1162000-19-2Relevant academic research and scientific papers
A general method for the synthesis of 3,5-diarylcyclopentenones via Friedel-Crafts acylation of vinyl chlorides
Xu, Yingju,McLaughlin, Mark,Chen, Cheng-Yi,Reamer, Robert A.,Dormer, Peter G.,Davies, Ian W.
supporting information; experimental part, p. 5100 - 5103 (2009/10/17)
(Chemical Equation Presented) 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 AlCl3. 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.
