Tandem oxidation–oxidative C–H/C–H cross-coupling: synthesis of arylquinones from hydroquinones

Shuai, Zhikang; Song, Feijie; Zhao, Dongbing; You, Jingsong

doi:10.1039/c3cc41067f

Cited by 64 publications

(35 citation statements)

References 42 publications

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“…5 24 The low performance of such uniform proton-electron mixed conducting cathodes is mainly due to their poor electronic conductivity. 22,24,26 Ruddlesden-Popper (R-P) oxides with a general formula of A n+1 B n O 3n+1 , e.g. Increasing the concentration of the altervalent dopants is certainly helpful in improving the electronic conductivity; however, impurities might also form as a secondary phase.…”

Section: Introductionmentioning

confidence: 99%

A high performance cathode for proton conducting solid oxide fuel cells

et al. 2015

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Intermediate temperature solid-oxide fuel cells (IT-SOFCs) ), as one of the energy conversion devices, have attracted worldwide interest for their great fuel efficiency, low air pollution, much reduced cost and excellent longtime stability. In the intermediate temperature range (500-700 C), SOFCs based on proton conducting electrolytes (PSOFCs) display unique advantages over those based on oxygen ion conducting electrolytes. A key obstacle to the practical operation of past P-SOFCs is the poor stability of the traditionally used composite cathode materials in the steam-containing atmosphere and their low contribution to proton conduction. Here we report the identification of a new Ruddlesden-Popper-type oxide Sr 3 Fe 2 O 7Àd that meets the requirements for much improved long-term stability and shows a superior single-cell performance. With a Sr 3 Fe 2 O 7Àd -5 wt% BaZr 0.3 Ce 0.5 Y 0.2 O 3Àd cathode, the P-SOFC exhibits high power densities (683 and 583 mW cm À2 at 700 C and 650 C, respectively) when operated with humidified hydrogen as the fuel and air as the cathode gas. More importantly, no decay in discharging was observed within a 100 hour test. † Electronic supplementary information (ESI) available: Experimental details of conductivity, oxygen permeation and electrical conductivity relaxation tests; the results of electronic conductivity, oxygen permeation rate, surface exchange coefficients, BZCY content dependence of the ohmic resistance (R o ) and the polarization resistance (R p ), experimental and t Nyquist plots. See

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Section: Introductionmentioning

confidence: 99%

A high performance cathode for proton conducting solid oxide fuel cells

et al. 2015

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“…In 2013, Song and You developed a tandem oxidation–oxidative C–H/C–H cross‐coupling protocol for the synthesis of arylquinones, which was directly arylated to in situ generate quinones (Scheme ) . This reaction demonstrated a concise and efficient protocol for the synthesis of arylquinones from widely available hydroquinones.…”

Section: Arylation Of Quinonesmentioning

confidence: 99%

Recent Advances in Direct Functionalization of Quinones

2019

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Developing methods for the direct functionalization of quinones for assembly of highly functionalized quinones or bioactive natural products is an essential topic in the field of direct C–H functionalization. Quinone units are key motifs in many bioactive compounds and materials, and many innovative methods have been elaborated for the generation of these units. A major part of the established synthetic strategies combines installation of substituents on hydroquinones, phenols, or phenyl ethers through different coupling reactions with oxidation to produce the desired quinones. Most of these above‐mentioned methods introduce multiple chemical steps; however, the synthesis of quinoid compounds through the direct C–H functionalization of simple quinones remains challenging. This minireview summarizes the recently developed achievements for assembly of functionalized quinones through direct functionalization of simple quinones. Our focus will be on the methods and mechanism of these reactions that have appeared in the last two decades.

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“…Unless otherwise noted, all reagents were obtained from commercial suppliers and used without further purification. [RhCp*Cl 2 ] 2 , 1 alkynes 2 and quinones [3][4][5][6] were prepared according to the literature procedures. DCE was dried by refluxing over CaH 2 , and freshly distilled prior to use.…”

Section: General Remarksmentioning

confidence: 99%

Rh-catalysed direct cyclisation of 1,4-naphthoquinone and 9,10-phenanthraquinone with alkyne: facile access to 1,8-dioxapyrenes and 1,12-dioxaperylenes as orange and red-emitting luminophores

et al. 2015

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Rh-catalysed direct cyclisation of 1,4-naphthoquinones and 9,10-phenanthraquinones with alkynes has been accomplished for the first time through the C-H activation strategy to forge 1,8-dioxapyrenes and 1,12-dioxaperylenes. Starting from readily available substrates, a variety of dipyran-containing PAHs are obtained in one step and exhibit orange/red-emitting performance, large Stokes shifts and high thermal stability.

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Tandem oxidation–oxidative C–H/C–H cross-coupling: synthesis of arylquinones from hydroquinones

Abstract: A concise and efficient approach to arylquinones from widely available hydroquinones has been developed through a tandem reaction involving the oxidation of hydroquinones and subsequent oxidative C-H/C-H cross-coupling of the resulting quinones with arenes.

Cited by 64 publications

References 42 publications

A high performance cathode for proton conducting solid oxide fuel cells

A high performance cathode for proton conducting solid oxide fuel cells

Recent Advances in Direct Functionalization of Quinones

Rh-catalysed direct cyclisation of 1,4-naphthoquinone and 9,10-phenanthraquinone with alkyne: facile access to 1,8-dioxapyrenes and 1,12-dioxaperylenes as orange and red-emitting luminophores

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