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

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)solvent...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2014-12, Vol.356 (18), p.3761-3768
Main Authors: Song, Yi-Ting, Lin, Po-Han, Liu, Ching-Yuan
Format: Article
Language:English
Subjects:
4-c]pyrrole-4
6-dione (TPD)
Chlorides
Copper
direct CH arylation
Esters
Joining
Ligands
Nitriles
Optimization
Synthesis
thieno
thieno[3,4‐c]pyrrole‐4,6‐dione (TPD)
TPD
π-functional small molecules
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Summary: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 π‐functional materials.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201400524