Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 6, Pages 2264-2269Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo702414y
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A simple and efficient AlCl3-mediated C-C coupling reaction between readily available alpha-hydroxyketene-S,S-acetals and various arenes via direct substitution of the hydroxy group in alcohols has been developed. On the basis of this C-C coupling reaction, a series of bio- and pharmacologically important 3,4-disubstituted dihydrocoumarins, difficult to obtain by other methods, were prepared in high yields by a sequential Friedel-Crafts alkylation and intramolecular annulation reaction of alpha-hydroxyketene acyclic-S,S-acetals with phenols under mild conditions.
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