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Synthesis 2013; 45(19): 2706-2710
DOI: 10.1055/s-0033-1339648
DOI: 10.1055/s-0033-1339648
paper
A Simple and Effective Synthesis of Aryl Azides via Arenediazonium Tosylates
Weitere Informationen
Publikationsverlauf
Received: 22. Mai 2013
Accepted after revision: 30. Juli 2013
Publikationsdatum:
14. August 2013 (online)
Abstract
Aromatic azides are formed in high yield from arenediazonium tosylates and sodium azide in water at room temperature or from aromatic amines via diazotization in the presence of p-TsOH. Besides being experimentally simple, these methods do not require any metal catalysis and provide clean products without purification.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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References
- 1a Scriven EF. V, Turnbull K. Chem. Rev. 1988; 88: 297
- 1b Bräse S, Gil C, Knepper K, Zimmermann V. Angew. Chem. Int. Ed. 2005; 44: 5188
- 1c Bräse S, Banert K. Organic Azides . Wiley; Wiltshire: 2010
- 1d Chiba S. Synlett 2012; 23: 21
- 2a Gololobov YG, Kazukhin LF. Tetrahedron 1992; 48: 1353
- 2b Köhn M, Breinbauer R. Angew. Chem. Int. Ed. 2004; 43: 3106
- 2c Saxon E, Bertozzi CR. Science 2007; 287: 2007
- 2d Schilling CI, Jung N, Biskup M, Schepers U, Braese S. Chem. Soc. Rev. 2011; 40: 4840
- 2e Vallee MR, Majkut P, Wilkening I, Weise C, Muller G, Hackenberger CP. Org. Lett. 2011; 13: 5440
- 3 Gritsan NP, Platz MS, Borden WT. The Study of Nitrenes by Theoretical Methods . In Theoretical Methods in Photochemistry . Kutateladze A. Taylor and Francis; Boca Raton: 2005: 235-356
- 4 Robinette D, Neomati N, Tomer KB, Borchers CH. Expert Rev. Proteomics 2006; 3: 399
- 5a Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed. 2002; 41: 2596
- 5b Himo F, Demko ZP, Noodleman L, Sharpless KB. J. Am. Chem. Soc. 2003; 125: 9983
- 5c Zhang L, Chen X, Xue P, Sun HH, Williams ID, Sharpless KB, Fokin VV, Jia G. J. Am. Chem. Soc. 2005; 127: 15998
- 5d Bock VD, Hiemstra H, van Maarseveen JH. Eur. J. Org. Chem. 2006; 51
- 5e Moorhouse AD, Santos AM, Gunaratnam M, Moore M, Neidle S, Moses JE. J. Am. Chem. Soc. 2006; 128: 15972
- 5f Meldal M, Tornoe CW. Chem. Rev. 2008; 108: 2952
- 5g Wang Y, Lin Q. Org. Lett. 2009; 11: 3570
- 5h Ngai MH, Yang P.-Y, Liu K, Shen Y, Wenk MR, Yao SQ, Lear MJ. Chem. Commun. 2010; 44: 8335
- 5i Kwok SW, Fotsing JR, Fraser RJ, Rodionov VO, Fokin VV. Org. Lett. 2010; 12: 4217
- 5j Lee K, Campbell J, Swoboda JG, Cuny GD, Walker S. Bioorg. Med. Chem. Lett. 2010; 20: 1767
- 5k Wilkening I, del Signore G, Hackenberger CP. R. Chem. Commun. 2011; 47: 349
- 5l Agalave SG, Maujan SR, Pore VS. Chem. Asian J. 2011; 6: 2696
- 6 Salic A, Mitchison TJ. Proc. Natl. Acad. Sci. U. S. A. 2008; 105: 2415
- 7 Azagarsamy MA, Anseth KS. ACS MacroLett. 2013; 2: 5
- 8a Holzinger M, Vostrowsky O, Hirsh A, Hennrich F, Kappes M, Weiss R, Jellen F. Angew. Chem. Int. Ed. 2001; 40: 4002
- 8b Liu LH, Yan MD. Nano Lett. 2009; 9: 3375
- 8c Tanaka M, Sawaguchi T, Sato Y, Yoshioka K, Niwa O. Langmuir 2011; 27: 170
- 8d Evans RA. Aust. J. Chem. 2007; 60: 384
- 9a Liu Q, Tor Y. Org. Lett. 2003; 5: 2571
- 9b Goddard-Borger ED, Stick RV. Org. Lett. 2007; 9: 3797
- 9c Kitamura M, Yano M, Tashiro N, Miyagawa S, Sando M, Okauchi T. Eur. J. Org. Chem. 2011; 458
- 10a Tao C.-Z, Cui X, Li J, Liu A.-X, Liu L, Liu Q.-X. Tetrahedron Lett. 2007; 48: 3525
- 10b Li Y, Gao L.-X, Han F.-S. Chem. Eur. J. 2010; 16: 7969
- 10c Grimes KD, Gupte A, Aldrich CC. Synthesis 2010; 1441
- 11 Telvekar VN, Sasane KA. Synth. Commun. 2012; 42: 1085
- 12a Zarei A, Hajipour AR, Khazdooz L, Aghaei H. Tetrahedron Lett. 2009; 50: 4443
- 12b Zarchi MA. K, Nabei R. J. Appl. Polym. Sci. 2012; 124: 2362
- 13 Smith CJ, Smith CD, Nikbin N, Ley SV, Baxendale IR. Org. Biomol. Chem. 2011; 9: 1927
- 14 Bretherick’s Handbook of Reactive Chemical Hazards . 6th ed., Vol. 2. Urben P. Butterworth-Heinemann; Oxford: 1999: 99-100
- 15 Patro B, Merrett MC, Makin SD, Murphy JA, Parkes KE. B. Tetrahedron Lett. 2000; 41: 421
- 16 Filimonov VD, Trusova ME, Krasnokutskaya EA, Postnikov PS, Lee YM, Hwang HY, Kim H, Chi K.-W. Org. Lett. 2008; 10: 3961
- 17 Tretyakov AN, Krasnokutskaya EA, Gorlushko DA, Ogorodnikov VD, Filimonov VD. Tetrahedron Lett. 2011; 52: 85
- 18 Stacy DM, Le Quement ST, Hansen CL, Clausen JW, Tolker-Nielson T, Brummond JW, Giskov M, Nielsen TE, Blackwell HE. Org. Biomol. Chem. 2013; 11: 938
- 19 Ueno M, Hori C, Suzawa K, Ebisawa M, Kondo Y. Eur. J. Org. Chem. 2005; 1965
- 20 Bencivenni G, Cesari R, Nanni D, El Mkami H, Walton JC. Org. Biomol. Chem. 2010; 8: 5097
- 21 Paek S, Baik C, Ko J, Kang M.-s, Kang H. J. Organomet. Chem. 2010; 695: 821
- 22 Hahn FE, Langenhahn V, Meier N, Luegger T, Fehlhammer WP. Chem. Eur. J. 2003; 9: 704
- 23 Smith AB, Sugasawa K, Atasoylu O, Yang C.-PH, Horwitz SB. J. Med. Chem. 2011; 54: 6319
- 24 Griffits J, McDarmaid RI. J. Soc. Dyers Colour. 1978; 94: 65
- 25 Thomas JR, Liu X, Hergenrother PJ. J. Am. Chem. Soc. 2005; 127: 12434
- 26 Guggenheim KG, Toru H, Kurth MJ. Org. Lett. 2012; 14: 3732
- 27 Liu C.-Y, Knochel P. J. Org. Chem. 2007; 72: 7106
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