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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Review Article

Hypervalent Iodine Reagents in the Synthesis of Flavonoids and Related Compounds

Author(s): Rajesh Kumar, Nitya Sharma and Om Prakash*

Volume 24, Issue 18, 2020

Page: [2031 - 2047] Pages: 17

DOI: 10.2174/1385272824999200420074551

Price: $65

Abstract

Hypervalent iodine compounds have proved to be very useful reagents to bring about various oxidative transformations including (i) α-functionalization of carbonyl compounds, (ii) oxidation of phenols, and (iii) oxidative rearrangement of ketones and α,β- unsaturated ketones. These reactions find interesting applications in the development of newer and convenient approaches for the synthesis of flavonoids. This review focuses on the use of most common three hypervalent compounds, namely iodobenzene diacetate, [hydroxy(tosyloxy)iodo]benzene, and [bis-trifluoroacetoxy(iodo)]benzene in the synthesis of cis/trans-3-hydroxyflavanones, 3-hydroxyflavones (flavonols), flavones, isoflavones and related compounds.

Keywords: Hypervalent iodine compounds, flavones, isoflavones, flavonols, chalcones, [hydroxy(tosyloxy)iodo]benzene.

Graphical Abstract
[1]
Kumar, R.; Sharma, N.; Prakash, O. Hypervalent iodine reagents in the synthesis of flavonoids and related compounds. Curr. Org. Chem., 2020, 24(18), 2031-2047.
[http://dx.doi.org/10.2174/1385272824999200420074551]
[2]
Saito, A. Hypervalent iodine-mediated/catalyzed oxidative cycloisomerization/annulation of alkynes for metal-free synthesis of oxazoles. Curr. Org. Chem., 2020, 24(18), 2048-2069.
[http://dx.doi.org/10.2174/1385272824999200510232438]
[3]
Wang, Y.; An, G.; Wang, L.; Han, J.W. Diaryliodonium salts: structures and synthesis. Curr. Org. Chem., 2020, 24(18), 2070-2105.
[http://dx.doi.org/10.2174/1385272824999200507124328]
[4]
Zheng, H.; Xue, X-S. Recent computational studies on the mechanism of hypervalent iodine mediated dearomatization of phenols. Curr. Org. Chem., 2020, 24(18), 2106-2117.
[http://dx.doi.org/10.2174/1385272824999200620223218]
[5]
Yamada, S.; Konno, S. Recent advances in halogen bond-assisted organic synthesis. Curr. Org. Chem., 2020, 24(18), 2118-2152.
[http://dx.doi.org/10.2174/1385272823666191209112543]
[6]
Yamamoto, Y.; Kawaguchi, S.; Kodama, S.; Nomoto, A.; Ogawa, A. Highly selective hydroiodination of carbon–carbon double or triple bonds. Curr. Org. Chem., 2020, 24(18), 2153-2168.
[http://dx.doi.org/10.2174/1385272824666191227111257]
[7]
Tarui, A.; Karuo, Y.; Sato, K.; Kawai, K.; Omote, M. Stereoselective synthesis of multisubstituted α-fluoro-β-lactams. Curr. Org. Chem., 2020, 24(18), 2169-2180.
[http://dx.doi.org/10.2174/1385272824666200221114707]
[8]
Wang, L.; Li, Z.; Liu, J.; Han, J.; Moriwaki, H.; Soloshonok, V.A. Recent developments in the asymmetric detrifluoroacetylative reactions of in situ generated mono-fluorinated enolates. Curr. Org. Chem., 2020, 24(18), 2181-2191.
[http://dx.doi.org/10.2174/1385272824999200801022712]

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