Abstract
Azepines and their saturated azepane counterparts are important moieties in bioactive molecules but are underrepresented in current drug screening libraries. Herein, we report a mild and efficient azepine formation via silver-catalyzed dearomative nitrene transfer. A 2,2,2-trichloroethoxysulfonyl (Tces)-protected carbamimidate nitrene precursor, coupled with the appropriate ligand for silver, is essential for achieving the unexpected chemoselectivity between arene dearomatization and benzylic C(sp3)–H amination. Potential applications in the late-stage diversification of azepines to complex molecular scaffolds and diastereoselective hydrogenations to high Fsp3 azepanes are also highlighted.
Supplementary materials
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Supplementary Information
Description
SI including procedures, characterization and spectra for all new compounds.
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