Ag-Catalyzed Annulation of <i>o</i>-Alkynylaryl Aldehydes, Amines, and Diazo Compounds: Construction of Trifluoromethyl- and Cyano-Functionalized Benzo[<i>d</i>]azepines
Sanoop P. Chandrasekharan, Anamika Dhami, Kishor Mohanan
Abstract
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.
Topics & Concepts
ChemistryAnnulationAzepineTrifluoromethylDiazoCatalysisRing (chemistry)ExpansiveCombinatorial chemistryMedicinal chemistryOrganic chemistryAlkylCompressive strengthMaterials scienceComposite materialCyclopropane Reaction MechanismsFluorine in Organic ChemistryCatalytic C–H Functionalization Methods