Abstract
An easy and selective method for monoiodination of phenols using potassium iodide in the presence of benzyltriphenylphosphonium peroxymonosulfate is presented. The reactions have been carried out in acetonitrile to afford the corresponding iodophenols in moderate to high yields.
References
1.
(a)
Fanta P.E.
, Synlett , 1974 , 9 .
2.
Nilsson M.
, Tetrahedron Lett. , 1966 , 679 .
3.
Matsui K.
,
Tobita E.
,
Ando M.
, and
Kondo K.
, Chem. Lett. , 1981 , 1719 .
4.
Suzuki H.
,
Abe H.
, and
Osuka A.
, Chem. Lett. , 1980 , 1363 .
5.
Chaikovski V.K.
,
Kharlova T. S.
,
Filimonov V. D.
, and
Saryucheva T. A.
, Synthesis , 1999 , 748 .
6.
Seevers R.H.
, and
Counsell R. E.
, Chem. Rev. , 1982 , 82 , 575 .
7.
(a)
Merkushev E.B.
, Synthesis , 1988 , 923 .
8.
Boothe R.
,
Dial C.
,
Conaway R.
,
Pagni R. M.
, and
Kabalka G. W.
, Tetrahedron Lett. , 1986 , 22 , 2207 .
9.
Sugita T.
,
Idei M.
,
Ishibashi Y.
, and
Takegami Y.
, Chem. Lett. , 1982 , 1481 .
10.
Umemura S.
,
Onoe A.
, and
Okano M.
Bull. Chem. Soc. Jpn. , 1974 , 47 , 147 .
11.
Radner F.
, J. Org. Chem. , 1988 , 53 , 3548 .
12.
Mukaiyama T.
,
Kitagawa H.
, and
Matsuo J.
, Tetrahedron Lett. , 2000 , 41 , 9383 .
13.
Tour J.M.
, and
Kosynkin D. V.
, Org. Lett. , 2001 , 3 , 991 .
14.
Arsequell G.
,
Espuna G.
,
Valencia G.
,
Barluenga J.
,
Perez Carlon R.
, and
Gonzalez J. M.
Tetrahedron Lett. , 1999 , 40 , 7279 .
15.
Krassowska-Swiebocka B.
,
Lulinski P.
, and
Skulski L.
, Synthesis , 1995 , 926 .
16.
Olah J.A.
,
wang Oi.
,
Sandford G.
, and
Surya Prakash G. K.
, J. Org. Chem. , 1993 , 58 , 3194 .
17.
Dolenc D.
, Synlett , 2000 , 544 .
18.
Rozen S.
, and
Zamir Dov
, J. Org. Chem. , 1990 , 55 , 3552 .
19.
Detty M.R.
,
Nelen M. I.
,
Higgs D. E.
, Org. Lett. , 2001 , 3 , 349 .
20.
For some recent work using Oxone® as an oxidant, see: (a)
Kennedy R.J.
, and
Stock A. M.
, J. Org. Chem. , 1960 , 25 , 1901 .
21.
Hajipour A.R.
, Ind. J. Chem. , 1997 , 36B , 1069 .
22.
Hajipour A.R.
, and
Mahboubkhah N.
, Org. Prep. Proced. Int. , 1999 , 31 , 112 .
23.
Meunier B.
, New J. Chem. , 1992 , 16 , 203 .
24.
(a)
Hajipour A.R.
,
Mallakpour S. E.
, and
Adibi H.
, Chem. Lett. , 2000 , 460 .
25.
Hajipour A.R.
,
Mallakpour S. E.
, and
Adibi H.
, Phosphorus, Sulfur and Silicon , 2000 , 167 , 71 .
26.
Hajipour A.R.
,
Mallakpour S. E.
, and
Adibi H.
, Chem. Lett. , 2001 , 164 .
27.
Hajipour A.R.
,
Mallakpour S. E.
, and
Adibi H.
, Phosphorus, Sulfur and Silicon , 2002 , 177 , 2277 .
28.
Hajipour A.R.
,
Mallakpour S. E.
,
Mohammadpoor-Baltork I.
, and
Adibi H.
, Phosphorus, Sulfur and Silicon , 2000 , 165 , 155 .
29.
Hajipour A.R.
,
Mallakpour S. E.
,
Mohammadpoor-Baltork I.
, and
Adibi H.
, Synth. Commun. , 2001 , 31 , 1625 .
30.
Hajipour A.R.
,
Mallakpour S. E.
,
Mohammadpoor-Baltork I.
, and
Adibi H.
, Phosphorus, Sulfur and Silicon , 2002 , 177 , 2805 .
31.
Hajipour A.R.
,
Mallakpour S. E.
,
Mohammadpoor-Baltork I.
, and
Adibi H.
, Synth. Commun. , 2001 , 31 , 3401 .
32.
Hajipour A.R.
,
Mallakpour S. E.
, and
Adibi H.
, J. Org. Chem. , 2002 , 67 , 8666 .
33.
Hajipour A.R.
,
Mallakpour S. E.
,
Mohammadpoor-Baltork I.
, and
Adibi H.
, Monatsh. Chem. , 2003 , 134 , 45 .
34.
Hajipour A.R.
,
Mallakpour S. E.
,
Mohammadpoor-Baltork I.
, and
Adibi H.
, Molecules , 2002 , 7 , 674 .
35.
Hajipour A.R.
,
Mallakpour S. E.
,
Imanieh H.
, and
Pourmousavi S. A.
, J. Chem. Res. (S) , 2002 , 272 .
36.
Trost B.M.
, and
Braslau R.
, J. Org. Chem. , 1988 , 53 , 532 .
37.Dictionary of Organic Compounds , 6th edn.; Chapman and Hall : London , 1982 .
