Abstract
A new room-temperature ionic liquid (RTIL) supported [hydroxy(tosyloxy)iodo]benzene (ion-supported HTIB) reagent was synthesised by three kinds of effective methods in high yields, which combined the advantages of ionic liquids and the hypervalent iodine. Ion-supported HTIB was an effective reagent for one-step conversion of ketones to the corresponding α-tosyloxylated ketones in the ionic liquid [emim]BF4or acetonitrile under microwave. After the conversion reaction, the reagent was transformed into ion-supported iodobenzene, which could be recovered and regenerated easily without lost of activity.
References
1.
Varma R.S.
, and
Kumar D.
, Catal. Lett. , 1998 , 53 , 225 .
2.
Varma R.S.
,
Naicker K. P.
, and
Kumar D.
, J. Mol. Catal. A Chem. , 1999 , 149 , 153 .
3.
Hou R.S.
,
Wang H. M.
,
Tsai H. H.
, and
Chen L. C.
, J. Chin. Chem. Soc. , 2006 , 53 , 863 .
4.
Aggarwal R.
, and
Sumran G.
, Synth. Commun. , 2006 , 36 , 875 .
5.
Hou R.S.
,
Wang H. M.
,
Huang H. Y.
, and
Chen L. C.
, J. Chin. Chem. Soc. , 2004 , 51 , 1417 .
6.
Varma R.S.
,
Kumar D.
, and
Liesen P. J.
, J. Chem. Soc., Perkin Trans. 1 , 1998 , 24 , 4093 .
7.
Xie Y.Y.
,
Chen Z. C.
, and
Zheng Q. G.
, Synthesis. , 2002 , 1505 .
8.
Li M.
,
Zhao G. L.
,
Wen L. R.
,
Cao W.
,
Zhang S. S.
, and
Yang H. Z.
, J. Heterocycl. Chem. , 2005 , 42 , 209 .
9.
Li M.
,
Zhao G. L.
,
Wen L. R.
, and
Yang H. Z.
, Synth. Commun. , 2005 , 35 , 493 .
10.
Creary X.
, and
Geiger C. C.
, J. Am. Chem. Soc. , 1982 , 104 , 4151 .
11.
Creary X.
, and
Rollin A. J.
, J. Org. Chem. , 1977 , 42 , 4226 .
12.
House H.O.
, and
Berkowitz W. F.
, J. Org. Chem. , 1963 , 28 , 307 .
13.
Charlton J.L.
,
Lai H. K.
, and
Lypka G. N.
, Can. J. Chem. , 1980 , 58 , 458 .
14.
Wilson R.M.
, and
Sheehan J. C.
, J. Am. Chem. Soc. , 1969 , 91 , 7378 .
15.
Khanna S.M.
,
Garg C. P.
, and
Kapoor R. R.
, Tetrahedron Lett. , 1992 , 33 , 1495 .
16.
Yamamoto Y.
, and
Togo H.
, Synlett. , 2006 , 798 .
17.
Akiike J.
,
Yamamoto Y.
, and
Togo H.
, Synlett , 2007 , 2168 .
18.
Yamamoto Y.
,
Kawano Y.
,
Toy P. H.
, and
Togo H.
, Tetrahedron , 2007 , 63 , 4680 .
19.
Abe S.
,
Sakuratani K.
, and
Togo H.
, J. Org. Chem. , 2001 , 66 . 6174 .
20.
Nabana T.
, and
Togo H.
, J. Org. Chem. , 2002 , 67 , 4362 .
21.
Ueno M.
,
Nabana T.
, and
Togo H.
, J. Org. Chem. , 2003 , 68 , 6424 .
22.
Kumar D.
,
Sundaree M. S.
,
Patel G.
,
Rao V. S.
, and
Varma R. S.
, Tetrahedron Lett. , 2006 , 47 , 8239 .
23.
Kumar S.
,
Kumar A.
,
Gupta R. K.
, and
Kumar D.
, Synth. Commun. , 2008 , 38 , 338 –345 .
24.
Lidström P.
,
Tierney J.
,
Wathey B.
, and
Westman J.
, Tetrahedron , 2001 , 57 , 9225 .
25.
Welton T.
, Chem. Rev. , 1999 , 99 , 2071 .
26.
Wasserscheid P.
, and
Keim W.
, Angew. Chem., Int. Ed. , 2000 , 39 , 3772 .
27.
Dupont J.
,
de Souza R. F.
, and
Suarez P. A. Z.
, Chem. Rev. , 2002 , 102 , 3667 .
28.
Hakkou H.
,
Eynde J. J. V.
,
Hamelin J.
, and
Bazureau J. P.
, Tetrahedron , 2004 , 60 , 3745 .
29.
Hakkou H.
,
Vanden Eynde J. J.
,
Hamelin J.
, and
Bazureau J. P.
, Synthesis , 2004 , 1793 .
30.
Fraga-Dubreuil J.
, and
Bazureau J. P.
, Tetrahedron , 2003 , 59 , 6121 .
31.
Fraga-Dubreuil J.
, and
Bazureau J. P.
, Tetrahedron Lett , 2001 , 42 , 6097 .
32.
Handy S.T.
, and
Okello M.
, Tetrahedron Lett , 2003 , 44 , 8399 .
33.
Qian W.X.
,
Jin E. L.
,
Bao W. L.
, and
Zhang Y. M.
, Angew. Chem. Int. Ed. , 2005 , 44 , 952 .
34.
Koser G.F.
,
Relenyi A. G.
,
Kalos A. N.
,
Rebrovic L.
, and
Wettach R. H.
, J. Org. Chem. , 1982 , 47 , 2487 .
35.
Jong C.L.
, and
Ju-Hee C.
, Synlett. , 2001 , 234 .
36.
John D.R. S.
,
Killeen N. M.
,
Knowles D. A.
,
Yau S. C.
,
Bagley M. C.
, and
Tomkinson N.C.O
, Org. Lett , 2007 , 48 , 4009 .
