Synlett 2014; 25(4): 515-518
DOI: 10.1055/s-0033-1340550
letter
© Georg Thieme Verlag Stuttgart · New York

Copper Triflate: An Efficient Catalyst for Direct Conversion of Secondary Alcohols into Azides

Poonam Khedar
Department of Chemistry, Birla Institute of Technology and Science, Pilani 333031 , India   Fax: +91(1596)244183   Email: anilkumar@pilani.bits-pilani.ac.in
,
Kasiviswanadharaju Pericherla
Department of Chemistry, Birla Institute of Technology and Science, Pilani 333031 , India   Fax: +91(1596)244183   Email: anilkumar@pilani.bits-pilani.ac.in
,
Anil Kumar*
Department of Chemistry, Birla Institute of Technology and Science, Pilani 333031 , India   Fax: +91(1596)244183   Email: anilkumar@pilani.bits-pilani.ac.in
› Author Affiliations
Further Information

Publication History

Received: 22 October 2013

Accepted after revision: 09 December 2013

Publication Date:
16 January 2014 (online)


Abstract

A simple, practical, and efficient strategy has been demonstrated for the direct synthesis of organic azides from alcohols using azidotrimethylsilane (TMSN3) as azide source in the presence of copper(II) triflate [Cu(OTf)2]. A variety of alcohols was converted into the corresponding azides in good to excellent yields. The formation of an intermediate carbocation was confirmed by the synthesis of bis(diphenylmethyl) ether.

Supporting Information

 
  • References

  • 1 Mazal C, Jonas J, Žák Z. Tetrahedron 2002; 58: 2729
  • 2 Gardiner M, Grigg R, Kordes M, Sridharan V, Vicker N. Tetrahedron 2001; 57: 7729
  • 3 Salunkhe AM, Ramachandran PV, Brown HC. Tetrahedron Lett. 1999; 40: 1433
  • 4 Bräse S, Gil C, Knepper K, Zimmermann V. Angew. Chem. Int. Ed. 2005; 44: 5188
  • 5 Kohn M, Breinbauer R. Angew. Chem. Int. Ed. 2004; 43: 3106
  • 6 Gololobov YG, Kasukhin LF. Tetrahedron 1992; 48: 1353
  • 7 Radominska A, Drake R. Methods Enzymol. 1994; 230: 330
  • 8 Kunz H. Angew. Chem., Int. Ed. Engl. 1987; 26: 294
  • 9 Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
  • 10 Lutz J.-F. Angew. Chem. Int. Ed. 2007; 46: 1018
  • 11 Liu D, Zheng Y, Steffen W, Wagner M, Butt H.-J, Ikeda T. Macromol. Chem. Phys. 2013; 214: 56
  • 12 Jiang L, Wang Z, Bai S.-Q, Hor TS. A. Dalton Trans. 2013; 42: 9437
  • 13 Lin TS, Mancini WR. J. Med. Chem. 1983; 26: 544
  • 14 Alvarez SG, Alvarez MT. Synthesis 1997; 413
  • 15 Hughes DL. Org. Prep. Proced. Int. 1996; 28: 127
  • 16 Mitsunobu O, Wada M, Sano T. J. Am. Chem. Soc. 1972; 94: 679
  • 17 Lee J, Lee J, Kang M, Shin M, Kim J.-M, Kang S.-U, Lim J.-O, Choi H.-K, Suh Y.-G, Park H.-G, Oh U, Kim H.-D, Park Y.-H, Ha H.-J, Kim Y.-H, Toth A, Wang Y, Tran R, Pearce LV, Lundberg DJ, Blumberg PM. J. Med. Chem. 2003; 46: 3116
  • 18 Iranpoor N, Firouzabadi H, Akhlaghinia B, Nowrouzi N. Tetrahedron Lett. 2004; 45: 3291
  • 19 Saito A, Saito K, Tanaka A, Oritani T. Tetrahedron Lett. 1997; 38: 3955
  • 20 Mizuno M, Shioiri T. Chem. Commun. 1997; 2165
  • 21 Thompson AS, Humphrey GR, DeMarco AM, Mathre DJ, Grabowski EJ. J. J. Org. Chem. 1993; 58: 5886
  • 22 Lal B, Pramanik BN, Manhas MS, Bose AK. Tetrahedron Lett. 1977; 18: 1977
  • 23 Rokhum L, Bez G. J. Chem. Sci. 2012; 124: 687
  • 24 Sampath Kumar HM, Subba Reddy BV, Anjaneyulu S, Yadav JS. Tetrahedron Lett. 1998; 39: 7385
  • 25 Batool A, Sima S. J. Braz. Chem. Soc. 2007; 18: 1311
  • 26 Kitamura M, Koga T, Yano M, Okauchi T. Synlett 2012; 23: 1335
  • 27 Soltani Rad MN, Behrouz S, Khalafi-Nezhad A. Tetrahedron Lett. 2007; 48: 3445
  • 28 Sagar Reddy GV, Rao GV, Subramanyam RV. K, Iyengar DS. Synth. Commun. 2000; 30: 2233
  • 29 Kumar A, Sharma RK, Singh TV, Venugopalan P. Tetrahedron 2013; 69: 10724
  • 30 Sawama Y, Nagata S, Yabe Y, Morita K, Monguchi Y, Sajiki H. Chem. Eur. J. 2012; 18: 16608
  • 31 Barbero M, Bazzi S, Cadamuro S, Dughera S. Eur. J. Org. Chem. 2009; 430