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Successive Pd‐Catalyzed Decarboxylative Cross‐Couplings for the Modular Synthesis of Non‐Symmetric Di‐Aryl‐Substituted Thiophenes
Author(s) -
Messina Cynthia,
Douglas Liam Z.,
Liu Jiang Tian,
Forgione Pat
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000780
Subject(s) - chemistry , aryl , combinatorial chemistry , thiophene , catalysis , palladium , organic synthesis , molecule , coupling reaction , computational chemistry , organic chemistry , alkyl
Oligothiophenes are important organic molecules in a number of burgeoning industries as semi‐conducting materials due to their extensive π‐conjugation and charge transport properties. Typically, non‐symmetric, di‐aryl‐substituted thiophenes are prepared by the successive formation of Grignards, organotin, and/or boronic acid intermediates that can be subsequently employed in cross‐coupling reactions. While reliable, these approaches present synthetic difficulties due to the reactivity of organo‐metallic/pseudo‐metallic species, and produce considerable amounts of waste due to necessary pre‐functionalization. We have developed a decarboxylative cross‐coupling route as an effective strategy for the modular and less wasteful synthesis of a wide range of non‐symmetric, di‐arylthiophenes. This method uses a thiophene ester building block for successive decarboxylative palladium‐catalyzed couplings that allows for the efficient synthesis and evaluation of the opto‐electronic properties of a library of candidate semi‐conductors with functional groups that could be challenging to access using previous routes.