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Copper‐Catalyzed Direct CH Arylation of Thieno[3,4‐ c ]pyrrole‐4,6‐dione (TPD): Toward Efficient and Low‐Cost Synthesis of π‐Functional Small Molecules
Author(s) -
Song YiTing,
Lin PoHan,
Liu ChingYuan
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400524
Subject(s) - chemistry , triazene , catalysis , combinatorial chemistry , pyrrole , copper , amine gas treating , nitrile , aryl , molecule , functional group , coupling reaction , organic chemistry , polymer , alkyl
A series of thieno[3,4‐ c ]pyrrole‐4,6‐dione (TPD)‐based functional small molecules were efficiently synthesized through direct CH 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 CH 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.