Preparation of substituted triphenylenes via nickel-mediated Yamamoto coupling?

RSC Advances Pub Date: 2021-12-13 DOI: 10.1039/D1RA07931J

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.

Graphical abstract: Preparation of substituted triphenylenes via nickel-mediated Yamamoto coupling
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