Facile approaches toward the synthesis of 6H-isoindolo[2,1-α]indol-6-ones via palladium-catalyzed carbonylation with carbon monoxide

Han, Qingshuai; Fu, Shurong; Zhang, Xiaofeng; Lin, Shen; Huang, Qiufeng

doi:10.1016/j.tetlet.2016.07.108

Cited by 19 publications

(23 citation statements)

References 35 publications

(3 reference statements)

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“…As presented in Fig. 4, the control sample actually exhibited higher conversions (91% for CH 4 and CO 2 ) than ultrasound-assisted samples. Even though the concentration of Pd on the surface remains approximately the same, it was noted that, during ultrasonic treatment, water in the ultrasonic bath became warmer.…”

Section: Ion Exchange (Ie)mentioning

confidence: 79%

“…Even though the concentration of Pd on the surface remains approximately the same, it was noted that, during ultrasonic treatment, water in the ultrasonic bath became warmer. In consequence, Pd(NO 3 ) 2 becomes more soluble and smaller particles are produced; therefore they are more likely to create agglomerates during the IE process, resulting in a decrease of catalytic activity (~70% conversion for CH 4 and CO 2 ) possibly due to lower Pd dispersion than the control. However, despite this reduction in activity, ultrasound significantly accelerates the IE process from 3 days to 3 h; hence with careful optimisation of time and temperature, ultrasound-assisted IE can become a beneficial tool for future use/applications with significant time-consuming benefits.…”

Section: Ion Exchange (Ie)mentioning

confidence: 99%

“…Methane (CH 4 ), a principal component of natural gas, is an abundant hydrocarbon resource that is employed as a relatively inexpensive and clean-burning fuel [1,2]. It is also used in the dry reforming of methane (DRM) to produce synthesis gas (carbon monoxide and hydrogen), a key intermediate in the chemical industry in the preparation of higher hydrocarbons, alcohols and aldehydes [3].…”

Section: Introductionmentioning

confidence: 99%

“…Besides many potential applications of H 2 in different fields, the produced CO can be used in e.g. carbonylation reactions of organic compounds [4][5][6][7] summarised in a review by Veige et al [8] Due to the high thermal stability of CH 4 and CO 2 , the DRM reaction is highly endothermic (Eq. 1), and needs an external energy source, usually high temperatures [1,9].…”

Section: Introductionmentioning

confidence: 99%

“…DRM is typically carried out over supported noble metal catalysts to reduce the activation energy and enhance the reaction at lower temperatures [10]. Nevertheless, the key step during the process is the activation of CH 4 , which occurs on the surface of the active metal; thus the distribution of metal throughout the catalytic support plays a significant role. Recent studies have focused on the preparation…”

Section: Introductionmentioning

confidence: 99%

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Can Ultrasound or pH Influence Pd Distribution on the Surface of HAP to Improve Its Catalytic Properties in the Dry Reforming of Methane?

et al. 2017

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samples were evaluated for their catalytic activity towards dry reforming of methane (DRM) and the reaction was monitored via a thermal conductivity detector, coupled with gas chromatography (GC-TCD). It was found that ultrasound-assisted IE significantly accelerated the process from 3 days to 3 h and with the Pd 0 metal remaining highly distributed upon the HAP with minor changes in catalytic conversions. Moreover, the ultrasound-assisted IW method successfully improved the Pd 0 distribution and catalytic performance. On the other hand, the dispersion of the metal was unaffected after pH treatments in IE with no catalytic improvements observed, in contrast to IW, where considerable increase in metal distribution and subsequently catalytic performance was observed.Abstract The influence of ultrasound and different pH pre-treatments during the metal doping/modification of a hydroxyapatite (HAP) support is investigated. HAP is first synthesised via a hard-template synthetic route using carbon nanorods followed by their full physiochemical characterisation. The HAP was found to be crystalline and comprised a mesoporous structure as observed via XRD and nitrogen adsorption with a BET surface area of 97.57 (±1.16) m 2 g −1. Ultrasound-assisted ion exchange (IE) and incipient wetness impregnation (IW) methodologies were employed to decorate the surface of HAP with Pd 0 and are compared to previous procedures. The influence of pH upon the distribution of Pd 0 throughout the samples during the doping process is also studied. All the prepared Electronic supplementary material The online version of this article

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Section: Ion Exchange (Ie)mentioning

confidence: 79%

Section: Ion Exchange (Ie)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Can Ultrasound or pH Influence Pd Distribution on the Surface of HAP to Improve Its Catalytic Properties in the Dry Reforming of Methane?

et al. 2017

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Intramolecular Carbonylative C–H Functionalization of 1,2,3‐ Triazoles for the Synthesis of Triazolo[1,5‐a]indolones

et al. 2017

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This study presents a synthesis of 4H-[1,2,3]triazolo[1,5-a]indol-4-ones. The key step in the synthesis of this new heterocyclic scaffold is an intramolecular cyclization via an unprecedented carbonylative C-H functionalization of 1-(2-bromoaryl)-1,2,3-triazoles. Isotopic labeling of the carbonyl carbon atom is possible using near stoichiometric amounts of 13 CO. Additionally, an alternative pathway via carbonylative Sonogashira coupling followed by a two-step one pot azidation/cycloaddition is also investigated, giving rise to the same scaffold.

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Steering Site‐Selectivity in Transition Metal‐Catalyzed C−H Bond Functionalization: the Challenge of Benzanilides

Gramage‐Doria

2020

Chemistry A European J

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SelectiveC ÀHb ond functionalization catalyzed by metal complexes have completely revolutionized the wayi n which chemical synthesis is conceived nowadays. Typically, the reactivityo fat ransitionm etal catalyst is the key to control the site-, regio-and/or stereo-selectivity of aC ÀHb ond functionalization. Of particulari nterests are molecules that contain multiple CÀHb onds prone to undergo CÀHb ond activations with very similar bond dissociation energies at different positions. This is the case of benzanilides, relevant chemical motifs that are found in many useful fine chemicals, in which two CÀHs ites are present in chemically different aromatic fragments. In the last years, it has been found that depending on the metal catalyst and the reaction conditions, the amide motif might behave as ad irecting group towardst he metal-catalyzed CÀHb ond activation in the benzamide site or in the anilides ite. The impact and the consequences of such subtle control of site-selectivity are herein reviewed with important applicationsi ncarboncarbon and carbon-heteroatomb ond forming processes. The mechanisms unraveling these unique transformations are discussed in order to provide ab etter understanding for future developmentsi nt he field of site-selective CÀHb ond functionalization with transition metal catalysts.

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Facile approaches toward the synthesis of 6H-isoindolo[2,1-α]indol-6-ones via palladium-catalyzed carbonylation with carbon monoxide

Cited by 19 publications

References 35 publications

Can Ultrasound or pH Influence Pd Distribution on the Surface of HAP to Improve Its Catalytic Properties in the Dry Reforming of Methane?

Can Ultrasound or pH Influence Pd Distribution on the Surface of HAP to Improve Its Catalytic Properties in the Dry Reforming of Methane?

Intramolecular Carbonylative C–H Functionalization of 1,2,3‐ Triazoles for the Synthesis of Triazolo[1,5‐a]indolones

Steering Site‐Selectivity in Transition Metal‐Catalyzed C−H Bond Functionalization: the Challenge of Benzanilides

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