NDLI: (Thio)Amidoindoles and (Thio)Amidobenzimidazoles: An Investigation of Their Hydrogen-Bonding and Organocatalytic Properties in the Ring-Opening Polymerization of Lactide

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(Thio)Amidoindoles and (Thio)Amidobenzimidazoles: An Investigation of Their Hydrogen-Bonding and Organocatalytic Properties in the Ring-Opening Polymerization of Lactide

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Pinaud, Noël Bibal, Brigitte Deffieux, Alain Massip, Stéphane Peruch, Frédéric Kadota, Joji Koeller, Sylvain Léger, Jean-michel Desvergne, Jean-pierre Pianet, Isabelle
Description	Author Affiliation: Koeller S ( Institut des Sciences Moléculaires UMR CNRS 5255, Université de Bordeaux, 351 cours de la Libération, 33405 Talence, France.)
Abstract	The mechanism of the ring-opening polymerization (ROP) of lactide catalyzed by two partner hydrogen-bonding organocatalysts was explored. New amidoindoles 4 a,c, thioamidoindoles 4 b,d, amidobenzimidazoles 5 a,c, and thioamidobenzimidazoles 5 b,c were synthesized and used as activators of the monomer. In the solid state and in solution, compounds 4 and 5 showed a propensity for self-association, which was evaluated. (Thio)Amides 4 and 5 do catalyze the ROP of lactide in the presence of a cocatalyst, tertiary amine 3 a or 3 b, which activates the growing polymer chain through hydrogen-bonding. Reactions were conducted in 2–24 h at 20 °C; conversion yields ranged between 22 and 100 %. A detailed study of the intermolecular interactions undertaken between the participating species showed that, as expected, simultaneous weak hydrogen bonds do exist to activate the reagents. Moreover, interactions have been revealed between the partner catalysts 4/5+3. ROP catalyzed by these partner activators is thus governed by multiple dynamic equilibria. The latter should be judiciously adjusted to fine-tune the catalytic properties of (thio)amides and organocatalysts, more generally.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	14
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-04-12
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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