Recoverable and recyclable chiral organic catalysts

Benaglia, Maurizio

doi:10.1039/b610416a

Cited by 121 publications

(23 citation statements)

References 52 publications

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“…4 Polymers of discreet solubility can be extremely convenient because they allow us to realize a ''monophase'' (that is, homogeneous) catalysis while still enjoying the advantage of biphase separations. 5,6 We have recently turned our attention to polymethylhydrosiloxane (PMHS) that presents several positive features such as low cost, commercial availability, easy fuctionalization, and very favourable solubility profile. Indeed, PMHS is soluble in many organic solvents and insoluble in a few other solvents, like hexanes, thus allowing us to run a catalyzed reaction under homogeneous conditions and to isolate and recover the catalyst as if it were bound to an insoluble polymer.…”

mentioning

confidence: 99%

Poly(methylhydrosiloxane)-supported chiral imidazolinones: new versatile, highly efficient and recyclable organocatalysts for stereoselective Diels–Alder cycloaddition reactions

2012

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confidence: 99%

Poly(methylhydrosiloxane)-supported chiral imidazolinones: new versatile, highly efficient and recyclable organocatalysts for stereoselective Diels–Alder cycloaddition reactions

2012

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“…The conceptualization of organocatalysis that followed the ground‐breaking works of List, Lerner and Barbas on enamine catalysis and MacMillan on iminium ion catalysis paved the way for the extension of these simple (yet hitherto elusive) concepts to hundreds of related reactions . This fever also arrived to the main players in the field of solid‐supported catalysts, allured by the fact that these species would not suffer the problem of metal leaching –…”

Section: Precedents and Practical Considerationsmentioning

confidence: 99%

Catalytic Enantioselective Flow Processes with Solid‐Supported Chiral Catalysts

Rodríguez‐Escrich

Pericàs

2018

The Chemical Record

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Sustainability concerns are the wind in the sails for the development of novel, more selective catalytic processes. Hence, chiral catalysts play a crucial role in the green production of enantioenriched compounds. To further increase the green profile of this approach, the use of solid-supported catalytic species is appealing due to the reduced generation of waste, as well as the possibility of reusing the precious catalyst. Even more attractive is the implementation of flow processes based on these immobilized catalysts, a flexible strategy that allows to generate from milli- to multi-gram amounts of chiral product with a reduced footprint set-up. Herein, we will present the efforts devoted in our laboratory towards the immobilization of chiral catalysts and their use in single-pass, highly enantioselective, flow processes. Proline, diarylprolinols, other aminocatalysts, squaramides, thioureas, phosphoric acids and even chiral ligands and metal-based catalysts constitute our current toolkit of supported species for enantioselective catalysis.

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“…Since it is known that the properties of the polymeric support playing a crucial role in catalysis [48] are: the swelling capability (Pd-pol swells in water), the porosity (Pd-pol is macroporous) and the mild reticular structure (Pd-pol is not too much cross-linked), we deemed it worthwhile to test Pd-pol as a supported catalyst for the Suzuki reaction in neat water. We found that Pd-pol was active and recyclable: (i) with aryl bromides as substrates without any additive or co-solvent, even using a Pd/substrate molar ratio of 1/10,000; (ii) with aryl chlorides, in the presence of a phase transfer agent.…”

Section: Introductionmentioning

confidence: 99%