Heterogeneous Suzuki and copper-free Sonogashira cross-coupling reactions catalyzed by a reusable palladium(II) complex in water medium

Mondal, Paramita; Roy, Anupam Singha; Mondal, Swastik; Hossain, Dildar

doi:10.1016/j.tetlet.2010.02.079

Cited by 118 publications

(37 citation statements)

References 47 publications

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“…The results are in agreement with the past reports showing that aryl halides containing electron-withdrawing groups are more reactive than aryl halides containing electron-donating groups in Sonogashira coupling reactions. [25][26][27] In addition, it was observed that there was no considerable difference in yields between para-substituted and meta-substituted halogenated aromatic acids ( Table 2, entry 3 vs. 1 and 4 vs. 2).…”

Section: Resultsmentioning

confidence: 89%

Protecting-group-free synthesis of carboxylic group substituted alkynes by Sonogashira coupling in neat water

Zhu¹,

Wang²,

Bai³

et al. 2011

Arkivoc

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An effective, economic and green synthesis of carboxylic group substituted alkynes by Sonogashira coupling of halogenated aromatic acids with phenylacetylene has been developed. The coupling reaction proceeds well using Pd(OAc)2/TPPTS-CuI as catalyst with K2CO3 as base in water. It is worth noting that this procedure avoids the protection/deprotection steps of carboxylic group and obtains the title compounds in good to excellent yields.

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Section: Resultsmentioning

confidence: 89%

Protecting-group-free synthesis of carboxylic group substituted alkynes by Sonogashira coupling in neat water

Zhu¹,

Wang²,

Bai³

et al. 2011

Arkivoc

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“…Some recent examples are shown in Figure 2. Separation of the polymer by filtration and reuse of the catalysts have been achieved for iminopyridine (7) [59] and -dipyridine (8) ligands, [60] aryldiazo-(9) [61] or oxime-derived palladacycles (10) (Figure 2). [62] N-heterocyclic carbenes have become very popular and useful ligands in catalysis including cross-coupling reactions.…”

Section: Polystyrene-supported Ligands For Filtration Recoverymentioning

confidence: 99%

Polymers for Green C–C Couplings

Albéniz

Carrera

2011

Eur J Inorg Chem

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Cleaner and environmentally more friendly cross-coupling reactions can be carried out by the use of polymers as supports. A lot of work has been devoted to attach palladium catalysts on polymers, so they can be easily separated from the reaction mixture and reused. An overview of the methods used for this purpose is given; they include the encapsulation of palladium complexes or palladium nanoparticles by polymers and the synthesis of polymeric ligands that coordinate to palladium. Polymer-supported reagents are also important

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“…Our continuing interest in palladium-catalyzed organic transformations [35][36][37][38] prompted us to extend our attention to the palladium catalyzed Heck reaction. Herein we have reported an efficient procedure for a heterogeneous phosphine-free Heck cross-coupling reaction of aryl halides with terminal alkenes using PS-[(C 6 H 4 CH=N)Pd(OAc)] 2 as the catalyst and K 2 CO 3 as the base.…”

Section: Introductionmentioning

confidence: 99%

Heterogeneously catalyzed phosphine-free heck cross-coupling reaction of aryl halides with reusable palladium(II) schiff base complex

Islam¹,

Mondal²,

Tuhina³

et al. 2011

J. Braz. Chem. Soc.

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O acoplamento entre haletos de arila e terminais alceno (reação de Heck) foi investigado na presença de catalisadores de paládio (II) suportados em poliestirenos contendo bases de Schiff. O catalisador é estável frente ao ar e umidade, e tem atividade catalítica significativa nas reações de acoplamento cruzado de Heck sob condições normais. Vários haletos de arila e alcenos terminais foram facilmente acoplados na presença de ar, fornecendo os correspondentes produtos de acoplamaneto cruzado, em ótimos rendimentos. O catalisador é facilmente recuperado quantitativamente por filtração simples e reutilizado por até sete ciclos sem perda de atividade.The coupling between aryl halides with terminal alkenes (Heck reaction) has been investigated in the presence of a polystyrene-supported Schiff base palladium(II) catalyst. The present catalyst is air and moisture-stable and has significant catalytic activity in Heck cross-coupling reactions under operating conditions. Various aryl halides and terminal alkenes were coupled smoothly under air, to afford the corresponding cross-coupled products in excellent yields. Furthermore, the catalyst can be easily recovered quantitatively by simple filtration and reused up to seven cycles without losing its activity.

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Heterogeneous Suzuki and copper-free Sonogashira cross-coupling reactions catalyzed by a reusable palladium(II) complex in water medium

Cited by 118 publications

References 47 publications

Protecting-group-free synthesis of carboxylic group substituted alkynes by Sonogashira coupling in neat water

Protecting-group-free synthesis of carboxylic group substituted alkynes by Sonogashira coupling in neat water

Polymers for Green C–C Couplings

Heterogeneously catalyzed phosphine-free heck cross-coupling reaction of aryl halides with reusable palladium(II) schiff base complex

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