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- Title
Successive Pd‐Catalyzed Decarboxylative Cross‐Couplings for the Modular Synthesis of Non‐Symmetric Di‐Aryl‐Substituted Thiophenes.
- Authors
Messina, Cynthia; Douglas, Liam Z.; Liu, Jiang Tian; Forgione, Pat
- Abstract
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.
- Subjects
BORONIC acids; OLIGOTHIOPHENES; SEMICONDUCTORS; FUNCTIONAL groups; SUSTAINABLE chemistry
- Publication
European Journal of Organic Chemistry, 2020, Vol 2020, Issue 32, p5182
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202000780