Palladium-catalyzed hydroesterification of styrene derivatives in the presence of ionic liquids

Klingshirn, Marc A.; Rogers, Robin D.; Shaughnessy, Kevin H.

doi:10.1016/j.jorganchem.2005.05.031

Cited by 57 publications

(29 citation statements)

References 38 publications

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“…[11,23,25,46,47] It was reported that the insertion of styrene into metal acyl bond led to gem products, while insertion into hydrides led to trans products. [48] Based on the analysis of the literature and the present experimental results, we tentatively proposed two schemes where the hydride mechanism plays represents the major route towards the trans product. This was clear from the promoting effect of a hydride source observed with acid (Table 3).…”

Section: Proposed Mechanismsmentioning

confidence: 77%

Palladium–dppb–borate‐catalyzed regioselective synthesis of cinnamate esters by alkoxycarbonylation of phenylacetylene

Tijani

Suleiman

Ali

2008

Applied Organom Chemis

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The regioselective alkoxycarbonylation of phenylacetylene into various cinnamate esters was achieved with a catalyst system formed from palladium (II), 1,4-bis(diphenylphosphino) butane (dppb) and salicylborate complex in acetonitrile as a solvent. The influence of various parameters on the overall conversion of phenylacetylene and the selectivity of the reaction were studied systematically by varying the type of palladium complex, acids promoter, CO pressure, temperature and the reaction time. This investigation allowed us to obtain the predominant formation of cinnamate esters with excellent selectivity (90-96%).

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Section: Proposed Mechanismsmentioning

confidence: 77%

Palladium–dppb–borate‐catalyzed regioselective synthesis of cinnamate esters by alkoxycarbonylation of phenylacetylene

Tijani

Suleiman

Ali

2008

Applied Organom Chemis

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“…Ionic liquids have been widely exploited in numerous organic reactions due to the versatility in the physical properties such as ease of product separation, [26,27] enhancement in rate of reaction, [28][29][30] catalyst immobilization, [31][32][33] and recyclability. [34][35][36] Modifications in cations and/or anions have facilitated their use in organic reactions while playing a role of reagent, solvent or catalyst.…”

Section: Applications Of Ionic Liquids In Organic Synthesismentioning

confidence: 99%

Safer and Greener Catalysts – Design of High Performance, Biodegradable and Low Toxicity Ionic Liquids

Gore¹,

Gathergood²

2013

Ionic Liquids - New Aspects for the Future

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“…[34] The reaction was first optimized, using [C 4 mim] [NTf 2 ] as the ionic liquid and styrene as the substrate, to determine the best conditions (like CO pressure, ionic liquid:MeOH ratio, temperature). Then, all ionic liquids were tested under these optimized conditions ( Table 2 6 ] ionic liquids.…”

Section: Use Of Ionic Liquids In Alkoxycarbonylation Reactions Of Alkmentioning

confidence: 99%

“…Ionic liquids used by Shaughnessy. [34] www.asc.wiley-vch.de cohols were used as well as addition of several different bidentate phosphines. In the absence of bidentate phosphines, high conversions and moderate to high selectivities towards the branched product (up to 100 % when benzyl alcohol was used) could be achieved.…”

Section: Use Of Ionic Liquids In Alkoxycarbonylation Reactions Of Alkmentioning

confidence: 99%

Multiphase Systems for the Recycling of Alkoxycarbonylation Catalysts

Pater¹,

Deelman²,

Elsevier³

et al. 2006

Adv Synth Catal

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This review evaluates the various multiphasic systems that have been developed for catalyst recycling in the context of alkoxycarbonylation of alkenes and alkynes. Immobilization of the catalyst on an insoluble support, such as silica, alumina, clay or a polymer, as well as immobilization in the inorganic phase of several liquid/liquid biphasic systems (aqueous/organic, ionic liquid/organic, fluorous/organic or supercritical CO 2 /organic) has been described. In several cases detailed information on the efficiency of catalyst separation and recycling is available. Most of the work was focused on the alkoxycarbonylation reactions of alkenes, for which several efficient methods for catalyst recycling were demonstrated. The recycling of catalyst through specific precipitation from supercritical CO 2 or selective dissolution in a fluorous phase, has received only scant attention but offers many opportunities for further improvement.

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Palladium-catalyzed hydroesterification of styrene derivatives in the presence of ionic liquids

Cited by 57 publications

References 38 publications

Palladium–dppb–borate‐catalyzed regioselective synthesis of cinnamate esters by alkoxycarbonylation of phenylacetylene

Palladium–dppb–borate‐catalyzed regioselective synthesis of cinnamate esters by alkoxycarbonylation of phenylacetylene

Safer and Greener Catalysts – Design of High Performance, Biodegradable and Low Toxicity Ionic Liquids

Multiphase Systems for the Recycling of Alkoxycarbonylation Catalysts

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