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Mild, Efficient Friedel−Crafts Acylations from Carboxylic Acids Using Cyanuric Chloride and AlCl3
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Department of Medicine.
, ‡Departments of Pharmaceutical Sciences and of Chemistry.
Abstract
A mild method for Friedel−Crafts acylation with aromatic and aliphatic carboxylic acids using cyanuric chloride, pyridine, and AlCl3 was developed. Both inter- and intramolecular acylations were achieved at room temperature in high yield and in very short reaction times.
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This article has been cited by 2 ACS Journal articles (2 most recent appear below).
Total Synthesis and Absolute Stereochemical Assignment of Kibdelone C
David L. Sloman , Jeffrey W. Bacon , and John A. PorcoJournal of the American Chemical Society 0 (ja),Total Synthesis and Absolute Stereochemical Assignment of Kibdelone C
David L. Sloman , Jeffrey W. Bacon , and John A. PorcoJournal of the American Chemical Society 0 (ja),The kibdelones are hexacyclic tetrahydroxanthones and potent anticancer agents isolated from an Australian microbe. Herein, we describe the synthesis of a chiral, non-racemic iodocyclohexene carboxylate EF ring fragment of the kibdelones employing an ...
A General Method for the Synthesis of 3,5-Diarylcyclopentenones via Friedel−Crafts Acylation of Vinyl Chlorides
Yingju Xu, Mark McLaughlin, Cheng-yi Chen, Robert A. Reamer, Peter G. Dormer and Ian W. DaviesThe Journal of Organic Chemistry2009 74 (14), 5100-5103A General Method for the Synthesis of 3,5-Diarylcyclopentenones via Friedel−Crafts Acylation of Vinyl Chlorides
Yingju Xu, Mark McLaughlin, Cheng-yi Chen, Robert A. Reamer, Peter G. Dormer and Ian W. DaviesThe Journal of Organic Chemistry2009 74 (14), 5100-5103A 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 ...
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History
- Published In Issue July 03, 2008
- Article ASAPMay 31, 2008
- Received: April 02, 2008
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