Abstract
A convenient and mild one-pot method for the synthesis of iodoarenes
in high yields by the sequential diazotization-iodination
of aromatic amines with a reusable polymeric diazotization agent
in the presence of p -toluenesulfonic
acid at room temperature in water was developed. The method is general
and is the greenest alternative of the known diazotization-iodination
methods. The method is also effective for the preparation of 1H -benzo[d ][1,2,3]triazole
and benzo[d ][1,2,3]thiadiazole.
Key words
diazotization - halogenation - iodination - heterocycles - amines
References
1a </A>
Diederich F.
Stang PJ.
Metal-Catalyzed Cross-Coupling Reactions
Wiley-VCH;
Weinheim:
1998.
1b </A>
Kotha S.
Lahiri K.
Kashinath D.
Tetrahedron
2002,
58:
9633
1c </A>
Bellina F.
Carpita A.
Rossi R.
Synthesis
2004,
2419
1d </A>
Prajapati D.
Gohain M.
Tetrahedron
2004,
60:
815
1e </A>
Tour JM.
J. Org. Chem.
2007,
72:
7477
1f </A>
Ila H.
Baron O.
Wagner AJ.
Knochel P.
Chem. Commun.
2006,
583
1g </A>
Hopf H.
Tetrahedron
2008,
64:
11504
1h </A>
Darses S.
Genet J.-P.
Chem. Rev.
2008,
108:
288
2a </A>
Volkert WA.
Hoffman TJ.
Chem. Rev.
1999,
99:
2269
2b </A>
Yu S.-B.
Watson AD.
Chem. Rev.
1999,
99:
2353
2c </A>
Nilsson M.
Exp.
Clin. Endocrinol. Diabetes
2001,
109:
13
2d </A>
Pleiss U.
J.
Labelled Compd. Radiopharm.
2007,
50:
818
3a </A>
Hanson JR.
J. Chem. Res.
2006,
277
3b </A>
Stavber S.
Jereb M.
Zupan M.
Synthesis
2008,
1487
<A NAME="RZ36811SS-4">4 </A>
Zollinger H.
Diazo Chemistry I: Aromatic and Heteroaromatic
Compounds
VCH;
Weinheim:
1994.
<A NAME="RZ36811SS-5">5 </A>
Tundo P.
Loris A.
Selva M.
Green
Chem.
2007,
9:
777
<A NAME="RZ36811SS-6">6 </A>
Zarei A.
Hajipour AR.
Khazdooz L.
Synthesis
2009,
941
7a </A>
Filimonov VD.
Semenischeva NI.
Krasnokutskaya EA.
Tretyakov AN.
Hwang HY.
Chi K.-W.
Synthesis
2008,
185
7b </A>
Krasnokutskaya EA.
Semenischeva NI.
Filimonov VD.
Knochel P.
Synthesis
2007,
81
7c </A>
Gorlushko DA.
Filimonov VD.
Krasnokutskaya EA.
Semenischeva NI.
Go BS.
Hwang HY.
Cha EH.
Chi K.-W.
Tetrahedron
Lett.
2008,
49:
1080,
7d </A>
Gorlushko DA.
Filimonov VD.
Semenishcheva NI.
Krasnokutskaya EA.
Tret’yakov AN.
Chi K.-W.
Russ. J. Org. Chem.
2008,
44:
1243
7e </A>
Lee YM.
Moon ME.
Vajpayee V.
Filimonov VD.
Chi K.-W.
Tetrahedron
2010,
66:
7418
7f </A>
Moon ME.
Choi Y.
Lee YM.
Vajpayee V.
Trusova M.
Filimonov VD.
Chi K.-W.
Tetrahedron Lett.
2010,
51:
6769
<A NAME="RZ36811SS-8">8 </A>
Filimonov VD.
Trusova ME.
Postnikov PS.
Krasnokutskaya EA.
Lee YM.
Hwang HY.
Kim H.
Chi K.-W.
Org.
Lett.
2008,
10:
3961
9a </A>
Caldarelli M.
Baxendale IR.
Ley SV.
Green Chem.
2000,
2:
43
9b </A>
Merrington J.
James M.
Bradley M.
Chem.
Commun.
2002,
140
10 </A>
For several examples, the resulting
diazonium tosylates can be partially isolated from the aqueous solution
by extraction with ethyl acetate, followed by pouring the organic
solution in diethyl ether. Properties and spectral data of these
salts were identical to those previously obtained by diazotization in
acetic acid.8
<A NAME="RZ36811SS-11">11 </A>
Vogel’s Textbook of Practical Organic Chemistry
5th
ed.:
Furniss B. S.
Hannaford A. J.
Smith P. W. G.
Tatchell A. R.
Longman;
London:
1989.
<A NAME="RZ36811SS-12">12 </A>
Kryska A.
Skulski L.
J. Chem. Res., Synop.
1999,
590
13a </A>
Damschroder RE.
Peterson WD.
Org. Synth.
1955,
3:
106
13b </A>
Hünig S.
Fleckenstein E.
Liebigs
Ann. Chem.
1970,
738:
192
<A NAME="RZ36811SS-14">14 </A>
Aldrich
Handbook of Fine Chemicals and Laboratory Equipment
Aldrich;
Milwaukee:
2006-2007.
<A NAME="RZ36811SS-15">15 </A>
Zielinska A.
Skulski L.
Molecules
2005,
10:
1307
<A NAME="RZ36811SS-16">16 </A>
Barbero M.
Degani I.
Diulgheroff N.
Dughera S.
Fochi R.
Synthesis
2001,
2180
<A NAME="RZ36811SS-17">17 </A>
Yu B.-C.
Shirai Y.
Tour JM.
Tetrahedron
2006,
62:
10303
