Isocyanate-Free Polyurea Synthesis via Ru-Catalyzed Carbene Insertion into the N-H Bonds of Urea.
Journal
Macromolecules
ISSN: 0024-9297
Titre abrégé: Macromolecules
Pays: United States
ID NLM: 0365316
Informations de publication
Date de publication:
08 Nov 2022
08 Nov 2022
Historique:
received:
14
07
2022
revised:
04
10
2022
entrez:
18
11
2022
pubmed:
19
11
2022
medline:
19
11
2022
Statut:
ppublish
Résumé
Polyureas have widespread applications due to their unique material properties. Because of the toxicity of isocyanates, sustainable isocyanate-free routes to prepare polyureas are a field of active research. Current routes to isocyanate-free polyureas focus on constructing the urea moiety in the final polymerizing step. In this study we present a new isocyanate-free method to produce polyureas by Ru-catalyzed carbene insertion into the N-H bonds of urea itself in combination with a series of bis-diazo compounds as carbene precursors. The mechanism was investigated by kinetics and DFT studies, revealing the rate-determining step to be nucleophilic attack on a Ru-carbene moiety by urea. This study paves the way to use transition-metal-catalyzed reactions in alternative routes to polyureas.
Identifiants
pubmed: 36397938
doi: 10.1021/acs.macromol.2c01457
pmc: PMC9648342
doi:
Types de publication
Journal Article
Langues
eng
Pagination
9690-9696Informations de copyright
© 2022 The Authors. Published by American Chemical Society.
Déclaration de conflit d'intérêts
The authors declare no competing financial interest.
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