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Synthesis 2010(14): 2355-2360
DOI: 10.1055/s-0029-1218795
DOI: 10.1055/s-0029-1218795
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Novel Preparation of Polymer-Supported Iodobenzene and Its Synthetic Utility as a Recyclable Reagent with m-Chloroperbenzoic Acid
Further Information
Received
4 March 2010
Publication Date:
20 May 2010 (online)
Publication History
Publication Date:
20 May 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201014/lookinside/thumbnails/10.1055-s-0029-1218795-1.jpg)
Abstract
Three novel polymer-supported iodobenzene compounds A0, A6, and A10 were prepared from the reaction of commercially available cross-linked poly(p-chloromethyl)styrene with m-iodobenzylalcohol, 6-(m-iodobenzyloxy)-1-hexanol, and 10-(m-iodobenzyloxy)-1-decanol. Their catalytic reactivity and reusability for the oxidative α-tosyloxylation of ketones and the cyclization of N-methoxy-2-arylethanesulfonamides in the presence of m-chloroperbenzoic acid (mCPBA) were confirmed to provide α-tosyloxyketones and N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides, respectively, in good yields.
Key words
polymer-supported PhI - recycle mCPBA - α-tosyloxyketone - ketone - N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxide - catalyst
-
1a For
reviews, see:
Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; San Diego: 1997. -
1b
Moriarty RM.Vaid RK. Synthesis 1990, 431 -
1c
Stang PJ. Angew. Chem., Int. Ed. Engl. 1992, 31: 274 -
1d
Prakash O.Saini N.Sharma PK. Synlett 1994, 221 -
1e
Kitamura T. J. Synth. Org. Chem. 1995, 53: 893 -
1f
Stang PJ.Zhdankin VV. Chem. Rev. 1996, 96: 1123 -
1g
Umemoto T. Chem. Rev. 1996, 96: 1757 -
1h
Kita Y.Takada T.Tohma H. Pure Appl. Chem. 1996, 68: 627 -
1i
Togo H.Hoshina Y.Nogami G.Yokoyama M. J. Synth. Org. Chem. 1997, 55: 90 -
1j
Varvoglis A. Tetrahedron 1997, 53: 1179 -
1k
Zhdankin VV. Rev. Heteroat. Chem. 1997, 17: 133 -
1l
Muraki T.Togo H.Yokoyama M. Rev. Heteroat. Chem. 1997, 17: 213 -
1m
Kitamura T.Fujiwara Y. Org. Prep. Proced. Int. 1997, 29: 409 -
1n
Varvoglis A.Spyroudis S. Synlett 1998, 221 -
1o
Zhdankin VV.Stang PJ. Tetrahedron 1998, 54: 10927 -
1p
Moriarty RM.Prakash O. Adv. Heterocycl. Chem. 1998, 69: 1 -
1q
Togo H.Katohgi M. Synlett 2001, 565 -
1r
Zhdankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 -
1s
Richardson RD.Wirth T. Angew. Chem. Int. Ed. 2006, 45: 4402 -
1t
Ladziata U.Zhdankin V. Synlett 2007, 527 - For reviews, see:
-
2a
Moriarty RM.Vaid RK.Koser GF. Synlett 1990, 365 -
2b
Koser GF. Aldrichimica Acta 2001, 34: 89 -
2c Papers:
Prakash O.Saini N.Sharma PK. Heterocycles 1994, 38, 409 -
2d
Neilands O.Karele B. J. Org. Chem. USSR 1970, 6: 885 -
2e
Koser GF.Wettach RH.Troup JM.Frenz BA. J. Org. Chem. 1976, 41: 3609 -
2f
Koser GF.Wettach RH. J. Org. Chem. 1977, 42: 1476 -
2g
Koser GF.Wettach RH.Smith CS. J. Org. Chem. 1980, 45: 1543 -
2h
Koser GF.Relenyi AG.Kalos AN.Rebrovic L.Wettach RH.
