Murahashi Coupling Polymerization: Nickel(II)–N-Heterocyclic Carbene Complex-Catalyzed Polycondensation of Organolithium Species of (Hetero)arenes

Revisiting Murahashi coupling, we found that it effectively allows polymerization of lithiated (hetero)arenes by nickel(II)-catalyzed polycondensation. Deprotonative polymerization of 2-chloro-3-substituted thiophene with n-butyllithium gave head-to-tail-type poly(3-substituted thiophene). Poly(1,4-...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2013-08, Vol.135 (33), p.12208-12211
Main Authors: Fuji, Kanta, Tamba, Shunsuke, Shono, Keisuke, Sugie, Atsushi, Mori, Atsunori
Format: Article
Language:English
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Summary:Revisiting Murahashi coupling, we found that it effectively allows polymerization of lithiated (hetero)arenes by nickel(II)-catalyzed polycondensation. Deprotonative polymerization of 2-chloro-3-substituted thiophene with n-butyllithium gave head-to-tail-type poly(3-substituted thiophene). Poly(1,4-arylene)s were obtained by the reaction of the corresponding dibromides through lithium–bromine exchange. A lithiated thiophene derivative obtained via deprotonative halogen dance also underwent polymerization to afford a bromo-substituted polythiophene.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja406374t