Copper-catalyzed direct C-H arylation of thieno[3,4-c]pyrrole-4,6-dione (TPD): Toward efficient and low-cost synthesis of π-functional small molecules

Yi Ting Song, Po Han Lin, Ching Yuan Liu

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

A series of thieno[3,4-c]pyrrole-4,6-dione (TPD)-based functional small molecules were efficiently synthesized through direct C-H arylations using inexpensive copper salts. In this study, we examined all required reaction parameters including various copper complexes, ligands, bases, and (co)-solvents. Under the optimum reaction conditions, the C-H arylation proceeded smoothly and a variety of functional groups such as ester, nitrile, fluoride, chloride, triazene, and amine were tolerated. This method provides a step-economical and relatively low-cost synthetic alternative to presently used coupling reactions for the preparation of TPD-containing p-functional materials.

Original languageEnglish
Pages (from-to)3761-3768
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number18
DOIs
StatePublished - 15 Dec 2014

Keywords

  • Copper
  • Direct C-H arylation
  • Thieno[34-c]pyrrole-46-dione (TPD)
  • TPD
  • π-Functional small molecules

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