A General Method for the Synthesis of 3,5-Diarylcyclopentenones via Friedel—Crafts Acylation of Vinyl Chlorides

摘要

A general approach for the synthesis of 3,5-diarylcyclopentenones was developed. Key aspects of this approach are the intramolecular Friedel—Crafts-type cyclization of vinyl chlorides and subsequent Pd-catalyzed cross-coupling reactions. The requisite vinyl chloride-bearing arylacetic acid precursors are readily available by straightforward alkylation of arylacetic acid esters and undergo cyclization to yield 3-chloro-5-aryl-2-cyclopentenones when treated with AlCl_3. The vinylogous acid chloride functionality present in these immediate products allows for further elaboration via Pd-catalyzed cross-coupling chemistry, leading to a diverse array of products.