A Step-Efficient Pathway to Chlorine-Functionalized Thiophene Oligomers by Palladium-Catalyzed Deprotonative Coupling of Chlorothiophenes
SYNTHESIS-STUTTGART(2017)
Abstract
Deprotonative metalation of 2-chloro-3-substituted thiophene at the 5-position of the thiophene ring is performed by using a bulky magnesium amide 2,2,6,6-tetramethylpiperidin-1-yl magnesium chloride lithium chloride salt (TMPMgCl.LiCl). The obtained metallic species reacts with bromothiophene to afford the regioregular headto- tail-type chlorobithiophene, which is subjected to further end functionalization by the coupling reaction with the C-Cl bond. Deprotonative C-H coupling polycondensation of substituted chlorobithiophene derivatives gives polythiophene as a formal alternating copolymer.
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Key words
thiophene oligomer,palladium catalyst,chlorothiophene,Knochel-Hauser base,alternating copolymer
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