Abstract
An efficient synthesis of N-arylsulfonamides with a variety of aryl bromides, aryl iodides and heteroaryl bromides using KF/Al2O3 as a suitable base, CuI as an inexpensive catalyst and N,N′-dimethylethylenediamine (N,N′-DMEDA) as an effective ligand is described.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Romero D L, Morge R A, Genin M J, Biles C, Busso M, Resnick L, Althaus I W, Reusser F, Thomas R C and Tarpley W G 1993 J. Med. Chem. 36 1505
Hester J B, Gibson J K, Cimini M G, Emmert D E, Locker P K, Perricone S C, Skaletzky L L, Sykes J K and West B E 1991 J. Med. Chem. 34 308
Turner S R, Strohbach J W, Tommasi R A, Aristoff P A, Johnson P D, Skulnick H I, Dolak L A, Seest E P, Tomich P K, Bohanon M J, Horng M M, Lynn J C, Chong K T, Hinshaw R R, Watenpaugh K D, Janakiraman M N and Thaisrivongs S J 1998 J. Med. Chem. 41 3467
Serradeil-Le Gal C, Wagnon J, Garcia C, Lacour C, Guiraudou P, Christophe B, Villanova G, Nisato D and Maffrand J P 1993 J. Clin. Invest. 92 224
Cremlyn R 1996 Organosulfur Chemistry: An Introduction (New York: John Wiley and Sons)
Anderson K K 1979 In Sulfonic acid and their derivatives in comrehensive organic chemistry (eds) D H R Barton, W D Ollis and D N Jones (Oxford: Pergamon Press) vol 3
Massah A R, Azadi D, Aliyan H, Momeni A R, Javaherian Naghash H and Kazemi F 2008 Monatshefte fure chemie 139 233
Coutts I G C and Hamblin M 1975 J. Chem. Soc., Perkin Trans 1 2445
Yin J and Buchwald S L 2002 J. Am. Chem. Soc. 124 6043
He H and Wu Y J 2003 Tetrahedron Lett. 44 3385
Steinhuebel D, Palucki M, Askin D and Dolling U 2004 Tetrahedron Lett. 45 3305
Lam P Y S, Vincent G, Clark C G, Deudon S and Jadhav P K 2001 Tetrahedron Lett. 42 3415
Deng W, Liu L, Zhang C Liu M and Guo Q X 2005 Tetrahedron Lett. 46 7295
Blass B E 2002 Tetrahedron 58 9301
Yamawaki J, Ando T and Hanafusa T 1981 Chem. Lett. 1143
Yadav V K and Kapoor K K 1996 Tetrahedron 52 3659
Alloum B A and Villemin D 1989 Synth. Commun. 19 2567
Kabalka G W, Wang L, Namboodiri V and Pagni R M 2000 Tetrahedron Lett. 41 5151
Kabalka G W, Pagni R M and Hair C M 1999 Org. Lett. 1 1423
Schmittling E A and Sawyer J S 1991 Tetrahdron Lett. 32 7207
Hosseinzadeh R, Tajbakhsh M, Mohadjerani M and Mehdinejad H 2004 Synlett. 1517
Hosseinzadeh R, Tajbakhsh M, Mohadjerani M and Alikarami M 2005 Synlett. 1101
Hosseinzadeh R, Tajbakhsh M and Alikarami M 2006 Tetrahdron Lett. 47 5203
Hosseinzadeh R, Tajbakhsh M and Alikarami M 2006 Synlett 2124
Hosseinzadeh R, Tajbakhsh M, Alikarami M and Mohadjerani M 2008 J. Het. Chem. 45 1815
Hosseinzadeh R, Sarrafi Y, Mohadjerani M and Mohammadpourmir F 2008 Tetrahdron Lett. 49 840
Hosseinzadeh R, Golchoubian H and Masoudi M 2008 J. Chin. Chem. Soc. 55 649
Hosseinzadeh R, Tajbakhsh M, Mohadjerani M Rezaei P and Alikarami M 2008 Synth. Commun. 38 3021
Hosseinzadeh R, Tajbakhsh M, Mohadjerani M and Ghorbani E 2008 Chin. J. Chem. 26 2120
Badr M Z A, Aly M M and Fahmy A M 1981 J. Org. Chem. 46 4784
Hellwinkel D and Supp M 1976 Chem. Ber. 109 3749
Lopez-Alvarado P, Avendano C and Menendez J C 1996 J. Org. Chem. 61 5865
Raiford L Ch and Hazelt S E 1935 J. Am. Chem. Soc. 57 2172
Gribble G W and Bousquet F P 1971 Tetrahedron 27 3785
Sus O, Moller K and Heiss H 1956 Ann. 598 123
Reverdin F 1909 Chem. Ber. 42 1523
Holmes T J and Lawton R G 1983 J. Org. Chem. 48 3146
Saito S, Takeda M, Kugita H and Higaki K 1962 Yakugaku Kenky 34 42
Berbalk H, Eichinger K and Decker E 1976 Monatshefte fure chemie 107 401
Seisaku I, Yasuo T and Mitsuo O 1975 Yuki Gosei Kagaku Kyokaishi 33 190
Raper H S, Thompson J T and Cohen J B 1904 J. Chem. Soc. Trans 85 371
Reverdin F and Crepieux P 1902 Chem. Ber. 35 1439
Klamann D and Fabienke E 1959 Chem. Ber. 92 712
Moustafa S O and Ahmad A R 2003 Phosphorus Sulfur Silicon 178 475
Seisaku I, Shigeto H, Kazuhiro T and Mitsuo O 1978 Nippon Kagaku Kaishi 86
English J, Chappell D and Bell P 1942 J. Am. Chem. Soc. 64 2516
Angyal S J, Morris W O and Warburaton W K 1952 Australian J. Sci. Research A5 368
Chittum J W, Tindall C G, Howells R D, Coates V and Shie M D 1974 J. Chem. Eng. Data 19 294
Reitsema R H and Hunter J H 1949 J. Am. Chem. Soc. 71 1680
Campaigne E and Monroe P A 1954 J. Am. Chem. Soc. 76 2447
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Hosseinzadeh, R., Tajbakhsh, M., Mohadjerani, M. et al. Copper-catalysed N-arylation of arylsulfonamides with aryl bromides and aryl iodides using KF/Al2O3 . J Chem Sci 122, 143–148 (2010). https://doi.org/10.1007/s12039-010-0015-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-010-0015-x