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Synthesis 2015; 47(19): 3049-3060
DOI: 10.1055/s-0034-1380211
paper
© Georg Thieme Verlag Stuttgart · New York

Selective Friedel–Crafts Acylation Reactions of 2-Arylphenoxyacetic Acids: A Simple and Efficient Methodology to Synthesize Dibenzoxepine and Arylcoumaranone Derivatives

Jialin Wang
a   School of Chemistry and Materials Science, Heilongjiang University, 150080, Harbin, P. R. of China
b   Key Laboratory of Chemical Engineering Process & Technology for High-Efficiency Conversion, College of Heilongjiang Province, 150080, Harbin, P. R. of China   Email: wenyichu@hlju.edu.cn   Email: Sunzz@hlju.edu.cn
,
Jiaqi Liu
a   School of Chemistry and Materials Science, Heilongjiang University, 150080, Harbin, P. R. of China
b   Key Laboratory of Chemical Engineering Process & Technology for High-Efficiency Conversion, College of Heilongjiang Province, 150080, Harbin, P. R. of China   Email: wenyichu@hlju.edu.cn   Email: Sunzz@hlju.edu.cn
,
Hao Lan
a   School of Chemistry and Materials Science, Heilongjiang University, 150080, Harbin, P. R. of China
b   Key Laboratory of Chemical Engineering Process & Technology for High-Efficiency Conversion, College of Heilongjiang Province, 150080, Harbin, P. R. of China   Email: wenyichu@hlju.edu.cn   Email: Sunzz@hlju.edu.cn
,
Wenyi Chu*
a   School of Chemistry and Materials Science, Heilongjiang University, 150080, Harbin, P. R. of China
b   Key Laboratory of Chemical Engineering Process & Technology for High-Efficiency Conversion, College of Heilongjiang Province, 150080, Harbin, P. R. of China   Email: wenyichu@hlju.edu.cn   Email: Sunzz@hlju.edu.cn
,
Zhizhong Sun*
a   School of Chemistry and Materials Science, Heilongjiang University, 150080, Harbin, P. R. of China
b   Key Laboratory of Chemical Engineering Process & Technology for High-Efficiency Conversion, College of Heilongjiang Province, 150080, Harbin, P. R. of China   Email: wenyichu@hlju.edu.cn   Email: Sunzz@hlju.edu.cn
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Publication History

Received: 10 March 2015

Accepted after revision: 17 April 2015

Publication Date:
19 June 2015 (online)

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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 - regioselectivity

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380211.
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