Polymer-Supported Hypervalent Iodine Reagents

Hideo  Togo; Kenji  Sakuratani

doi:10.1055/s-2002-35575

ACCOUNT

Polymer-Supported Hypervalent Iodine Reagents

Hideo Togo*^a,b, Kenji Sakuratani^a
Graduate School of Science and Technology, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522 Japan
Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522 Japan
Fax: +81(43)2902874; e-Mail: togo@scichem.s.chiba-u.ac.jp;

Abstract

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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
Groups
3 Polymer-Supported Reagents Bearing (Dihalo)iodo Groups
4 Polymer-Supported Reagents Bearing (Hydroxy)(tosyl-
oxy)iodo Groups and (Hydroxy)(phosphoryloxy)iodo
Groups
5 Polymer-Supported Reagents Bearing Aryliodonium
Groups
6 Polymer-Supported Reagents Bearing 1,2-Benziodoxol-3-
one Groups
7 Polymer-Supported Reagents Bearing Hypervalent Iodine
Groups as Counter Anion

Key words

polymer supported reagents - hypervalent iodine - oxidation

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References

<A NAME="RA29902ST-1A">1a</A> Umemoto T. Yuki Gosei Kagaku Kyokaishi 1983, 41: 251

<A NAME="RA29902ST-1B">1b</A> Varvoglis A. Synthesis 1984, 709

<A NAME="RA29902ST-1C">1c</A> Ochiai M. Nagao Y. Yuki Gosei Kagaku Kyokaishi 1986, 44: 660

<A NAME="RA29902ST-1D">1d</A> Moriarty RM. Vaid RK. Synthesis 1990, 431

<A NAME="RA29902ST-1E">1e</A> Moriarty RM. Vaid RK. Koser GF. Synlett 1990, 365

<A NAME="RA29902ST-1F">1f</A> Stang PJ. Angew. Chem., Int. Ed. Engl. 1992, 31: 274

<A NAME="RA29902ST-1G">1g</A> Kitamura T. Yuki Gosei Kagaku Kyokaishi 1995, 53: 893

<A NAME="RA29902ST-1H">1h</A> Stang PJ. Zhdankin VV. Chem. Rev. 1996, 96: 1123

<A NAME="RA29902ST-1I">1i</A> Muraki T. Togo H. Yokoyama M. Rev. Heteroatom Chem. 1997, 17: 213

<A NAME="RA29902ST-1J">1j</A> Zhdankin VV. Rev. Heteroatom Chem. 1997, 17: 133

<A NAME="RA29902ST-1K">1k</A> Togo H. Hoshina Y. Nogami G. Yokoyama M. Yuki Gosei Kagaku Kyokaishi 1997, 55: 90

<A NAME="RA29902ST-1L">1l</A> Varvoglis A. Tetrahedron 1997, 53: 1179

<A NAME="RA29902ST-1M">1m</A> Togo H. Katohgi M. Synlett 2001, 565

<A NAME="RA29902ST-2A">2a</A> Okawara M. Mizuta K. Kogyo Kagaku Zasshi 1961, 64: 232

<A NAME="RA29902ST-2B">2b</A> Yamada Y. Okawara M. Makromol. Chem. 1972, 152: 153

<A NAME="RA29902ST-2C">2c</A> Hallensleben ML. Angew. Makromol. Chem. 1972, 27: 223

<A NAME="RA29902ST-3A">3a</A> Togo H. Nogami G. Yokoyama M. Synlett 1998, 534

<A NAME="RA29902ST-3B">3b</A> Togo H. Abe S. Nogami G. Yokoyama M. Bull. Chem. Soc. Jpn. 1999, 72: 2351

<A NAME="RA29902ST-4">4</A> Ley SV. Thomas AW. Finch H. J. Chem. Soc., Perkin Trans. 1 1999, 669

<A NAME="RA29902ST-5">5</A> Ley SV. Schucht O. Thomas AW. Murray PJ. J. Chem. Soc., Perkin Trans. 1 1999, 1251

<A NAME="RA29902ST-6">6</A> Boehlow TR. Harburn JJ. Spilling CD. J. Org. Chem. 2001, 66: 3111

