Beilstein J. Org. Chem.2022,18, 956–962, doi:10.3762/bjoc.18.95
Naoki Kise Toshihiko Sakurai Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101, Koyama-cho Minami, Tottori 680-8552, Japan 10.3762/bjoc.18.95 Abstract The electroreductive coupling of 2-acylbenzoates with acrylonitrile in the presence of TMSCl
and successive treatment with 1 M HCl gave 2-cyanonaphthalen-1-ols or 3-(3-cyanoethyl)phthalides. On the other hand, the reaction of 2-acylbenzoates with methyl vinyl ketone under the same conditions produced 3-(3-oxobutyl)phthalides as the sole products. What determines the product selectivity was
studied using DFT calculations.
Keywords: 2-acylbenzoates; chlorotrimethylsilane; 3-(3-cyanoethyl)phthalides; 2-cyanonaphthalen-1-ols; electroductive coupling; Introduction
The electroreductive coupling between carbon–heteroatom and carbon–carbon double bonds is one of the promising methods for carbon
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Graphical Abstract
Scheme 1:
Electroreductive coupling of phthalic anhydrides with α,β-unsaturated carbonyl compounds and subseq...