m-Iodosylbenzoic
Acid as a Convenient Recyclable Hypervalent Iodine Oxidant for the
Synthesis of α-Iodo Ketones by Oxidative Iodination of
Ketones

Mehman S. Yusubov; Rosa Y. Yusubova; Tatyana V. Funk; Ki-Whan Chi; Andreas Kirschning; Viktor V. Zhdankin

doi:10.1055/s-0030-1258223

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2010(21): 3681-3685
DOI: 10.1055/s-0030-1258223

PAPER

m-Iodosylbenzoic Acid as a Convenient Recyclable Hypervalent Iodine Oxidant for the Synthesis of α-Iodo Ketones by Oxidative Iodination of Ketones

Mehman S. Yusubov*^a, Rosa Y. Yusubova^a, Tatyana V. Funk^a, Ki-Whan Chi^b, Andreas Kirschning^c, Viktor V. Zhdankin*^d
^a The Siberian State Medical University and Tomsk Polytechnic University, 2 Moskovsky trakt, 634050 Tomsk, Russian Federation
e-Mail: yusubov@mail.ru;
^b University of Ulsan, 680-749 Ulsan, Republic of Korea
^c Institut für Organische Chemie, Leibniz Universität Hannover, Schneiderberg 1b, 30167 Hannover, Germany
^d Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA
Fax: +1(218)7267394; e-Mail: vzhdanki@d.umn.edu;

Further Information

Publication History

Received 9 June 2010
Publication Date:
20 August 2010 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A convenient procedure for the preparation of α-iodo ketones by oxidative iodination of ketones using iodine and m-iodosylbenzoic acid as a recyclable hypervalent iodine oxidant is reported. Various ketones and β-dicarbonyl compounds can be iodinated by this reagent system under mild conditions affording the respective α-iodo-substituted carbonyl compounds in excellent yields. The final products of iodination are conveniently separated from byproducts by simple treatment with anionic exchange resin Amberlite IRA 900 HCO₃ ^- and are isolated with good purity after evaporation of the solvent. The reduced form of the hypervalent iodine oxidant, m-iodobenzoic acid, can be recovered in 91-95% yield from the Amberlite resin by treatment with aqueous hydrochloric acid followed by extraction with ethyl acetate.

Key words

halogenation - iodine - ketones - iodosylbenzene - m-iodosylbenzoic acid - hypervalent iodine

References

1a Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis, In Topics in Current Chemistry Wirth T. Springer; Heidelberg: 2003. p.224

Google Scholar
1b Zhdankin VV. Stang PJ. Chem. Rev. 2008, 108: 5299

Google Scholar
1c Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; London: 1997.

Google Scholar
1d Koser GF. Adv. Heterocycl. Chem. 2004, 86: 225

Google Scholar
1e Zhdankin VV. Stang PJ. Chem. Rev. 2002, 102: 2523

Google Scholar
1f Ladziata U. Zhdankin VV. ARKIVOC 2006, (ix): 26

Google Scholar
1g Ochiai M. Coord. Chem. Rev. 2006, 250: 2771

Google Scholar
1h Ochiai M. Chem. Rec. 2007, 7: 12

Google Scholar
1i Ochiai M. Miyamoto K. Eur. J. Org. Chem. 2008, 4229

Google Scholar
1j Dohi T. Kita Y. Chem. Commun. 2009, 2073

Google Scholar
1k Ladziata U. Zhdankin VV. Synlett 2007, 527

Google Scholar
1l Quideau S. Pouysegu L. Deffieux D. Synlett 2008, 467

Google Scholar
1m Stang PJ. Zhdankin VV. Chem. Rev. 1996, 96: 1123

Google Scholar
1n Zhdankin VV. ARKIVOC 2009, (i): 1

Google Scholar
1o Uyanik M. Ishihara K. Chem. Commun. 2009, 2086

Google Scholar
1p Ngatimin M. Lupton DW. Aust. J. Chem. 2010, 63: 653

Google Scholar
1q Yusubov MS. Nemykin VN. Zhdankin VV. Tetrahedron 2010, 66: 5745

Google Scholar
2a Togo H. Sakuratani K. Synlett 2002, 1966

Google Scholar
2b Yamamoto Y. Kawano Y. Toy PH. Togo H. Tetrahedron 2007, 63: 4680

Google Scholar
2c Tohma H. Takizawa S. Maegawa T. Kita Y. Angew. Chem. Int. Ed. 2000, 39: 1306

Google Scholar
2d Tohma H. Morioka H. Takizawa S. Arisawa M. Kita Y. Tetrahedron 2001, 57: 345

