Ag-Catalyzed Annulation of o-Alkynylaryl Aldehydes, Amines, and Diazo Compounds: Construction of Trifluoromethyl- and Cyano-Functionalized Benzo[d]azepines

A Ag-catalyzed three-component annulation protocol, which uses o-alkynylaryl aldehydes, amines, and trifluorodiazoethane or diazoacetonitrile, to forge a new class of trifluoromethyl- and cyano-functionalized benzo[d]azepine is presented in this Letter. The key transformations involved in this reaction are the transient formation of the isoquinolinium intermediate and the subsequent ring-expansive addition of in situ-formed silver trifluorodiazoethylide to this intermediate. The practicality of this protocol is illustrated by realizing access to a wide range of densely functionalized benzo[d]azepines.