J. Org. Chem. 1982, 47: 2487 -
2i
Moriarty RM.Penmasta R.Awasthi AK.Epa WR.Prakash I. J. Org. Chem. 1989, 54: 1101 -
2j
Moriarty RM.Vaid RK.Hopkins TE.Vaid BK.Prakash O. Tetrahedron Lett. 1990, 31: 201 -
2k
Tuncay A.Dustman JA.Fisher G.Tuncay CI. Tetrahedron Lett. 1992, 33: 7647 -
2l
Moriarty RM.Vaid BK.Duncan MP.Levy SG.Prakash O.Goyal S. Synthesis 1992, 845 -
2m
Prakash O.Goyal S. Synthesis 1992, 629 -
2n
Prakash O.Rani N.Goyal S. J. Chem. Soc., Perkin Trans. 1 1992, 707 -
2o
Prakash O.Saini N.Sharma PK. Synlett 1994, 221 -
2p
Vrama RS.Kumar D.Liesen PJ. J. Chem. Soc., Perkin Trans. 1 1998, 4093 -
2q
Lee JC.Choi Ju.-H. Synlett 2001, 234 - Monomer reagents:
-
3a
Muraki T.Togo H.Yokoyama M. J. Org. Chem. 1999, 64: 2883 -
3b
Nabana T.Togo H. J. Org. Chem. 2002, 67: 4362 -
3c
Misu Y.Togo H. Org. Biomol. Chem. 2003, 1: 1342 -
3d
Ueno M.Nabana T.Togo H. J. Org. Chem. 2003, 68: 6424 - Polymer reagents:
-
3e
Abe S.Sakuratani K.Togo H. Synlett 2001, 22 -
3f
Abe S.Sakuratani K.Togo H. J. Org. Chem. 2001, 66: 6174 -
3g
Sakuratani K.Togo H. ARKIVOC 2003, (vi): 11 -
3h
Ueno M.Togo H. Synthesis 2004, 2673 - Reviews:
-
4a
Ochiai M.Miyamoto K. Eur. J. Org. Chem. 2008, 4229 -
4b
Dohi T.Kita Y. Chem. Commun. 2009, 2073 -
4c
Uyanik M.Ishihara K. Chem. Commun. 2009, 2086 - Papers:
-
4d
Ochiai M.Takeuchi Y.Katayama T.Sueda T.Miyamoto K. J. Am. Chem. Soc. 2005, 127: 12244 -
4e
Dohi T.Maruyama A.Yoshimura M.Morimoto K.Tohma H.Kita Y. Angew. Chem. Int. Ed. 2005, 44: 6193 -
4f
Li J.Chan PWH.Che C. Org. Lett. 2005, 7: 5801 -
4g
Thottumkara AP.Bowsher MS.Vinod TK. Org. Lett. 2005, 7: 2933 -
4h
Dohi T.Maruyama A.Minamitsuji Y.Takenaga N.Kita Y. Chem. Commun. 2007, 1224 -
4i
Richardson RD.Page TK.Altermann S.Paradine SM.French AN.Wirth T. Synlett 2007, 538 -
4j
Yakura T.Konishi T. Synlett 2007, 765 -
4k
Sheng J.Li X.Tang M.Gao B.Huang G. Synthesis 2007, 1165 -
4l
Chen C.Feng X.Zhang G.Zhao Q.Huang G. Synthesis 2008, 3205 -
4m
Uyanik M.Akakura M.Ishihara K. J. Am. Chem. Soc. 2009, 131: 251 -
4n
Miyamoto K.Sei Y.Yamaguchi K.Ochiai M. J. Am. Chem. Soc. 2009, 131: 1382 -
4o
Ojha LR.Kudugunti S.Maddukuri PP.Kommareddy A.Gunna MR.Dokuparthi P.Gottam HB.Botha KK.Parapati DR.Vinod TK. Synlett 2009, 117 -
4p
Dohi T.Minamitsuji Y.Maruyama A.Hirose S.Kita Y. Org. Lett. 2008, 10: 3559 -
4q
Uyanik M.Fukatsu R.Ishihara K. Org. Lett. 2009, 11: 3470 -
4r
Uyanik M.Yasui T.Ishihara K. Bioorg. Med. Chem. Lett. 2009, 19: 3848 -
4s
Yakura T.Tian Y.Yamauchi Y.Omoto M.Konishi T. Chem. Pharm. Bull. 2009, 57: 252 - 5
Yamamoto Y.Togo H. Synlett 2005, 2486 -
6a
Yamamoto Y.Togo H. Synlett 2006, 798 -
6b
Yamamoto Y.Kawano Y.Toy PH.Togo H. Tetrahedron 2007, 63: 4680 -
6c
Akiike J.Yamamoto Y.Togo H. Synlett 2007, 2168 -
6d
Moroda A.Togo H. Synthesis 2008, 1257 -
6e
Ishiwata Y.Togo H. Tetrahedron Lett. 2009, 50: 5354 - 7
Khanna MS.Grag CP.Kapoor RP. Tetrahedron Lett. 1992, 33: 45