Direct alkenylation of alkylazaarenes with aldehydes through C(sp3)–H functionalization under catalytic InCl3 activation

Abstract

Under the influence of InCl3 as a Lewis acid catalyst, a methodology on the C(sp3)–H functionalization of alkylazaarenes has been demonstrated through the activation of benzylic C–H bonds towards their addition reaction with the appropriate electrophiles. This methodology was chiefly applied in the direct alkenylation of primary and secondary benzylic C–H bonds of alkylazaarenes with aldehydes. A variety of alkenyl products were afforded in generally good yields including the starting alkenyl intermediate used in the synthesis of montelukast and other related molecules.