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Bridged benzazepine scaffolds, possessing unique structural and physicochemical activities, are widespread in various natural products and drugs. The construction of these skeletons often requires elaborate synthetic effort with low efficiency. Herein, we develop a simple and divergent approach for constructing various bridged benzazepines by a photocatalytic intermolecular dearomatization of naphthalene derivatives with readily available α‐amino acids. The bridged motif is created via a cascade sequence involving photocatalytic 1,4‐hydroaminoalkylation, alkene isomerization and cyclization. Interestingly, the diastereoselectivity can be regulated through different reaction modes in the cyclization step. Moreover, aminohydroxylation and its further bromination have also been demonstrated to access highly functionalized bridged benzazepines. Preliminary mechanistic studies have been performed to get insights into the mechanism. This method provides a divergent synthetic approach for construction of highly functionalized bridged benzazepines, which have been otherwise difficult to access. [ABSTRACT FROM AUTHOR]

Amides have played a vital role in polymeric materials, natural products and pharmaceuticals. In recent years, transition metal catalyzed C−N bond formation reaction provides a reliable strategy for amides construction. Herein, we disclosed a photo‐induced electrophilic amidation reaction with N‐methoxyamides and arylboronic acids at low temperature using a simple iron salt as the catalyst precursor. Initial mechanistic studies suggested that crucial amide radical species was involved. [ABSTRACT FROM AUTHOR]