A Step-Efficient Pathway to Chlorine-Functionalized Thiophene Oligomers by Palladium-Catalyzed Deprotonative Coupling of Chlorothiophenes

• Fujita, Keisuke

• Nakagawa, Naoki

• Sunahara, Kazuhiro

• Ogura, Tadayuki

• Okano, Kentaro

• Mori, Atsunori

Abstract

Deprotonative metalation of 2-chloro-3-substituted thiophene at the 5-position of the thiophene ring is performed by 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 C-Cl bond. Deprotonative C-H coupling polycondensation of differently-substituted chlorobithiophene gives polythiophene of the formal alternating copolymer.

Journal

• Synthesis-Stuttgart

  Synthesis-Stuttgart 49 (6), 1285-1294, 2017-03

  Georg Thieme Verlag

Keywords

• thiophene oligomer
• palladium catalyst
• chlorothiophene
• Knochel-Hauser base
• alternating copolymer

Details

• CRID: 1050856995324252544
• NII Article ID: 120006220755
• ISSN: 1437210X
• ISSN: 00397881
• HANDLE: 20.500.14094/90003958
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • CiNii Articles