Herein, we introduce an electrochemical dehydrogenative [3 + 2]/[5 + 2] annulation of easily available -arylacrylamides with γ,σ-unsaturated malonates through C(sp)-H/C(sp)-H functionalization. The employment of inexpensive ferrocene as the redox catalyst allows access to diverse benzo[]azepin-2-ones in moderate to excellent yields without stoichiometric oxidants. This protocol features broad substrate scope and excellent selectivity, and mechanistic studies indicated that the reaction proceeded through the oxidation of a C(sp)-H bond to generate an alkyl radical, radical addition across the C═C bond, [3 + 2]/[5 + 2] annulations, and C(sp)-H functionalization cascades.
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http://dx.doi.org/10.1021/acs.orglett.4c02163 | DOI Listing |
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