AlCl3-mediated direct carbon-carbon bond-forming reaction of alpha-hydroxyketene-S,S-acetals with arenes and synthesis of 3,4-disubstituted dihydrocoumarin derivatives.
A simple and efficient AlCl(3)-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.
Piao
Cheng-Ri
CR
Department of Chemistry, Northeast Normal University, Changchun, 130024, People's Republic of China.
Zhao
Yu-Long
YL
Han
Xiao-Dan
XD
Liu
Qun
Q