Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2008(18): 2885-2887
DOI: 10.1055/s-0028-1083600
DOI: 10.1055/s-0028-1083600
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Convenient One-Pot Synthesis of Sulfonyl Azides from Sulfonic Acids
Further Information
Received
7 August 2008
Publication Date:
23 October 2008 (online)
Publication History
Publication Date:
23 October 2008 (online)
![](https://www.thieme-connect.de/media/synlett/200818/lookinside/thumbnails/10.1055-s-0028-1083600-1.jpg)
Abstract
We have developed a one-pot process for preparing sulfonyl azides by treating sulfonic acids with trichloroacetonitrile, triphenylphosphine, and sodium azide at room temperature. A wide range of sulfonyl azides was synthesized in excellent yields under mild conditions.
Key words
sulfonic acid - sulfonyl azide - trichloroacetonitrile - triphenylphosphine - sodium azide
-
1-1a
Goddard-Borger ED.Stick RV. Org. Lett. 2007, 9: 3797 -
1-1b
Harned AM.Sherrill WM.Flynn DL.Hanson PR. Tetrahedron 2005, 61: 12093 -
1-1c
Charette AB.Wurz RP.Ollevier T. J. Org. Chem. 2000, 65: 9252 -
1-1d
Taber DF.Ruckle RE.Hennessy MJ. J. Org. Chem. 1986, 51: 4077 - 1-2
Waser J.Nambu H.Carreira EM. J. Am. Chem. Soc. 2005, 127: 8294 -
1-3a
Ruppel JV.Jones JE.Huff CA.Kamble RM.Chen Y.Zhang XP. Org. Lett. 2008, 10: 1995 -
1-3b
Waser J.Gaspar B.Nambu H.Carreira EM. J. Am. Chem. Soc. 2006, 128: 11693 -
1-4a
Masterson DS.Shckleford JP. Synlett 2007, 1302 -
1-4b
Panchaud P.Chabaud L.Landais Y.Ollivier C.Renaud P.Zigmantas S. Chem. Eur. J. 2004, 10: 3606 -
1-5a
Cho SH.Chang S. Angew. Chem. Int. Ed. 2008, 47: 2836 -
1-5b
Kim JY.Kim SH.Chang S. Tetrahedron Lett. 2008, 49: 1745 -
1-5c
Han Y.Xie Y.-X.Zhao L.-B.Fan M.-J.Liang Y.-M. Synthesis 2008, 87 -
1-5d
Ruppel JV.Kamble RM.Zhang XP. Org. Lett. 2007, 9: 4889 -
1-6a
El-Sayed RA. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179: 237 -
1-6b
Andersen NG.Ramsden PD.Che D.Parvez M.Keay BA. Org. Lett. 1999, 1: 2009 -
1-6c
Harmon RE.Wellman G.Gupta SK. J. Org. Chem. 1973, 38: 11 -
1-6d
Leffler JE.Tsuno Y. J. Org. Chem. 1963, 28: 902 - 1-7
Humlian J.Gobec S. Tetrahedron Lett. 2005, 46: 4069 - 1-8
Fujita S. Synthesis 1982, 423 -
1-9a
Barco A.Benetti S.Pollini P.Tadia R. Synthesis 1974, 877 -
1-9b
Frankel M.Moses P. Tetrahedron 1960, 9: 289 - 1-10
Reynolds RC.Crooks PA.Maddry JA.Akhtar MS.Montgomery JA.Secrist JA. J. Org. Chem. 1992, 57: 2983 - 1-11
Blotny G. Tetrahedron Lett. 2003, 44: 1499 - 1-12
Laurent N.Lafont D.Boullanger P.Mallet JM. Carbohydr. Res. 2005, 340: 1885 - 1-13
Farng L.-PO.Kice JL. J. Am. Chem. Soc. 1981, 103: 1137 - 1-14
Katritzky A.Widyan K.Gyanda K. Synthesis 2008, 1201 -
1-15a
Chantarasriwong O.Jang DO.Chavasiri W. Tetrahedron Lett. 2006, 47: 7489 -
1-15b
Jang DO.Cho DH.Kim J.-G. Synth. Commun. 2003, 33: 2885 -
1-15c
Kim J.Jang DO. Synth. Commun. 2001, 31: 395 -
1-15d
Jang DO.Park DJ.Kim J. Tetrahedron Lett. 1999, 40: 5323