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Synlett 2007(17): 2764-2765
DOI: 10.1055/s-2007-991080
DOI: 10.1055/s-2007-991080
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York
[Hydroxy(tosyloxy)iodo]benzene (HTIB)
Further Information
Publication History
Publication Date:
27 September 2007 (online)
Biographical Sketches
Introduction
[Hydroxy(tosyloxy)iodo]benzene (HTIB), one of the most significant reagents among the family of hypervalent iodine reagents, has been widely used as an effective oxidant in the synthesis of various organic compounds. HTIB was first discovered in 1970 by Neiland and Karele. [1] A few years later, Koser and co-workers discovered that HTIB is an efficient reagent in organic synthesis, so in contemporary literature HTIB is often referred to as ‘Koser’s Reagent’.
Preparation:
Properties:
Abstracts
(A) A facile, general and high-yielding protocol for the synthesis of novel α-tosyloxy β-keto sulfones is described utilizing the relatively non-toxic HTIB under solvent-free conditions at room temperature. [2] |
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(B) Reaction of various ketones with HTIB followed by treatment of the α-tosyloxy ketones thus generated in situ with sodium azide, possibly in the presence of a phase-transfer catalyst, at room temperature offers a one-pot procedure for the synthesis of α-azido ketones. [3] [4] |
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(C) Ketones react with HTIB in DMSO-H2O to afford α-hydroxy ketones under neutral conditions and in good yields. [5] |
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(D) Spirodienones bearing a 1-azaspiro[4.5]decane ring have been synthesized from N-methoxy-(4-halogenophenyl)amides by the intramolecular ipso attack of a nitrenium ion generated with HTIB in trifluoroethanol. [6] |
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(E) The treatment of aryl alkenes with HTIB in 95% methanol affords the corresponding α-aryl ketones. This oxidative rearrangement is general for acyclic and cyclic aryl alkenes and permits regioselective synthesis of isomeric α-phenyl ketone pairs. [7] |
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(F) Polycyclic aromatic hydrocarbons (PAH) undergo regioselective oxidative substitution with HTIB in dichloromethane to give the corresponding aryl sulfonate esters. [8] |
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(G) Oxidation of 3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones with HTIB in CH2Cl2 leads to cyclization, thereby providing a new and convenient route for the synthesis of 3-aryl-7-methylpyrano[4,3-b]pyran-4H,5H-diones. [9] |
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(H) Oxidation of flavanones to flavones was developed using HTIB in ionic liquid 1,3-di-n-butylimidazolium bromide at room temperature. [10] |
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(I) The oxidation of benzylic alcohols with HTIB provides a rapid and convenient method to prepare corresponding carbonyl compounds under solvent-free conditions. [11] |
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(J) A novel and direct method for the synthesis of α-halocarbonyl compounds using sequential treatment of carbonyl compounds with HTIB followed by magnesium halides under solvent-free conditions. [12] |
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- 1
Neiland O.Karele B. J. Org. Chem. USSR (Engl. Transl.) 1970, 6: 889 - 2
Kumar D.Sundaree S.Patel G.Rao VS.Varma RS. Tetrahedron Lett. 2006, 47: 8239 - 3
Prakash O.Pannu K.Prakash R.Batra A. Molecules 2006, 11: 523 - 4
Kumar D.Sundaree S.Rao VS. Synth. Commun. 2006, 36: 1893 - 5
Xie YY.Chen ZC. Synth. Commun. 2002, 32: 1875 - 6
Miyazawa E.Sakamoto T.Kikugawa Y. J. Org. Chem. 2003, 68: 5429 - 7
Justik MW.Koser GF. Tetrahedron Lett. 2004, 45: 6159 - 8
Koser GF.Telu S.Laali KK. Tetrahedron Lett. 2006, 47: 7011 - 9
Prakash O.Kumar A.Sadana AK.Singh SP. Synthesis 2006, 21 - 10
Muthukrishnan M.Patil PS.More SV.Joshi RA. Mendeleev Commun. 2005, 100 - 11
Lee JC.Lee JY.Lee SJ. Tetrahedron Lett. 2004, 45: 4939 - 12
Lee JC.Park JY.Yoon SY.Bae YH.Lee SJ. Tetrahedron Lett. 2004, 45: 191
References
- 1
Neiland O.Karele B. J. Org. Chem. USSR (Engl. Transl.) 1970, 6: 889 - 2
Kumar D.Sundaree S.Patel G.Rao VS.Varma RS. Tetrahedron Lett. 2006, 47: 8239 - 3
Prakash O.Pannu K.Prakash R.Batra A. Molecules 2006, 11: 523 - 4
Kumar D.Sundaree S.Rao VS. Synth. Commun. 2006, 36: 1893 - 5
Xie YY.Chen ZC. Synth. Commun. 2002, 32: 1875 - 6
Miyazawa E.Sakamoto T.Kikugawa Y. J. Org. Chem. 2003, 68: 5429 - 7
Justik MW.Koser GF. Tetrahedron Lett. 2004, 45: 6159 - 8
Koser GF.Telu S.Laali KK. Tetrahedron Lett. 2006, 47: 7011 - 9
Prakash O.Kumar A.Sadana AK.Singh SP. Synthesis 2006, 21 - 10
Muthukrishnan M.Patil PS.More SV.Joshi RA. Mendeleev Commun. 2005, 100 - 11
Lee JC.Lee JY.Lee SJ. Tetrahedron Lett. 2004, 45: 4939 - 12
Lee JC.Park JY.Yoon SY.Bae YH.Lee SJ. Tetrahedron Lett. 2004, 45: 191