Ring-Opening Polymerization of l-Lactide Efficiently Triggered by an Amido-Indole. X-ray Structure of a Complex between l-Lactide and the Hydrogen-Bonding Organocatalyst

N-(3,5-Bis(trifluoromethyl)phenyl)-1H-indole-2-carboxamide 1e is an efficient hydrogen-bonding organocatalyst for the ring-opening polymerization of l-lactide. This new catalytic species does control the dispersity (1.08) and molecular weight (3460 g/mol vs 3064 in theory) of the poly(l-lactides) pr...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2009-10, Vol.131 (42), p.15088-15089
Main Authors: Koeller, Sylvain, Kadota, Joji, Deffieux, Alain, Peruch, Frédéric, Massip, Stéphane, Léger, Jean-Michel, Desvergne, Jean-Pierre, Bibal, Brigitte
Format: Article
Language:English
Subjects:
Amides - chemistry
Catalysis
Chemical Sciences
Crystallography, X-Ray
Dioxanes - chemistry
Hydrogen Bonding
Indoles - chemistry
Models, Molecular
Molecular Structure
Polymers
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Summary:N-(3,5-Bis(trifluoromethyl)phenyl)-1H-indole-2-carboxamide 1e is an efficient hydrogen-bonding organocatalyst for the ring-opening polymerization of l-lactide. This new catalytic species does control the dispersity (1.08) and molecular weight (3460 g/mol vs 3064 in theory) of the poly(l-lactides) prepared in 2 h. 1H NMR analysis showed that compound 1e complexes l-lactide in CDCl3 through the two available NH groups (amide and indole). In particular, the catalytic species appeared to be mainly the H-bonding donor amide (1e in extended conformation, alone or dimer (1e)2) and, to a lesser extend, the dual H-bonding amido-indole (1e in its the pinched conformation). The first X-ray structure of the complex between a H-bonding organocatalyst and l-lactide also revealed a tight H-bonded network between the dimer (1e)2 and l-lactide.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja906119t