<A NAME="RA29902ST-7A">7a</A> Wang Guo.-P. Chen Zhen-C . Synth. Commun. 1999, 29: 2859

<A NAME="RA29902ST-7B">7b</A> Chen Da-J . Chen Zhen-C . Synth. Commun. 2001, 31: 421

<A NAME="RA29902ST-8">8</A> Ficht S. Mulbaier M. Giannis A. Tetrahedron 2001, 57: 4863

<A NAME="RA29902ST-9">9</A> Tohma H. Morioka H. Takizawa S. Arisawa M. Kita Y. Tetrahedron 2001, 57: 345

<A NAME="RA29902ST-10">10</A> Tohma H. Takizawa S. Maegawa T. Kita Y. Angew. Chem. Int. Ed. 2000, 39: 1306

Sakuratani, K.; Togo, H unpublished results.

<A NAME="RA29902ST-12A">12a</A> Huang X. Zhu Q. J. Chem. Res., Synop. 2000, 300

<A NAME="RA29902ST-12B">12b</A> Huang X. Zhu Q. Synth. Commun. 2001, 31: 111

<A NAME="RA29902ST-13">13</A> Okawara M. Kurusu Y. Imoto A. Kogyo Kagaku Zasshi 1962, 65: 1647

<A NAME="RA29902ST-14">14</A> Sket B. Zupan M. Zupet P. Tetrahedron 1984, 40: 1603

<A NAME="RA29902ST-15A">15a</A> Zupan M. Pollak A. J. Chem. Soc., Chem. Commun. 1975, 715

<A NAME="RA29902ST-15B">15b</A> Zupan M. Collect. Czech. Chem. Commun. 1977, 266

<A NAME="RA29902ST-16A">16a</A> Abe S. Sakuratani K. Togo H. Synlett 2001, 22

<A NAME="RA29902ST-16B">16b</A> Abe S. Sakuratani K. Togo H. J. Org. Chem. 2001, 66: 6174

<A NAME="RA29902ST-17">17</A> Chen Da-H. Chen Zhen-C. Synlett 2000, 1175

<A NAME="RA29902ST-18">18</A> Huang X. Zhu Q. Tetrahedron Lett. 2001, 42: 6373

<A NAME="RA29902ST-19A">19a</A> Moss RA. Bolikal D. Durst HD. Hovance JW. Tetrahedron Lett. 1988, 29: 2433

<A NAME="RA29902ST-19B">19b</A> Moss RA. Chung Y.-C. J. Org. Chem. 1990, 55: 2064

<A NAME="RA29902ST-19C">19c</A> Moss RA. Chung Y.-C. Langmuir 1990, 6: 1614

<A NAME="RA29902ST-19D">19d</A> Moss RA. Zhang H. J. Am. Chem. Soc. 1994, 116: 4471

<A NAME="RA29902ST-20">20</A> Sorg G. Mengel A. Jung G. Rademann J. Angew. Chem. Int. Ed. 2001, 40: 4395

<A NAME="RA29902ST-21">21</A> Mülbair M. Giannis A. Angew. Chem. Int. Ed. 2001, 40: 4393

<A NAME="RA29902ST-22A">22a</A> Kirschning A. Jesberger M. Monenschein H. Tetrahedron Lett. 1999, 40: 8999

<A NAME="RA29902ST-22B">22b</A> Kirschning A. Monenschein H. Schmeck C. Angew. Chem. Int. Ed. 1999, 38: 2594

<A NAME="RA29902ST-22C">22c</A> Monenschein H. Sourkouni-Argirusi G. Schubothe KM. O’Hare T. Kirschning A. Org. Lett. 1999, 1: 2101

<A NAME="RA29902ST-23A">23a</A> Harrison CR. Hodge P. J. Chem. Soc., Perkin Trans. 1 1982, 509

<A NAME="RA29902ST-23B">23b</A> Karalkar NB. Salunkhe MM. Indian J. Chem., Sect. B 1998, 37: 1184

<A NAME="RA29902ST-24A">24a</A> Sket B. Zupet P. Zupan M. J. Chem. Soc., Perkin Trans. 1 1989, 2279

<A NAME="RA29902ST-24B">24b</A> Sket B. Zupet P. Zupan M. Tetrahedron 1990, 46: 2503