Solvent-free synthesis of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one from Dess–Martin periodinane and its synthetic utility for α-tosyloxylation of ketones

Karade, Nandkishor N.; Tiwari, Girdharilal B.; Shinde, Sandeep V.; Gampawar, Sumeet V.; Kondre, Jeevan M.

doi:10.1016/j.tetlet.2008.03.119

Cited by 13 publications

(6 citation statements)

References 35 publications

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“…The introduction of various oxygen functionalities such as tosyloxy, mesyloxy, acetoxy, phosphoryloxy, methoxy, ethoxy and isopropoxy at the α‐position of β‐dicarbonyl compounds is an important transformation in organic synthesis since the resulting products are the key intermediates for the synthesis of a variety of heterocyclic1 and natural products 2. Methods for the direct α‐tosyloxylation of β‐dicarbonyl compounds involve the use of various reagents such as N ‐methyl‐ O ‐tosylhydroxylamine,3 hydroxy(tosyloxy)iodobenzene (HTIB)4,5 and 1‐( p ‐toluenesulfonyloxy)‐1,2‐benziodoxol‐3(1 H )‐one 6. [Hydroxy(mesyloxy)iodo]benzene (HMIB)7 is used for the preparation of α‐mesyloxylated β‐dicarbonyl compounds.…”

Section: Introductionmentioning

confidence: 99%

Various α‐Oxygen Functionalizations of β‐Dicarbonyl Compounds Mediated by the Hypervalent Iodine(III) Reagent p‐Iodotoluene Difluoride with Different Oxygen‐Containing Nucleophiles

Tian

Zhang

2010

Adv Synth Catal

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p-Iodotoluene difluoride (p-Tol-IF 2 ) has been found to be a general reagent for the effective introduction of various oxygen-containing functionalities including tosyloxy, mesyloxy, acetoxy, phosphoryloxy, methoxy, ethoxy and isopropoxy at the a-position of b-dicarbonyl compounds. These transformations can be readily realized by the use of the combined reagent of p-iodotoluene difluoride and various oxygen-containing nucleophilic compounds such as p-toluenesulfonic acid, methanesulfonic acid, acetic acid, diphenyl phosphate, methanol, ethanol and propan-2-ol under mild conditions, respectively. And, the in situ generated hypervalent iodineA C H T U N G T R E N N U N G (III) species via ligand exchange between p-iodotoluene difluoride and the respective oxygen-containing nucleophiles are believed to be the real oxidizing agents in such transformations.

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Section: Introductionmentioning

confidence: 99%

Various α‐Oxygen Functionalizations of β‐Dicarbonyl Compounds Mediated by the Hypervalent Iodine(III) Reagent p‐Iodotoluene Difluoride with Different Oxygen‐Containing Nucleophiles

Tian

Zhang

2010

Adv Synth Catal

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“…Karade and co-workers studied the tosyloxylation of ketones with reagent 3 in details (eqn (1)). 17 Good yields were obtained for aromatic and aliphatic ketones, as well as for ketoesters.…”

Section: C-heteroatom Bond Formationmentioning

confidence: 97%

“…Karade and coworkers studied the tosyloxylation of ketones with reagent 3 in details (eqn 1). 17 Good yields were obtained for aromatic 40 and aliphatic ketones, as well as for ketoesters. Several other examples of tosyloxylation reactions using  3 or  5 -benziodoxole-based compounds were reported, but in these cases the active reagent was formed in situ.…”

mentioning

confidence: 97%

Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions

et al. 2011

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In the last decades, hypervalent iodine reagents have raised from chemical curiosities to mainstream reagents in organic synthesis. The use of benziodoxole-derived reagents has been especially successful in oxidation methods, whereas non-cyclic iodinanes have been used both for oxidation and atom-transfer reactions. On the other hand, the exceptional properties of 10 benziodoxole reagents for atom-transfer reactions have only started to attract the attention of the synthetic community more recently. In this review, progress in the use of these compounds for C-X and C-C bond formations will be presented. In particular, recent breakthroughs in trifluoromethylation and alkynylation reactions have been realized since 2006 bas ed on benziodoxole-derived reagents and these results are the main focus of this article.

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“…Similarly, (diacetoxyiodo)benzene has been reported for the oxidative aromatization of 1,3,5‐trisubstituted pyrazolines [12] and 2‐imidazolines [13]. Recently, we have reported a clean and efficient oxidative dehydrogenation of 3,4‐dihydropyrimidin‐2(1 H )‐ones to 1,2‐dihydropyrimidines using a combination of (diacetoxyiodo)benzene and tert ‐butylhydroperoxide in CH 2 Cl 2 [14]. The application of hypervalent iodine reagents for the oxidative aromatization of 1,4‐dihydropyrimidines is hitherto unknown in the literature.…”

Section: Introductionmentioning

confidence: 94%

Mild and efficient oxidative aromatization of 4‐substituted‐1,4‐dihydropyrimidines using (diacetoxyiodo)benzene

Karade¹,

Gampawar²,

Tale³

et al. 2010

Journal of Heterocyclic Chem

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Solvent-free synthesis of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one from Dess–Martin periodinane and its synthetic utility for α-tosyloxylation of ketones

Cited by 13 publications

References 35 publications

Various α‐Oxygen Functionalizations of β‐Dicarbonyl Compounds Mediated by the Hypervalent Iodine(III) Reagent p‐Iodotoluene Difluoride with Different Oxygen‐Containing Nucleophiles

Various α‐Oxygen Functionalizations of β‐Dicarbonyl Compounds Mediated by the Hypervalent Iodine(III) Reagent p‐Iodotoluene Difluoride with Different Oxygen‐Containing Nucleophiles

Benziodoxole-based hypervalent iodine reagents for atom-transfer reactions

Mild and efficient oxidative aromatization of 4‐substituted‐1,4‐dihydropyrimidines using (diacetoxyiodo)benzene

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