Palladium-catalysed regioselective [4 + 2] annulation to access silatetralin-1-amines

Abstract

A palladium-catalysed [4 + 2] annulation of benzosilacyclobutenes with N-allenamides for the synthesis of silatetralin-1-amines is reported. This protocol utilizes N-allenamides as versatile bifunctional reagents, acting as both two-carbon synthons and nitrogen donors. The reaction provides efficient access to structurally diverse silatetralin-1-amines in good yields with high functional group compatibility. Notably, the transformation is characterized by exclusive proximal CC bond insertion with regioselective Si–C(sp²) bond cleavage of benzosilacyclobutenes.