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One-Pot Synthesis of Dibenzo[b,d]oxepines via Olefinic C–F Bond Functionalization and Intramolecular Pd-Catalyzed C–H Arylation

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posted on 30.10.2018, 00:00 by Elina Ausekle, Peter Ehlers, Alexander Villinger, Peter Langer
We report base-mediated reactions of 1-bromo-2-(2,2-difluorovinyl)­benzenes with phenols followed by Pd-catalyzed intramolecular C–H arylation, which offers a novel route to a pharmaceutically relevant class of compounds, oxepines. Construction of these medium-sized ring structures proceeds as a one-pot two-step reaction through diaryl ketene acetals as intermediates. It allows to obtain various dibenz­[b,d]­oxepine derivatives in moderate to high yields.