ZHANG, Dawei; JARDEL, Damien; PERUCH, Frédéric; CALIN, Nathalie; DUFAUD, Véronique; DUTASTA, Jean-Pierre; MARTINEZ, Alexandre; BIBAL, Brigitte

doi:10.1002/ejoc.201600080

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ZHANG, Dawei
Laboratoire de Chimie - UMR5182 [LC]
Department of Chemistry, East China Normal University, Shanghai [ECNU]

JARDEL, Damien
Institut des Sciences Moléculaires [ISM]

PERUCH, Frédéric

Laboratoire de Chimie des Polymères Organiques [LCPO]
Team 1 LCPO : Polymerization Catalyses & Engineering

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European Journal of Organic Chemistry. 2016, vol. 8, p. 1619-1624

Wiley-VCH Verlag

Résumé en anglais

The hydrogen-bonding activation of C=O bonds by azaphosphatranes was explored in a model reaction, i. e., the ring-opening polymerization of lactide. The polymerization process was controlled, and allowed the preparation of polylactides with narrow dispersity under mild conditions (20 degrees C, 24 h, 10 mol-% catalyst loading). Interestingly, the steric hindrance of azaphosphatranes, as globular rigid structures, prevents any undesired interaction with the tertiary amine cocatalysts, as shown by X-ray analysis and semi-empirical calculations. In contrast to their organocatalytic activity in the CO2/epoxide reaction, all of the phosphonium derivatives tested were found to be efficient catalysts in this ROP benchmark reaction.< Réduire

Mots clés en anglais

Phosphorus

Hydrogen bonds

Organocatalysis

Ring-opening polymerization

Lactide

ASYMMETRIC CATALYSIS

LIVING POLYMERIZATION

ORGANIC-SYNTHESIS

CYCLIC ESTERS

PROAZAPHOSPHATRANES

BASE

CO2

CONVERSION

DONORS

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Azaphosphatranes as Hydrogen-Bonding Organocatalysts for the Activation of Carbonyl Groups: Investigation of Lactide Ring-Opening Polymerization

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