Original use of the same heterogeneous chiral catalyst batch to promote different asymmetric reactions

Zulauf, Anaïs; Mellah, Mohamed; Schulz, Emmanuelle

doi:10.1039/b913516b

Cited by 31 publications

(16 citation statements)

References 27 publications

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“…Remarkably, no trace of chloro-stilbene 1, nor other compounds related to 3-chloroiodobenzene, was detected by GC after the 4 th run, highlighting, therefore, the recycling protocol quality. [36] Thus, the desired nitro-stilbene 9 was obtained in excellent yields upon recycling, 70% and 68% for the 4 th and 5 th run, respectively. Interestingly, these yields are very close to the ones obtained with the fresh catalyst (i.e., 76%, see Scheme 3), showing that the catalyst exhibits high stability over these reaction conditions.…”

Section: Resultsmentioning

confidence: 96%

One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

et al. 2010

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Joucla, Lionel Cusati, Giuseppe Pinel, Catherine Djakovitch, LaurentThe synthesis of (E)-stilbenes was performed following a one-pot Suzuki/Heck sequence through the use of potassium vinyltrifluoroborate. The combination of heterogeneous palladium/silica (Pd/SiO2) catalyst with potassium phosphate monohydrate (K3PO4H2O) as base resulted in useful to good isolated yields regardless of the ortho-, meta- or para-substitution of the aryl halides employed. In a sustainable approach. we found that bio-sourced 1,3-propanediol could advantageously replace N-methyl-pyrrolidone (NMP) as similar yields were obtained Moreover, the reactivity gap between aryl iodides and bromides resulting from the use of 1,3-propanediol allowed an efficient multi-component approach toward the synthesis of (E)-stilbenes. Furthermore. this heterogeneous catalyst was found to he extremely robust despite the use of aerobic conditions and was successfully re-used over several cycles

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Section: Resultsmentioning

confidence: 96%

One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

et al. 2010

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“…Nevertheless, it should be noted that the building up of conjugated polymer networks cross-linked by organometallic bridges reviewed in 2005 by Weder [232] accounted for a large panel of electrogenerated structures. Recently, chiral polysalen-thiophene chromium complex was electrosynthesized and used to promote asymmetric reactions [233]; electropolymerization of carbine ended by bithiophene units was reported by Cowley et al [234].…”

Section: Resultsmentioning

confidence: 99%

Electropolymerized Films of π‐Conjugated Polymers. A Tool for Surface Functionalization: A Brief Historical Evolution and Recent Trends

Bidan

2010

Electropolymerization

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“…These electrogenerated polymers were tested as heterogeneous catalysts in an original multi reaction procedure in which the same catalyst batch was engaged in a complete new transformation at each recycling. [37] Co-salen polymers were similarly prepared and the dynamic HKR of epibromohydrin was chosen as test reaction for which Co(III) salts were essential for the substrates activation in a bimetallic manner. Electropolymerization was performed directly starting from Co(II)-salen, the cobalt center being oxidized at a lower potential than the thiophene moiety.…”

Section: Polymerization Of Salen Derivativesmentioning

confidence: 99%

Chiral Salen Complexes for Asymmetric Heterogeneous Catalysis: Recent Examples for Recycling and Cooperativity

2019

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Chiral salen complexes are privileged and versatile catalysts used in a wide variety of enantioselective transformations. Researches for their use in multicatalysis, including cooperative as well as tandem processes, are more recent, but many reports already highlight the important effect of the salen ligand structure on reaction rates and/or selectivities. This review article thus outlines the literature covering last five years, on the current developments of chiral polymetallic salen complexes used in asymmetric heterogeneous catalysis; their preparation, their efficiency as catalysts in various reactions and their recyclability are highlighted according to the immobilization procedures involved for their heterogenization. These methods include grafting on organic or inorganic supports insuring easy recovery by simple filtration. Polymerization processes are also part of recent research, leading to high densities of catalytic sites to favor their cooperativity. Combination of salen complexes via non covalent interactions or their introduction on MOFs and COFs networks is currently in full expansion, with examples of highly functionalized and enantioenriched products issued from tandem catalysis.

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Original use of the same heterogeneous chiral catalyst batch to promote different asymmetric reactions

Abstract: An electrogenerated heterogeneous chiral (poly)salen-thiophene chromium complex successfully promoted different asymmetric catalytic reactions in an original successive manner, demonstrating its high stability and versatility.

Cited by 31 publications

References 27 publications

One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

One‐Pot Suzuki/Heck Sequence for the Synthesis of (E)‐Stilbenes Featuring a Recyclable Silica‐Supported Palladium Catalyst via a Multi‐Component Reaction in 1,3‐Propanediol

Electropolymerized Films of π‐Conjugated Polymers. A Tool for Surface Functionalization: A Brief Historical Evolution and Recent Trends

Chiral Salen Complexes for Asymmetric Heterogeneous Catalysis: Recent Examples for Recycling and Cooperativity

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