Polymer supported formate in conjunction with commercial zinc dust provides a mild and efficient procedure for the reduction of organic azides to corresponding amines. A variety of alkyl and aryl azides were selectively reduced in high yield and purity at room temperature.
(a) LeyS.V., BaxendaleI.R., BreamR.N., JacksonP.S., LeachA.G., LongbottomD.A., NesiM., ScottJ.S., StorerR.I., and TaylorS.J., J. Chem. Soc. Perkin Trans.1, 2000, 3815; (b) A. Kirschning, H. Monenschein and R. Wittenberg, Angew. Chem. Int. Ed. Engl., 2001, 40, 650; (c) B. Clapham, T.S. Reger and K.D. Janda, Tetrahedron, 2001, 57, 4637; (d) J.A. Gladysz, Chem. Rev., 2002, 102, 3215; (e) S.V. Ley, I.R. Baxendale, G.Brusotti, M. Caldarelli, A. Massi and M. Nesi, Farmaco, 2002, 57, 321; (f) P. Hodge, Curr. Opin. Chem. Biol., 2003, 27, 362.
2.
(a) GonthierE., and BreinbauerR., Synlett, 2003, 1049; (b) G.A. Strohmeier and C.O. Kappe, Angew. Chem. Int. Ed. Engl., 2004, 43, 621; (c) J. Burt, T. Dean and S. Warriner, Chem. Commun., 2004, 454; (d) R.N. MacCoss, D.J. Henry, C.T. Brain and S.V. Ley, Synlett, 2004, 4, 675; (e) F.T. Coppo, K.A. Evans, T.L. Graybill and G. Burton, Tetrahedron Lett., 2004, 45, 3257; (f) M.K.W. Choi and P.H. Toy, Tetrahedron, 2004, 60, 2875 and references therein.
3.
(a) JasG., and KirschningA., Chem. Eur. J., 2003, 9, 5708; (b) C.K.Y. Lee, A.B. Holmes, S.V. Ley, I. McConvey, B. Al-Duri, G.A. Leeke, R.C.D. Santos and J.P.K. Seville, J. Chem. Soc., Chem. Commun., 2005, 16, 2175; (c) S.V. Ley, A. Massi, F. Rodríguez, D.C. Horwell, R.A. Lewthwaite, M.C. Pritchard and A.M. Reid, Angew. Chem. Int. Ed., 2001, 40, 1053.
4.
(a) SandeA.R., JagadaleM.H., ManeR.B., and SalunkheM.M., Tetrahedron Lett., 1984, 25, 3501; (b) A. Nag, A. Sarkar, S.K. Sarkar and K.P. Sunanda, Synth. Commun., 1987, 17, 1007; (c) N.M. Yoon, K.B. Park and Y.S. Gyoung, Tetrahedron Lett., 1983, 24, 5367.
5.
DelmondB., and DumartinG., Solid State Organometallic Chemistry: Methods and Applications: eds GielenM., WillemR., and WrackmeyerB., Wiley, Chichester1999, 5963.
6.
(a) RobertO., Hutchins, NataleN.R., and TafferI.M., J. Chem. Soc. Chem. Commun., 1978, 1088; (b) S.V Ley, M.H. Bolli, B. Hinzen, A.G. Gervois and B.J. Hall, J. Chem. Soc., Perkin Trans. I, 1998, 2239; (c) J. Habermann, S.V. Ley and J.S. Scott, J. Chem. Soc. Perkin Trans.1, 1998, 3127.
7.
UrabeH., and KuwajimaI., Tetrahedron Lett., 1983, 24, 5001.
8.
FirouzbadiH., and TamamiB., Synth. Commun., 1991, 21, 2275.
9.
(a) JohnstoneR.A.W., WilbyA.H., and EntwistleI.D., Chem. Rev., 1985, 85, 129; (b) B. Zacharie N. Moreau and C. Dockendorff, J. Org. Chem., 2001, 66, 5264; (c) S. Gowda, K. Abiraj and D.C. Gowda, Tetrahedron Lett., 2002, 43, 1329; (d) Z. Paryzek and H. Koenig, B. Tabaczka, Synthesis, 2003, 2023; (e) P.G. Reddy and S. Baskaran, Tetrahedron Lett., 2002, 43, 1919; (f) J.Q. Yu, H.C. Wu, C.R. Rao, J.B. Spencer and S.V. Ley, Chem. Commun., 2003, 678; (g) G.R. Srinivasa, K. Abiraj and D.C. Gowda, Tetrahedron Lett., 2003, 44, 5835; (h) K. Abiraj, G.R. Srinivasa and D.C. Gowda, Synlett, 2004, 877.
10.
(a) DesaiB., and DanksT.N., Tetrahedron Lett., 2001, 42, 5963; (b) B. Basu, M.M.H. Bhuiyan, P. Das and I. Hossain, Tetrahedron Lett., 2003, 44, 8931; (c) G.R. Srinivasa, K. Abiraj and D.C. Gowda, Indian J. Chem., 2006, 45, 297; (d) B. Basu, P. Das and S. Das, Molecular Diversity, 2005, 9, 259.
11.
AbirajK., SrinivasaG.R., and GowdaD.C., Int. J. Pep. Res. Therapeutics, 2005, 11, 153.
12.
SmithS.C., and HeathcockC.H., J. Org. Chem., 1992, 57, 6379.
13.
DonaldF.E., and DanishefskyS.J., J. Org. Chem., 1992, 57, 7001.
14.
(a) FringuelliF., PizzoF., and VaccaroL., Synthesis, 2000, 646; (b) I. Bosch, A.M. Costa, M. Martin and F. Urpi, J. Org. Lett., 2000, 2, 397; (c) J.H. Boyer, J. Am. Chem. Soc., 1951, 73, 586; (d) M. Vaultier, N. Knouzi and R. Carrie, Tetrahedron Lett., 1983, 24, 763; (e) F. Rolla, J. Org. Chem., 1982, 47, 4327; (f) W. Lin, X. Zhang, Z. He, Y. Jin, L. Gong and A. Mi, Synth. Commun. 2002, 32, 3279; (g) A. Koziara, K.O. Pacewicka, S. Zawadzki, A. Zwierzak, Synthesis, 1985, 202.
15.
SrinivasaG.R., NalinaK., AbirajK., and GowdaD.C., J. Chem. Res., 2003, 10, 630.
16.
BudavariS., O'NeilM.J., SmithA., HeckelmanP.E., The Merck Index 11th edn., Merck & Co., Inc., USA, 1989.
17.
VogelA.I., Text Book of Practical Organic Chemistry 5th edn., Addison Wesley Longman Limited, UK, 1997.
