One-Pot Dual C–C Bond-Forming Cascade Process via Suzuki Coupling and Intramolecular Cyclocondensation: An Access to Functionalized Naphthalenes

Abstract

Naphthyl ketones encompass a class of essential compounds of biological and industrial significance. The development of synthetic strategies to achieve naphthyl ketones in single-step reactions from readily available materials is highly desirable. Herein, domino one-pot synthesis of functionalized naphthyl ketones via intermolecular Suzuki–Miyaura coupling, followed by intramolecular distal aldol-type condensation with the γ-methyl/methylene groups is reported. The present strategy displayed a comprehensive substrate scope and good functional group tolerance and enabled access to a variety of substituted naphthyl ketones, including aromatic–aliphatic hybrid frameworks of interesting structural features starting from the easily accessible starting materials such as α-iodoenone and 2-formylphenylboronic acids as well as 2-formylphenylboronic acid pinacol esters.