Chemoselective silver-catalyzed nitrene transfer: Tunable syntheses of azepines and cyclic carbamimidates

19 June 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

silver
nitrene transfer
chemoselective
aza-Büchner
skeletal editing

Supplementary materials

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SI including procedures, characterization and spectra for all new compounds.
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