Sequential ortho-C-H and ipso-C-O Functionalization Using a Bifunctional Directing Group.

Design of C-H activation directing groups that can serve as electrophiles for subsequent cross-coupling significantly improves the step economy of synthetic applications of directed C-H functionalization. Through using a well-defined bifunctional template, palladium-catalyzed ortho-C-H alkenylation and arylation of benzylic alcohols was achieved via an end-on nitrile-embedded 12-membered macrocyclic transition state. Thereafter, the directing template is used as a handle for palladium-catalyzed ipso-C-O cross-coupling to provide functionalized diarylmethanes.