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Synthesis 2015; 47(19): 3049-3060
DOI: 10.1055/s-0034-1380211
DOI: 10.1055/s-0034-1380211
paper
Selective Friedel–Crafts Acylation Reactions of 2-Arylphenoxyacetic Acids: A Simple and Efficient Methodology to Synthesize Dibenzoxepine and Arylcoumaranone Derivatives
Authors
Further Information
Publication History
Received: 10 March 2015
Accepted after revision: 17 April 2015
Publication Date:
19 June 2015 (online)
Abstract
Intramolecular Friedel–Crafts acylation reactions of 2-arylphenoxyacetic acids are accomplished using trifluoroacetic anhydride or trifluoromethanesulfonic acid at 0 °C or room temperature. Depending on the reaction conditions, dibenzoxepines or arylcoumaranones are obtained in good yields and with high selectivities (83–100%). Plausible mechanistic pathways for the selective formation of the different reaction products are discussed.
Key words
Friedel–Crafts acylations - 2-arylphenoxyacetic acids - dibenzoxepines - arylcoumaranones - regioselectivitySupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380211.
- Supporting Information (PDF)
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