title: A general method for the synthesis of 3,5-diarylcyclopentenones via friedel-crafts acylation of vinyl chlorides.
abstract: 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.
authors.affiliation: Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., Rahway, New Jersey 07065, USA. yingju_xu@merck.com
authors.forename: Yingju
authors.initials: Y
authors.lastname: Xu
authors.forename: Mark
authors.initials: M
authors.lastname: McLaughlin
authors.forename: Cheng-yi
authors.initials: CY
authors.lastname: Chen
authors.forename: Robert A
authors.initials: RA
authors.lastname: Reamer
authors.forename: Peter G
authors.initials: PG
authors.lastname: Dormer
authors.forename: Ian W
authors.initials: IW
authors.lastname: Davies
mesh_terms: D000215:Acylation; D003500:Cyclization; D015394:Molecular Structure; D010422:Pentanones / Q000138:chemical synthesis* / Q000737:chemistry*; D014752:Vinyl Chloride / Q000737:chemistry*
chemical_list: D010422:Pentanones; C057461:1-pentene-3-one; D014752:Vinyl Chloride