DDQ as a versatile and easily recyclable oxidant: a systematic review

Alsharif, Meshari A.; Raja, Qandeel Alam; Majeed, Nida Abdul; Jassas, Rabab S.; Alsimaree, Abdulrahman A.; Sadiq, Amina; Naeem, Nafeesa; Mughal, Ehsan Ullah; Alsantali, Reem I.; Moussa, Ziad; Ahmed, Saleh

doi:10.1039/d1ra04575j

Cited by 51 publications

(39 citation statements)

References 117 publications

(176 reference statements)

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“…As nitrogen-containing polycyclic aromatic compounds have been gaining continuously increasing interest [37,38], we decided to dehydrogenate this compound to the fully conjugated compound 7. We found that this compound is formed in a 68% yield from the reaction of 6 with DDQ [39] in the refluxing dioxane.…”

Section: Dehydrogenation Ofmentioning

confidence: 85%

Electrophile-Dependent Reactivity of Lithiated N-Benzylpyrene-1-Carboxamide

et al. 2022

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In this paper, we describe the lithiation of N-benzylpyrene-1-carboxamide with RLi-TMEDA. We found that the reaction outcome strongly depends on the electrophile used in the quenching step. The electrophile can be introduced at either the benzylic position or at the C-2 position in the pyrene nucleus. Furthermore, when H+ was used as the quencher, the product of the intramolecular carbolithiation of the pyrene K-region was formed. Dehydrogenation of the obtained compound with DDQ allowed the synthesis of a novel nitrogen polycyclic compound with an aza-benzo[c,d]pyrene (azaolympicene) skeleton. Attempts to extend the reaction scope to the amides substituted in the phenyl ring 8a and 8b gave an unexpected result. The reaction of both compounds with BuLi gave 1-valerylpyrene (9) in good yield. Photophysical properties, including absorption spectra, emission spectra and quantum yields of the emission of selected products, were studied and discussed.

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Section: Dehydrogenation Ofmentioning

confidence: 85%

Electrophile-Dependent Reactivity of Lithiated N-Benzylpyrene-1-Carboxamide

et al. 2022

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“…To this end, we utilized a recently reported acid-catalyzed domino reaction of 2-methylfuran (2) with unsaturated ketones 1 that led to the formation of furylalkanones A (Scheme 2). We screened various oxidants in order to obtain respective unsaturated products 3 from alkanones A [34][35][36] and found that DDQ in the amount of 1.2 equiv. effectively induced the desired transformation affording compounds 3 with high yields.…”

Section: Resultsmentioning

confidence: 99%

Synthetic strategy toward furyl- and benzofuryl-containing building blocks for organic materials

et al. 2022

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A synthetic approach to furyl- and benzofuryl-containing building blocks utilizing easily accessible substrates is reported. Cascade acid-catalyzed reactions of 2-methylfuran with α,β-unsaturated carbonyl compounds or salicyl alcohols followed by oxidation afford functionalized furans and benzofurans, respectively. Synthetic potential of the obtained products was demonstrated by synthesizing hetaryl-substituted heterocycles, which may find an application in materials chemistry.

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“…Decreasing the amount of Yb(OTf) 3 or elevating the reaction temperature led to inferior results (not listed). As a means to make the benzylic position of 13 a more electrophilic, we came up with an idea that 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) [13] might induce oxidative cycloisomerization as shown in Scheme To our delight, we were able to achieve clean transformation of 13 a to 14 a [14] with DDQ (1 equiv.) at room temperature (entry 5).…”

Section: Resultsmentioning

confidence: 99%

Regioselective Synthesis of 1‐Cyano‐3‐arylindolizines: Construction of Pyrroles via DDQ‐Mediated Ring Closure of Cyclopropyl Pyridines

Joshi

Kim

2022

Adv Synth Catal

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A modular approach to a wide range of 1‐cyano‐3‐(hetero)arylindolizines through aldol‐cyclopropanation‐oxidative cycloisomerization is described where DDQ was utilized for the regioselective synthesis of the pyrrole units from cyclopropyl pyridines for the first time. A key to success is regioselective oxidation of benzylic position by DDQ, which enabled us to access to one regioisomer out of two possible ones. Homo‐dimerization at the C2, C5, or C7 sites of indolizines in the presence of DDQ has been discovered for the first time as well.

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DDQ as a versatile and easily recyclable oxidant: a systematic review

Abstract: DDQ is the most widely used quinone with a high reduction potential and it mediates hydride transfer reactions and shows three accessible oxidation states: quinone (oxidized), semiquinone (one-electron-reduced) and hydroquinone (two-electron-reduced).

Cited by 51 publications

References 117 publications

Electrophile-Dependent Reactivity of Lithiated N-Benzylpyrene-1-Carboxamide

Electrophile-Dependent Reactivity of Lithiated N-Benzylpyrene-1-Carboxamide

Synthetic strategy toward furyl- and benzofuryl-containing building blocks for organic materials

Regioselective Synthesis of 1‐Cyano‐3‐arylindolizines: Construction of Pyrroles via DDQ‐Mediated Ring Closure of Cyclopropyl Pyridines

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