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