Synlett 2012; 23(10): 1554-1555
DOI: 10.1055/s-0031-1290687
spotlight
© Georg Thieme Verlag Stuttgart · New York

Azidotrimethylsilane

Bao-Le Li
The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050024, P. R. of China, Email: [email protected]
› Author Affiliations
Further Information

Publication History

Publication Date:
29 May 2012 (online)

Introduction

Azidotrimethylsilane (TMSN3) is a clear, colorless, quite stable organosilane reagent and decomposes slowly even at 200 °C. It is considered a very convenient and safer replacement for hydrazoic acid as an azide source in many reactions.[ 1 ] It has been used for the synthesis of aryl 1,2,3-triazoles,[2] [3] [4] [5] tetrazoles,[ 6,7 ] functionalized bicyclic triazoles,[ 8 ] azides,[9] [10] [11] [12] [13] [14] [15] and N-tetrazolated diamine derivative.[ 16 ] In addition, azidotrimethylsilane has been employed for the preparation of proline-derived chiral aminotriazole ligands.[ 17 ] It was found to be a useful reagent for the aziridine ring opening to obtain azidomethyl-substituted pyrrole precursors,[ 18 ] or kinetic resolution of monosubstituted epoxide for the synthesis of optically pure 1-azido-2-trimethylsiloxyalkanes.[ 19 ]

Azidotrimethylsilane can be conveniently and rapidly prepared by adding chlorotrimethylsilane dropwise to a stirred solution of NaN3 in diethylene glycol dimethyl ether.[ 1 ]

Zoom Image
Scheme 1
 
  • References

  • 1 Birkofer L, Wegner P. Org. Syn. 1970; 50: 107
  • 2 Stazi F, Cancogni D, Turco L, Westerduin P, Bacchi S. Tetrahedron Lett. 2010; 51: 5385
  • 3 Fukuzawa SI, Shimizu E, Kikuchi S. Synlett 2007; 2436
  • 4 Majumdar KC, Ray K. Synthesis 2011; 3767
  • 5 Smith AG, Johnson JS. Org. Lett. 2010; 12: 1809
  • 6 Kennedy LJ. Tetrahedron Lett. 2010; 51: 2010
  • 7 Kumar MR, Park K, Lee S. Adv. Synth. Catal. 2010; 352: 3255
  • 8 Kim MS, Yoon HJ, Lee BK, Kwon JH, Lee WK, Kim Y, Ha HJ. Synlett 2005; 2187
  • 9 Zapico JM, Serra P, García-Sanmartín J, Filipiak K, Carbajo RJ, Schott AK, Pineda-Lucena A, Martínez A, Martín-Santamaría S, Pascual-Teresa B, Ramos A. Org. Biomol. Chem. 2011; 9: 4587
  • 10 Chan LY, Kim S, Chung WT, Long C, Kim S. Synlett 2011; 415
  • 11 Montagu A, Roy V, Balzarini J, Snoeck R, Andrei G, Agrofoglio LA. Eur. J. Med. Chem. 2011; 46: 778
  • 12 Shetti VS, Ravikanth M. Eur. J. Org. Chem. 2010; 494
  • 13 Tsai C.-S, Liu P.-Y, Yen H.-Y, Hsua T.-L, Wong C.-H. Chem. Commun. 2011; 46: 5575
  • 14 Smith AG, Johnson JS. Org. Lett. 2010; 12: 1784
  • 15 Hu HG, Wang SZ, Zhang CM, Wang L, Ding L, Zhang JP, Wu Q. Bioorg. Med. Chem. Lett. 2010; 20: 7537
  • 16 Athanassopoulos CM, Garnelis T, Magoulas G, Papaioannou D. Synthesis 2006; 3134
  • 17 Cambeiro XC, Pericãs MA. Adv. Synth. Catal. 2011; 353: 113
  • 18 Kim JH, Lee SB, Lee WK, Yoon DH, Ha HJ. Tetrahedron 2011; 67: 3553
  • 19 Larrow JF, Schaus SE, Jacobsen EN. J. Am. Chem. Soc. 1996; 118: 7420
  • 20 Augustine JK, Bombrun A, Mandal AB, Alagarsamy P, Atta RN, Selvam P. Synthesis 2011; 1477
  • 21 Sukhorokov AY, Bliznets IV, Lesiv AV, Khomutova YA, Strelenko YA. Synthesis 2005; 1077
  • 22 Lee BK, Kim MS, Hahm HS, Kim DS, Lee WK, Ha HG. Tetrahedron 2006; 62: 8393
  • 23 Jiang ZP, Xiao Z, Zhang GH, Gan LB, Wang D, Zhang WX. Tetrahedron Lett. 2010; 51: 415
  • 24 Chen F, Qin C, Cui YX, Jiao N. Angew. Chem. Int. Ed. 2011; 50: 11487
  • 25 Barange DK, Tu YC, Kavala V, Kuo CW, Yao CF. Adv. Synth. Catal. 2010; 353: 41
  • 26 Pal AP. J, Mallick A, Reddy YS, Vankar YD. Tetrahedron Lett. 2010; 51: 6334
  • 27 Sarkar SD, Studer A. Org. Lett. 2010; 12: 1992