Towards the understanding of palladium-catalyzed tandem cyclopropanol opening-direct arylation reactions

Insight into the stereoelectronic requirements for intramolecular direct arylation reactions is presented. Substrates were designed and synthesized with the goal of elucidating the steric, electronic, and conformational requirements for the concerted metalation-deprotonation process in intramolecular direct arylation reactions.

Poor conversions and yields were obtained with rotationally-constrained systems not possessing electron-withdrawing, or activating, groups on the aryl ring. Systems containing both activated and unactivated protons participating in CMD showed full selectivity for the activated protons.