RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2005(16): 2486-2488
DOI: 10.1055/s-2005-872697
DOI: 10.1055/s-2005-872697
LETTER
© Georg Thieme Verlag Stuttgart · New York
Facile One-Pot Preparation of [Hydroxy(sulfonyloxy)iodo]arenes from Iodoarenes with MCPBA in the Presence of Sulfonic Acids
Weitere Informationen
Received
7 July 2005
Publikationsdatum:
21. September 2005 (online)
Publikationsverlauf
Publikationsdatum:
21. September 2005 (online)

Abstract
Various [hydroxy(sulfonyloxy)iodo]arenes were simply and efficiently obtained in high yields from the reaction of iodoarenes and MCPBA in the presence of sulfonic acids in a small amount of chloroform at room temperature, through a one-pot procedure.
Key words
Koser’s reagent - [hydroxy(sulfonyloxy)iodo]arene - MCPBA - sulfonic acid - iodoarene - one-pot preparation
- 1
Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; San Diego: 1997. - Reviews:
-
2a
Ochiai M. Rev. Heteroat. Chem. 1989, 2: 92 -
2b
Moriarty RM.Vaid RK. Synthesis 1990, 431 -
2c
Stang PJ. Angew. Chem., Int. Ed. Engl. 1992, 31: 274 -
2d
Prakash O.Saini N.Sharma PK. Synlett 1994, 221 -
2e
Kitamura T. Yuki Gosei Kagaku Kyokaishi 1995, 53: 893 -
2f
Stang PJ.Zhdankin VV. Chem. Rev. 1996, 96: 1123 -
2g
Umemoto T. Chem. Rev. 1996, 96: 1757 -
2h
Kita Y.Takada T.Tohma H. Pure Appl. Chem. 1996, 68: 627 -
2i
Togo H.Hoshina Y.Nogami G.Yokoyama M. Yuki Gosei Kagaku Kyokaishi 1997, 55: 90 -
2j
Varvoglis A. Tetrahedron 1997, 53: 1179 -
2k
Zhdankin VV. Rev. Heteroat. Chem. 1997, 17: 133 -
2l
Muraki T.Togo H.Yokoyama M. Rev. Heteroat. Chem. 1997, 17: 213 -
2m
Kitamura T.Fujiwara Y. Org. Prep. Proced. Int. 1997, 29: 409 -
2n
Varvoglis A.Spyroudis S. Synlett 1998, 221 -
2o
Zhdankin VV.Stang PJ. Tetrahedron 1998, 54: 10927 -
2p
Moriarty RM.Prakash O. Adv. Heterocycl. Chem. 1998, 69: 1 -
2q
Togo H.Katohgi M. Synlett 2001, 565 -
2r
Zhdankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 - Reviews:
-
3a
Moriarty RM.Vaid RK.Koser GF. Synlett 1990, 365 -
3b
Koser GF. Aldrichimica 2001, 34: 89 -
3c
Prakash O.Saini N.Sharma PK. Heterocycles 1994, 38: 409 - Papers:
-
3d
Neilands O.Karele B. J. Org. Chem. USSR (Engl. Transl.) 1970, 6: 885 -
3e
Koser GF.Wettach RH.Troup JM.Bertram AF. J. Org. Chem. 1976, 41: 3609 -
3f
Koser GF.Wettach RH. J. Org. Chem. 1977, 42: 1476 -
3g
Koser GF.Wettach RH.Smith CS. J. Org. Chem. 1980, 45: 1543 -
3h
Koser GF.Relenyi AG.Kalos AN.Rebrovic L.Wettach RH. J. Org. Chem. 1982, 47: 2487 -
3i
Moriarty RM.Penmasta R.Awasthi AK.Epa WR.Prakash I. J. Org. Chem. 1989, 54: 1101 -
3j
Moriarty RM.Vaid RK.Hopkins TE.Vaid BK.Prakash O. Tetrahedron Lett. 1990, 31: 201 -
3k
Tuncay A.Dustman JA.Fisher G.Tuncay CI. Tetrahedron Lett. 1992, 33: 7647 -
3l
Moriarty RM.Vaid BK.Duncan MP.Levy SG.Prakash O.Goyal S. Synthesis 1992, 845 -
3m
Prakash O.Goyal S. Synthesis 1992, 629 -
3n
Prakash O.Rani N.Goyal S. J. Chem. Soc., Perkin Trans. 1 1992, 707 -
3o
Prakash O.Saini N.Sharma PK. Synlett 1994, 221 -
3p
Vrama RS.Kumar D.Liesen PJ. J. Chem. Soc., Perkin Trans. 1 1998, 4093 -
3q
Lee JC.Choi Ju.-H. Synlett 2001, 234 - Monomer reagents:
-
4a
Muraki T.Togo H.Yokoyama M. J. Org. Chem. 1999, 64: 2883 -
4b
Nabana T.Togo H. J. Org. Chem. 2002, 67: 4362 -
4c
Misu Y.Togo H. Org. Biomol. Chem. 2003, 1342 -
4d
Ueno M.Nabana T.Togo H. J. Org. Chem. 2003, 68: 6424 - Polymer reagents:
-
4e
Abe S.Sakuratani K.Togo H. Synlett 2001, 22 -
4f
Abe S.Sakuratani K.Togo H. J. Org. Chem. 2001, 66: 6174 -
4g
Ueno M.Togo H. Synthesis 2004, 2673 -
5a
Tohma H.Maruyama A.Maeda A.Maegawa T.Dohi T.Shiro M.Morita T.Kita Y. Angew. Chem. Int. Ed. 2004, 43: 3595 -
5b
Dohi T.Maruyama A.Yoshimura M.Morimoto K.Tohma H.Shiro M.Kita Y. Chem. Commun. 2005, 2205 -
6a
Sharefkin JG.Saltzman H. Org. Synth., Coll. Vol. V Wiley; New York: 1973. p.660 -
6b
McKillop A.Kemp D. Tetrahedron 1989, 45: 3299 - 7
Lee JC.Choi JH.Lee YC. Synlett 2001, 1563 - 8
Stang PJ.Surber BW.Chen Z.Roberts KA.Anderson AG. J. Am. Chem. Soc. 1987, 109: 228 - 9
Hatzigrioriou E.Varvoglis A.Christianopoulou MB. J. Org. Chem. 1990, 55: 315 - 10
Paputsi I.Spyroudis S.Varvoglis A.Raptopulou CP. Tetrahedron 1997, 53: 6097 - 11
Carman CS.Koser G. J. Org. Chem. 1983, 48: 2534 - 12
Zhdankin VV.Kuehl CJ.Krasutsky AP.Boltz JT.Simonsen AJ. J. Org. Chem. 1996, 61: 6547