Allylation and cyanation of aza-aromatics activated by chloroformate and a catalytic amount of iodine

Allyltrimethylsilane and trimethylsilyl cyanide undergo smooth addition to N-acylated quinolines in the presence of a catalytic amount of iodine to afford 2-allyl- and 2-cyano-1,2-dihydroquinoline derivatives, respectively in good yields with high chemo- and regioselectivity. A variety of functional groups such as alkyl, alkoxy, halo, and nitro functionalities are tolerated under the reaction conditions. © 2005 Elsevier Ltd. All rights reserved.