.
[2] Wuensch, E. (1974) Houben-Weyl Methods of Organic Chemistry. In: Mueller, E., Bayer, O. and Ziegler, K., Eds., Methods of Organic Chemistry, 4th Edition, George Thieme, Stuttgart, 46.
[3] Wuts, P.G.M. and Greene, T.W., Protective Groups in Organic Synthesis (1999) Greene’s Protective Groups in Organic Synthesis. 2nd Edition, Wiley, New York, 503.
[4] Yamamoto, Y., Tarbell, D.S. and Pope, B.M. (1972) New Method to Prepare N-t-Butoxycarbonyl Derivatives and the Corresponding Sulfur Analogs from di-t-Butyl Dicarbonate or di-t-Butyl Dithiol Dicarbonates and Amino Acids. Proceedings of the National Academy of Sciences of the USA, 69, 730-732.
[5] Itoh, M., Hagiwara, D. and Kamiya, T. (1977) Peptides. VI. Some Oxime Carbonates as Novel t-Butoxycarbonylating Reagents. Bulletin of the Chemical Society of Japan, 50, 718-721.
[6] Wilson, I.B. and Harris, R.B. (1983) Synthesis of tert-Butyl Aminocarbonate, a New Type of Compound That Can Be Used to Acylate Amines. Tetrahedron Letters, 24, 231-232.
[7] Hansen, J.B., Nielsen, M.C., Ehrbar, U. and Buchradt, O. (1982) Partially Protected Polyamines. Synthesis, 1982, 404-405.
[8] Fali, C.N., Li, J., Katritzsky, A.R., Ager, D.J. and Prakash, I. (1997) Synthesis of 1-(T-Butoxycarbonyl)benzotriazole and 1-(p-Methoxybenzyloxycarbonyl)benzotriazole and Their Use in the Protection of Amino Acids. Synthetic Communications, 27, 1623-1630.
[9] Hassner, A. and Basel, Y.J. (2000) Di-tert-Butyl Dicarbonate and 4-(Dimethylamino)pyridine Revisited. Their Reactions with Amines and Alcohols. Organic Chemistry, 65, 6368-6380.
[10] Burk, M.J. and Allen, J.G. (1997) A Mild Amide to Carbamate Transformation. The Journal of Organic Chemistry, 62, 7054-7057.
[11] Kelly, T.A. and McNeil, D.W. (1994) A Simple Method for the Protection of Aryl Amines as Their t-Butylcarbamoyl (Boc) Derivatives. Tetrahedron Letters, 35, 9003-9006.
[12] Senet, J.-P., Barcelo, G. and Sennyey, G. (1986) Alkyl 1-Chloroalkyl Carbonates: Reagents for the Synthesis of Carbamates and Protection of Amino Group. Synthesis, 8, 627-632.
[13] Kamiya, T., Itoh, M. and Hagiwara, D. (1975) Synthesis of Cyclo(L-Pro-L-Tyr) from the t-BOC Derivative of L-Proline. Tetrahedron Letters, 49, 4393-4394.
[14] Reddy, J.J., Lakshmi, P.S., Sharma, G.V.S. and Krishna, P.R. (2004) Rapid and Facile Lewis Acid Catalysed Boc Protection of Amines. Tetrahedron Letters, 45, 6963-6965.
[15] Heydari, A. and Hosseini, S.E. (2005) Lithium Perchlorate-Catalyzed Boc Protection of Amines and Amine Derivatives. Advanced Synthesis & Catalysis, 347, 1929-1932.
[16] Chakraborti, A.K. and Chankeshwara, S.V. (2006) HClO4-SiO2 as a New, Highly Efficient, Inexpensive and Reusable Catalyst for N-tert-Butoxycarbonylation of Amines. Organic & Biomolecular Chemistry, 4, 2769-2771.
[17] Prabhakar, P., Reddy, S.T., Rajesh, K., Suryakiran, N. and Venkateswarlu, Y. (2006) Facile N-tert-Butoxycarbonylation of Amines Using La(NO3)3·6H2O as a Mild and Efficient Catalyst under Solvent-Free Conditions. Tetrahedron Letters, 47, 8039-8042.
[18] Chankeshwara, S.V. and Chakraborti, A.K. (2006) Montmorillonite K 10 and Montmorillonite KSF as New and Reusable Catalysts for Conversion of Amines to N-tert-Butylcarbamates. Journal of Molecular Catalysis A: Chemical, 253, 198-202.
[19] Heydari, A., Khaksar, S., Tajbakhsh, M. and Vahdat, S.M. (2008) Hydrogen Bond Catalyzed Chemoselective N-tert-Butoxycarbonylation of Amines. Tetrahedron Letters, 49, 3527-3529.
[20] Siskin, M., Katritzky, A.R. and Allin, S.M. (1996) Aquathermolysis: Reactions of Organic Compounds with Superheated Water. Accounts of Chemical Research, 29, 399-406.
[21] Boyle, T.J., Burton, P.D., Peterson, E.J. and Datye, A.K. (2010) Synthesis of High Surface Area ZnO(0001) Plates as Novel Oxide Supports for Heterogeneous Catalysts. Catalysis Letters, 139, 26-32.

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