Nickel(II)-Catalyzed Cross-Coupling Polycondensation of Thiophenes via C–S Bond Cleavage

Cross-coupling polycondensation of thiophene derivatives occurs via C–S bond cleavage in the presence of a nickel catalyst. Head to tail type (HT) regioregular poly(3-hexylthiophene) is obtained by a nickel(II)-catalyzed deprotonative C–H functionalization polycondensation of 2-(phenylsulfonyl)-3-he...

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Bibliographic Details
Published in:Organometallics 2014-01, Vol.33 (1), p.12-15
Main Authors: Tamba, Shunsuke, Fuji, Kanta, Nakamura, Karin, Mori, Atsunori
Format: Article
Language:English
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Summary:Cross-coupling polycondensation of thiophene derivatives occurs via C–S bond cleavage in the presence of a nickel catalyst. Head to tail type (HT) regioregular poly(3-hexylthiophene) is obtained by a nickel(II)-catalyzed deprotonative C–H functionalization polycondensation of 2-(phenylsulfonyl)-3-hexylthiophene with stoichiometric TMPMgCl·LiCl or with the catalytic secondary amine/RMgX. Debrominative Grignard metathesis (GRIM) polymerization with 5-bromo-2-(phenylsulfonyl)-3-hexylthiophene also proceeds by the catalysis of the nickel(II) complex to afford the corresponding polythiophene.
ISSN:0276-7333
1520-6041
DOI:10.1021/om4010737