Preparation of substituted triphenylenes via nickel-mediated Yamamoto coupling
Zachary W Schroeder1, Joshua LeDrew1, Vanessa M Selmani1
1Department of Chemistry & Biochemistry, Wilfrid Laurier University Waterloo Ontario N2L 3C5 Canada kmaly@wlu.ca.
Abstract:
Substituted triphenylenes show promise as organic semiconductors because of their ability to form columnar liquid crystalline phases featuring extended π-stacked arrays. While there are several methods for preparing triphenylenes, including oxidative cyclization reactions such as the Scholl reaction, as well as transition metal-catalyzed aryne cyclotrimerization, these methods are not effective for electron deficient triphenylenes. Here we demonstrate that the nickel-mediated Yamamoto coupling of o-dibromoarenes is a concise and efficient way to prepare substituted triphenylenes, including electron-deficient systems that are otherwise challenging to prepare. We also demonstrate the application of this approach to prepare electron deficient discotic mesogens composed of triphenylenes bearing imide and thioimide groups.
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