Google Scholar
2e Tohma H. Maegawa T. Kita Y. Synlett 2003, 723

Google Scholar
2f Abe S. Sakuratani K. Togo H. J. Org. Chem. 2001, 66: 6174

Google Scholar
2g Abe S. Sakuratani K. Togo H. Synlett 2001, 22

Google Scholar
2h Sakuratani K. Togo H. ARKIVOC 2003, (vi): 11

Google Scholar
2i Sakuratani K. Togo H. Synthesis 2003, 21

Google Scholar
2j Ueno M. Togo H. Synthesis 2004, 2673

Google Scholar
2k Tashino Y. Togo H. Synlett 2004, 2010

Google Scholar
2l Shang Y. But TYS. Togo H. Toy PH. Synlett 2007, 67

Google Scholar
2m Jang H.-S. Chung W.-J. Lee Y.-S. Tetrahedron Lett. 2007, 48: 3731

Google Scholar
2n Ladziata U. Willging J. Zhdankin VV. Org. Lett. 2006, 8: 167

Google Scholar
2o Ladziata U. Zhdankin VV. Synlett 2007, 527

Google Scholar
3a Yusubov MS. Gilmkhanova MP. Zhdankin VV. Kirschning A. Synlett 2007, 563

Google Scholar
3b Kirschning A. Yusubov MS. Yusubova RY. Chi K.-W. Park JY. Beilstein J. Org. Chem. 2007, 3: 19

Google Scholar
3c Yusubov MS. Funk TV. Chi K.-W. Cha E.-H. Kim GH. Kirschning A. Zhdankin VV. J. Org. Chem. 2008, 73: 295

Google Scholar
3d Yusubov MS. Drygunova LA. Zhdankin VV. Synthesis 2004, 2289

Google Scholar
3e Yusubov MS. Zhdankin VV. Mendeleev Commun. 2010, 20: 185

Google Scholar
Representative publications:
4a Kim S. Lim CJ. Angew. Chem. Int. Ed. 2004, 43: 5378

Google Scholar
4b Kondo J. Shinokubo H. Oshima K. Angew. Chem. Int. Ed. 2003, 42: 825

Google Scholar
4c Chai W. Takeda A. Hara M. Ji S.-J. Horiuchi CA. Tetrahedron 2005, 61: 2453.

Google Scholar
4d Takami K. Yorimitsu H. Oshima K. Org. Lett. 2004, 6: 4555

Google Scholar
4e Shimizu M. Kobayashi F. Hayakawa R. Tetrahedron 2001, 57: 9591

Google Scholar
4f Kim S. Lim CJ. Song C. Chung W.-j. J. Am. Chem. Soc. 2002, 124: 14306

Google Scholar
4g De Kimpe N. Verhé R. In The Chemistry of α-Haloketones, α-Haloaldehydes and α-Haloimines 1-119: Patai S. Rappoport Z. John Wiley; Chichester: 1988.

Google Scholar
5a Bekaert A. Barberan O. Gervais M. Brion J.-D. Tetrahedron Lett. 2000, 41: 2903

Google Scholar
5b Barluenga J. Martinez-Gallo JM. Najera C. Yus M. Synthesis 1986, 678

Google Scholar
5c Horiuchi CA. Kiji S. Chem. Lett. 1988, 31

Google Scholar
6 Katritzky AR. Savage GP. Gallos JK. Durst HD. J. Chem. Soc., Perkin Trans. 2 1990, 1515

Crossref Google Scholar
7a Dalla Cort A. J. Org. Chem. 1991, 56: 6708

Google Scholar
7b Sket B. Zupet P. Zupan M. Dolenc D. Bull. Chem. Soc. Jpn. 1989, 62: 3406

Google Scholar
7c Vankar YD. Shah K. Bawa A. Singh SP. Tetrahedron 1991, 47: 8883

Google Scholar
7d Stavber G. Iskra J. Zupan M. Stavber S. Green Chem. 2009, 11: 1262

Google Scholar
7e Horiuchi CA. Takahashi E. Bull. Chem. Soc. Jpn. 1994, 67: 271

Google Scholar
7f Cardillo G. Shimizu M. J. Org. Chem. 1977, 42: 4268

Google Scholar
7g Goswami P. Ali S. Khan M. Khan AT. ARKIVOC 2007, (xv): 82

Google Scholar
7h Rubottom GM. Mott RC. J. Org. Chem. 1979, 44: 1731

Google Scholar
7i Yin G. Gao M. She N. Hu S. Wu A. Pan Y. Synthesis 2007, 3113

Google Scholar
8 Antonioletti R. D’Auria M. D’Onofrio F. Piancatelli G. Scettri A. J. Chem. Soc., Perkin Trans. 1 1986, 1755

Crossref Google Scholar
9a Kalogiannis S. Spyroudis S. J. Org. Chem. 1990, 55: 5041

Google Scholar
9b Jereb M. Zupan M. Stavber S. Chem. Commun. 2004, 2614

Google Scholar