DDQ catalyzed benzylic acetoxylation of arylalkanes: a case of exquisitely controlled oxidation under sonochemical activation

Kumar, Vinod; Sharma, Abhishek; Sharma, Meenakshi; Sharma, Upendra; Sinha, Arun K.

doi:10.1016/j.tet.2007.07.018

Cited by 53 publications

(18 citation statements)

References 73 publications

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“…Therefore, recently, ultrasonic irradiation technique has received considerable attention of researchers. [21][22][23][24][25] In continuation of our ongoing research on the Michael addition of imides and amides to unsaturated systems, 26,27 we report here an efficient strategy for synthesis of a series of DPH derivatives by Michael addition of this compound to α,β-unsaturated esters under ultrasound irradiation (Scheme 2).…”

Section: Scheme 1 Nucleophilic Reactions Of Diverse Positions Of Dphmentioning

confidence: 99%

Solvent-free highly regioselective Michael addition of phenytoin to α,β-unsaturated esters in the presence of TBAB under ultrasound irradiation

Imanzadeh¹,

Rezaee-Gatar²

2015

Arkivoc

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The highly regioselective C-N bond formation between phenytoin and acrylic/fumaric esters was accomplished. Solvent-free media Michael addition of phenytoin to acrylic esters led to the selective synthesis of N3-substituted phenytoins (as mono-Michael adducts) in the presence of tetrabutylammonium bromide (TBAB) and potassium carbonate under ultrasonic irradiation conditions at room temperature. These reactions produced N1,N3-disubstituted phenytoins (as bis-Michael adducts) at 70 ºC. Surprisingly, the addition of phenytoin to fumaric esters, instead of acrylic esters, selectively provided only N3-substituted phenytoins at both room temperature and 70 ºC under the same conditions.

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Section: Scheme 1 Nucleophilic Reactions Of Diverse Positions Of Dphmentioning

confidence: 99%

Solvent-free highly regioselective Michael addition of phenytoin to α,β-unsaturated esters in the presence of TBAB under ultrasound irradiation

Imanzadeh¹,

Rezaee-Gatar²

2015

Arkivoc

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“…For example, the acetoxylation of alkylarenes 283 with DDQ in acetic acid under ultrasound irradiation produced acetates 284 ( Scheme 63 ) [ 241 ].…”

Section: Reviewmentioning

confidence: 99%

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

Krylov

Vil

Terent’ev

2015

Beilstein J. Org. Chem.

168

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SummaryThe present review summarizes primary publications on the cross-dehydrogenative C–O coupling, with special emphasis on the studies published after 2000. The starting compound, which donates a carbon atom for the formation of a new C–O bond, is called the CH-reagent or the C-reagent, and the compound, an oxygen atom of which is involved in the new bond, is called the OH-reagent or the O-reagent. Alcohols and carboxylic acids are most commonly used as O-reagents; hydroxylamine derivatives, hydroperoxides, and sulfonic acids are employed less often. The cross-dehydrogenative C–O coupling reactions are carried out using different C-reagents, such as compounds containing directing functional groups (amide, heteroaromatic, oxime, and so on) and compounds with activated C–H bonds (aldehydes, alcohols, ketones, ethers, amines, amides, compounds containing the benzyl, allyl, or propargyl moiety). An analysis of the published data showed that the principles at the basis of a particular cross-dehydrogenative C–O coupling reaction are dictated mainly by the nature of the C-reagent. Hence, in the present review the data are classified according to the structures of C-reagents, and, in the second place, according to the type of oxidative systems. Besides the typical cross-dehydrogenative coupling reactions of CH- and OH-reagents, closely related C–H activation processes involving intermolecular C–O bond formation are discussed: acyloxylation reactions with ArI(O2CR)2 reagents and generation of O-reagents in situ from C-reagents (methylarenes, aldehydes, etc.).

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“…Since Sinha and co-workers reported a 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) promoted acetoxylation of arylalkanes under sonochemical activation conditions in the absence of metal catalyst [12], various efficient esterification methods have been developed under metal-free conditions. The combination of quaternary ammonium iodides with strong oxidants was found to be an effective strategy for direct esterification and amination of benzylic C-H bonds [13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

An Efficient Metal-Free Oxidative Esterification and Amination of Benzyl C–H Bond

Liu

Chen²,

et al. 2020

Molecules

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An esterification and amination of benzylic C–H bonds was developed by using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under metal- and iodide-free conditions. Both carboxylic acids and amines could be used as ideal coupling partners for the oxidative coupling reactions with various diarylmethanes. A close to equal amount of coupling reagents was enough to afford the product in good to high yields.

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DDQ catalyzed benzylic acetoxylation of arylalkanes: a case of exquisitely controlled oxidation under sonochemical activation

Cited by 53 publications

References 73 publications

Solvent-free highly regioselective Michael addition of phenytoin to α,β-unsaturated esters in the presence of TBAB under ultrasound irradiation

Solvent-free highly regioselective Michael addition of phenytoin to α,β-unsaturated esters in the presence of TBAB under ultrasound irradiation

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

An Efficient Metal-Free Oxidative Esterification and Amination of Benzyl C–H Bond

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