Beilstein J. Org. Chem.2022,18, 956–962, doi:10.3762/bjoc.18.95
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
context, we report here that the electroreduction of o-acylbenzoates 1 with acrylonitrile (2a) in the presence of TMSCl and subsequent treatment with 1 M HCl gives 2-cyanonaphthalen-1-ols 3 or 3-(3-cyanoethyl)phthalides 4 (Scheme 3). The product selectivity depends on the position of the methoxy
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Graphical Abstract
Scheme 1:
Electroreductive coupling of phthalic anhydrides with α,β-unsaturated carbonyl compounds and subseq...