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Synthesis 2017; 49(06): 1285-1294
DOI: 10.1055/s-0036-1588094
DOI: 10.1055/s-0036-1588094
paper
A Step-Efficient Pathway to Chlorine-Functionalized Thiophene Oligomers by Palladium-Catalyzed Deprotonative Coupling of Chlorothiophenes
Further Information
Publication History
Received: 13 September 2016
Accepted after revision: 21 October 2016
Publication Date:
23 November 2016 (online)
Dedicated to Professor Tamejiro Hiyama on the occasion of his 70th birthday
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 head-to-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.
Key words
thiophene oligomer - palladium catalyst - chlorothiophene - Knochel–Hauser base - alternating copolymerSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588094.
- Supporting Information
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See also:
PEPPSI: Pyridine-enhanced precatalyst preparation stabilization and initiation. See: