Palladium(II) Catalyzed C–H Functionalization Cascades for the Diastereoselective Synthesis of Polyheterocycles

C–H activation offers huge potential in the generation of complex structures from simple starting materials. Herein we report the development of a highly diastereoselective palladium(II) catalyzed C–H functionalization cascade to produce novel, unsaturated polyheterocycles from simple diene-tethered heterocyclic starting materials. The reaction is applicable to both indole and pyrrole based substrates and tolerates a wide range of functional group substitutions around the heteroaromatic core. The polyheterocyclic products are formed as single diastereoisomers, with two new stereocenters formed in a single step.