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Synthesis 2009(6): 941-944
DOI: 10.1055/s-0028-1087981
DOI: 10.1055/s-0028-1087981
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A One-Pot Method for the Iodination of Aryl Amines via Stable Aryl Diazonium Silica Sulfates Under Solvent-Free Conditions
Further Information
Received
18 August 2008
Publication Date:
02 March 2009 (online)
Publication History
Publication Date:
02 March 2009 (online)

Abstract
A convenient and rapid one-pot method for the synthesis of iodoarenes is developed which involves the sequential diazotization-iodination of aromatic amines with sodium nitrite, silica sulfuric acid and potassium iodide under solvent-free conditions at room temperature. Various aromatic amines possessing electron-withdrawing groups or electron-donating groups are converted into the corresponding aryl iodides in good yields.
Key words
diazotization-iodination - aromatic amines - iodoarenes - silica sulfuric acid
-
1a
Diederich F.Stang PJ. Metal-Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 1998. -
1b
Kotha S.Lahiri K.Kashinath D. Tetrahedron 2002, 58: 9633 -
1c
Bellina F.Carpita A.Rossi R. Synthesis 2004, 2419 -
1d
Prajapati D.Gohain M. Tetrahedron 2004, 60: 815 -
1e
de Vries JG. Can. J. Chem. 2001, 79: 1086 -
1f
Cacchi S.Fabrizi G.Goggiomani A. Heterocycles 2002, 56: 613 -
2a
Seevers RH.Counsell RE. Chem. Rev. 1982, 82: 575 -
2b
Volkert WA.Hoffman TJ. Chem. Rev. 1999, 99: 2269 - 3
Yu S.-B.Watson AD. Chem. Rev. 1999, 99: 2353 -
4a
Hajipour AR.Arbabian M.Ruoho AE. J. Org. Chem. 2002, 67: 8622 -
4b
Narender N.Srinivasu P.Kulkarni SJ.Raghavan KV. Synth. Commun. 2002, 32: 2319 -
4c
Firouzabadi H.Iranpoor N.Shiri M. Tetrahedron Lett. 2003, 44: 8781 -
4d
Iskra J.Stavber S.Zupan M. Tetrahedron Lett. 2008, 49: 893 -
4e
Stavber S.Jereb M.Zupan M. Synthesis 2008, 1487 -
5a
Olah GA.Wang Q.Sandford G.Prakash GKS. J. Org. Chem. 1993, 58: 3194 -
5b
Lulinski P.Skulski L. Bull. Chem. Soc. Jpn. 1999, 72: 115 -
5c
Chaikovski VK.Kharlova TS.Filimonov VD.Saryucheva TA. Synthesis 1999, 748 -
5d
Kraszkiewicz L.Sosnowski M.Skulski L. Synthesis 2006, 1195 -
5e
Filimonov VD.Semenischeva NI.Krasnokutskaya EA.Hwang HY.Chi KW. Synthesis 2008, 401 -
6a
The Chemistry of Diazonium and Diazo Groups
Patai S. Wiley; New York: 1978. -
6b
Galli C. Chem. Rev. 1988, 88: 765 -
6c
Roglans A.Pla-Quintana A.Moreno-Mañas M. , - 7
Doyle MP.Siegfried B.Dellaria JF. J. Org. Chem. 1977, 42: 2426 -
8a
Friedman L.Chlebowsky JF. J. Org. Chem. 1968, 33: 1636 -
8b
Smith WB.Ho OC. J. Org. Chem. 1990, 55: 2543 - 9
Baik W.Luan W.Lee HJ.Yoon CH.Koo S.Kim BH. Can. J. Chem. 2005, 83: 213 - 10
Krasnokutskaya EA.Semenischeva NI.Filimonov VD.Knochel P. Synthesis 2007, 81 - 11
Gorlushko DA.Filimonov VD.Krasnokutskaya EA.Semenischeva NI.Go BS.Hwang HY.Cha EH.Chi KW. Tetrahedron Lett. 2008, 49: 1080 - 12
Filimonov VD.Semenischeva NI.Krasnokutskaya EA.Tretyakov AN.Hwang HY.Chi KW. Synthesis 2008, 185 -
13a
Zolfigol MA. Tetrahedron 2001, 57: 9509 -
13b
Zolfigol MA.Shirini F.Ghorbani Choghamarani A.Mohammadpoor-Baltork I. Green Chem. 2002, 4: 562 -
13c
Hajipour AR.Mirjalili BBF.Zarei A.Khazdooz L.Ruoho AE. Tetrahedron Lett. 2004, 45: 6607 -
13d
Zolfigol MA.Mirjalili BBF.Bamoniri A.Karimi MA.Zarei A.Khazdooz L.Noei J. Bull. Korean Chem. Soc. 2004, 25: 1414 -
13e
Hajipour AR.Zarei A.Khazdooz L.Mirjalili BBF.Sheikhan N.Zahmatkesh S.Ruoho AE. Synthesis 2005, 3644 -
13f
Hajipour AR.Zarei A.Ruoho AE. Synth. Commun. 2006, 36: 1039 -
13g
Hajipour AR.Zarei A.Khazdooz L.Ruoho AE. Synth. Commun. 2005, 35: 2237 - 14
Dictionary
of Organic Compounds
5th ed.:
Buckingham J. Chapman and Hall; New York: 1982. -
15a
Akelah A.Moet A. Functionalized Polymers and Their Applications Chapman and Hall; London: 1990. -
15b
Hodge P.Sherrington DC. Polymer-supported Reactions in Organic Synthesis John Wiley & Sons; Chichester: 1980. - 16
Clark JH. Catalysis of Organic Reactions by Supported Inorganic Reagents VCH; Weinheim: 1994. - 17
Toda F.Tanaka K. Chem. Rev. 2000, 100: 1025