Abstract
Polymer-supported hypervalent iodine reagents, bearing (diacetoxy)iodo,
(dihalo)iodo, (hydroxy)(tosyloxy)iodo, (hydroxy)(phosphoryloxy)iodo,
aryliodonium, 1,2-benziodoxol-3-one, and hypervalent iodine groups
as counter anions, can be used for various oxidative functional
group conversions of substrates. These polymer species can be recovered
quantitatively by simple filtration, and can be regenerated and
reused. Thus, these polymer-supported hypervalent iodine reagents
are very useful, effective, and environmentally benign reagents
for organic synthesis.
1 Introduction
2 Polymer-Supported Reagents Bearing (Diacetoxy)iodo
3 Polymer-Supported Reagents Bearing (Dihalo)iodo Groups
4 Polymer-Supported Reagents Bearing (Hydroxy)(tosyl-
5 Polymer-Supported Reagents Bearing Aryliodonium
6 Polymer-Supported Reagents Bearing 1,2-Benziodoxol-3-
7 Polymer-Supported Reagents Bearing Hypervalent Iodine
Key words
polymer supported reagents - hypervalent iodine - oxidation
References
1a Umemoto T.
Yuki Gosei Kagaku Kyokaishi
1983,
41:
251
1b Varvoglis A.
Synthesis
1984,
709
1c Ochiai M.
Nagao Y.
Yuki Gosei Kagaku Kyokaishi
1986,
44:
660
1d Moriarty RM.
Vaid RK.
Synthesis
1990,
431
1e Moriarty RM.
Vaid RK.
Koser GF.
Synlett
1990,
365
1f Stang PJ.
Angew. Chem., Int. Ed. Engl.
1992,
31:
274
1g Kitamura T.
Yuki
Gosei Kagaku Kyokaishi
1995,
53:
893
1h Stang PJ.
Zhdankin VV.
Chem.
Rev.
1996,
96:
1123
1i Muraki T.
Togo H.
Yokoyama M.
Rev. Heteroatom
Chem.
1997,
17:
213
1j Zhdankin VV.
Rev. Heteroatom Chem.
1997,
17:
133
1k Togo H.
Hoshina Y.
Nogami G.
Yokoyama M.
Yuki Gosei Kagaku Kyokaishi
1997,
55:
90
1l Varvoglis A.
Tetrahedron
1997,
53:
1179
1m Togo H.
Katohgi M.
Synlett
2001,
565
2a Okawara M.
Mizuta K.
Kogyo
Kagaku Zasshi
1961,
64:
232
2b Yamada Y.
Okawara M.
Makromol. Chem.
1972,
152:
153
2c Hallensleben ML.
Angew. Makromol. Chem.
1972,
27:
223
3a Togo H.
Nogami G.
Yokoyama M.
Synlett
1998,
534
3b Togo H.
Abe S.
Nogami G.
Yokoyama M.
Bull. Chem. Soc. Jpn.
1999,
72:
2351
4 Ley SV.
Thomas AW.
Finch H.
J.
Chem. Soc., Perkin Trans. 1
1999,
669
5 Ley SV.
Schucht O.
Thomas AW.
Murray PJ.
J. Chem. Soc., Perkin
Trans. 1
1999,
1251
6 Boehlow TR.
Harburn JJ.
Spilling CD.
J. Org. Chem.
2001,
66:
3111
7a Wang Guo.-P.
Chen Zhen-C .
Synth.
Commun.
1999,
29:
2859
7b Chen Da-J .
Chen Zhen-C .
Synth. Commun.
2001,
31:
421
8 Ficht S.
Mulbaier M.
Giannis A.
Tetrahedron
2001,
57:
4863
9 Tohma H.
Morioka H.
Takizawa S.
Arisawa M.
Kita Y.
Tetrahedron
2001,
57:
345
10 Tohma H.
Takizawa S.
Maegawa T.
Kita Y.
Angew. Chem. Int. Ed.
2000,
39:
1306
11 Sakuratani, K.; Togo, H unpublished
results.
12a Huang X.
Zhu Q.
J.
Chem. Res., Synop.
2000,
300
12b Huang X.
Zhu Q.
Synth. Commun.
2001,
31:
111
13 Okawara M.
Kurusu Y.
Imoto A.
Kogyo
Kagaku Zasshi
1962,
65:
1647
14 Sket B.
Zupan M.
Zupet P.
Tetrahedron
1984,
40:
1603
15a Zupan M.
Pollak A.
J.
Chem. Soc., Chem. Commun.
1975,
715
15b Zupan M.
Collect.
Czech. Chem. Commun.
1977,
266
16a Abe S.
Sakuratani K.
Togo H.
Synlett
2001,
22
16b Abe S.
Sakuratani K.
Togo H.
J.
Org. Chem.
2001,
66:
6174
17 Chen Da-H.
Chen Zhen-C.
Synlett
2000,
1175
18 Huang X.
Zhu Q.
Tetrahedron Lett.
2001,
42:
6373
19a Moss RA.
Bolikal D.
Durst HD.
Hovance JW.
Tetrahedron Lett.
1988,
29:
2433
19b Moss RA.
Chung Y.-C.
J. Org.
Chem.
1990,
55:
2064
19c Moss RA.
Chung Y.-C.
Langmuir
1990,
6:
1614
19d Moss RA.
Zhang H.
J. Am. Chem.
Soc.
1994,
116:
4471
20 Sorg G.
Mengel A.
Jung G.
Rademann J.
Angew. Chem. Int. Ed.
2001,
40:
4395
21 Mülbair M.
Giannis A.
Angew. Chem. Int. Ed.
2001,
40:
4393
22a Kirschning A.
Jesberger M.
Monenschein H.
Tetrahedron Lett.
1999,
40:
8999
22b Kirschning A.
Monenschein H.
Schmeck C.
Angew.
Chem. Int. Ed.
1999,
38:
2594
22c Monenschein H.
Sourkouni-Argirusi G.
Schubothe KM.
O’Hare T.
Kirschning A.
Org. Lett.
1999,
1:
2101
23a Harrison CR.
Hodge P.
J.
Chem. Soc., Perkin Trans. 1
1982,
509
23b Karalkar NB.
Salunkhe MM.
Indian
J. Chem., Sect. B
1998,
37:
1184
24a Sket B.
Zupet P.
Zupan M.
J. Chem. Soc., Perkin Trans. 1
1989,
2279
24b Sket B.
Zupet P.
Zupan M.
Tetrahedron
1990,
46:
2503
