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