Chemistry Letters, Vol.33, No.5, 590-591, 2004
KCN-catalyzed C-C bond formation between imine and gem-difluoroalkene moieties: A facile synthesis of 2,4-disubstituted 3-fluoroquinolines
Intramolecular cyclization of beta,beta-difluoro-o-methyleneaminostyrenes leading to 3-fluoroquinolines is efficiently promoted by a catalytic amount of KCN and a small excess of K2CO3. The reaction proceeds via (i) the generation of intramolecular carbon nucleophiles from imine moieties and (ii) the cyclization by their substitution for the vinylic fluorine.