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π-Extended Polyaromatic Hydrocarbons by Sustainable Alkyne Annulations through Double C−H/N−H Activation |
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| Authors: | Dr Elżbieta Gońka Long Yang Ralf Steinbock Dr Fabio Pesciaioli Dr Rositha Kuniyil Prof Dr Lutz Ackermann |
| Institution: | 1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany;2. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
These authors contributed equally to this work. |
| Abstract: | The widespread applications of substituted diketopyrrolopyrroles (DPPs) call for the development of efficient methods for their modular assembly. Herein, we present a π-expansion strategy for polyaromatic hydrocarbons (PAHs) by C−H activation in a sustainable fashion. Thus, twofold C−H/N-H activations were accomplished by versatile ruthenium(II)carboxylate catalysis, providing step-economical access to diversely decorated fluorogenic DPPs that was merged with late-stage palladium-catalyzed C−H arylation on the thus-assembled DPP motif. |
| Keywords: | annulation C−H activation diketopyrrolopyrroles polyaromatic hydrocarbons ruthenium |