Intermolecular Friedel–Crafts Acylation/Cyclization Reaction of 2‐Methoxybenzoyl Chlorides with 1‐Haloalkynes for the Synthesis of 3‐Halo(thio)Chromenones

ABSTRACT A Lewis acid–promoted intermolecular Friedel–Crafts acylation/cyclization reaction of 2‐methoxybenzoyl chlorides with 1‐haloalkynes has been developed to access various 3‐halo(thio)chromenones. This one‐pot methodology features mild reaction conditions, operational simplicity, and broad substrate scope, tolerating various diversely decorated 1‐haloalkynes and 2‐methoxybenzoyl chlorides. Gram‐scale experiments and late‐stage modifications, including Cu‐catalyzed heterocycle formation and Pd‐catalyzed Suzuki‐Miyaura coupling, further highlight the potential synthetic practicality of this protocol. This work offers a straightforward and versatile approach to synthesize 3‐halo(thio)chromenones.