A supported palladium nanocatalyst for copper free acyl Sonogashira reactions: One-pot multicomponent synthesis of N-containing heterocycles

Santra, Subhankar; Dhara, Kalyan; Ranjan, Priyadarshi; Bera, Parthasarathi; Mandal, Swadhin K.

doi:10.1039/c1gc15869d

Cited by 67 publications

(33 citation statements)

References 81 publications

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“…Mandal and his group reported the poly‐1,4‐phenylene sulphide (PPS) supported nanoparticles catalysed copper free acyl Sonogashira reaction at moderate temperatures for 12 h. Bakherad et al. reported copper‐ and solvent‐free synthesis of ynones catalysed by polystyrene supported Pd 0 nanoparticles.…”

Section: Resultsmentioning

confidence: 99%

Montmorillonite K‐10‐Supported Palladium Nanoparticles for Copper‐Free Acyl Sonogashira Reaction

et al. 2017

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Preparation of palladium nanoparticles supported on montmorillonite K‐10 clay is described. The utility of thus prepared catalyst was examined for copper free acyl Sonogashira reaction of acid chlorides with phenyl acetylenes to achieve various ynone scaffolds. Coumarin derived ynones were also synthesized under mild optimized reaction conditions. All the title compounds were obtained in good to excellent yield. The recycling efficiency of the catalyst was extremely good and used successfully for seven cycles without significant drop in the yield.

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Section: Resultsmentioning

confidence: 99%

Montmorillonite K‐10‐Supported Palladium Nanoparticles for Copper‐Free Acyl Sonogashira Reaction

et al. 2017

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“…With regard to the mechanistic path for the present transformation, a plausible mechanism would be the formation of palladium(0) species C from precursor A via intermediate B and homocoupling of terminal alkynes (Scheme ). This is followed by the oxidative addition of acid chloride to form intermediate D. Subsequent alkyne coordination results in the formation of acyl palladium complex F via intermediate E. In the final step, the product is obtained by reductive elimination, along with regeneration of the catalyst …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Iron Oxide Palladium Nanoparticles and Their Catalytic Applications for Direct Coupling of Acyl Chlorides with Alkynes

et al. 2016

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A new, magnetic, silica‐based, palladium nanocatalyst has been synthesized and employed for the first time in the direct coupling of acyl chlorides with terminal alkynes to prepare a variety of ynones. The synthesized nanocomposite is an excellent heterogeneous catalyst for copper‐free, phosphine‐free, C−C bond formation through the Sonogashira reaction under aerobic conditions at room temperature without the use of any additives and inert conditions. The synthesized catalyst has been comprehensively characterized by various techniques, such as XRD, SEM, TEM, energy‐dispersive X‐ray spectroscopy, X‐ray photoelectron spectroscopy, inductively coupled plasma, FTIR spectroscopy, vibrating sample magnetometry, and atomic absorption spectroscopy. This nanocatalyst can be magnetically recovered and reused in multiple runs without any noticeable loss in catalytic activity.

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“…The most common methods for the preparation of ynones involve the metal-catalyzed couplings of acyl halides and terminal alkynes (or alkynyl metal) as well as the Pd-catalyzed acyl or carbonylative Sonogashira reactions. [26][27][28] In addition, there are a few metal-free methodologies reporting the oxidation of propargylic alcohols with different oxidation systems. 29 However, the use of molecular iodine is unprecedented.…”

Section: Resultsmentioning

confidence: 99%

Oxidation of alcohols to carbonyl compounds with molecular iodine in the presence of potassium tert-butoxide

Luo¹,

Nan²,

Yu³

et al. 2014

Arkivoc

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An efficient protocol for the oxidation of alcohols to carbonyl compounds with molecular iodine and potassium tert-butoxide is described. Various primary and secondary alcohols were converted to the corresponding aldehydes and ketones in high yields. The oxidation of 2-phenylethanol produced an "abnormal" acetalic ketone. The readily availability of starting materials, convenient synthetic procedure, operational simplicity, mild reaction conditions, and high yields makes this protocol a competitive alternative in the synthesis of ynones and ketones as well as aryl aldehydes.

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A supported palladium nanocatalyst for copper free acyl Sonogashira reactions: One-pot multicomponent synthesis of N-containing heterocycles

Cited by 67 publications

References 81 publications

Montmorillonite K‐10‐Supported Palladium Nanoparticles for Copper‐Free Acyl Sonogashira Reaction

Montmorillonite K‐10‐Supported Palladium Nanoparticles for Copper‐Free Acyl Sonogashira Reaction

Synthesis of Iron Oxide Palladium Nanoparticles and Their Catalytic Applications for Direct Coupling of Acyl Chlorides with Alkynes

Oxidation of alcohols to carbonyl compounds with molecular iodine in the presence of potassium tert-butoxide

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