Copper-Catalyzed Borylative Cyclization of o-(Cyano)phenyl Propargyl Carbonates: Synthesis of Functionalized 1-Naphthylamines.

Copper-catalyzed borylative cyclization of o-(cyano)phenyl propargyl carbonates leads to a highly efficient and regioselective synthesis of 3-boryl-1-naphthylamines. A cascade sequence involving the formation of allenyl boronates via borylcupration, deborylation, borylcupration, and cyclization is proposed for this reaction. The resulting products have been applied for the synthesis of a variety of functionalized 1-naphthylamines via oxidation or metal-catalyzed coupling reactions.