A Guide to Directing Group Removal: 8-Aminoquinoline

The use of directing groups allows high levels of selectivity to be achieved in transition metal-catalyzed transformations. Efficient removal of these auxiliaries after successful functionalization, however, can be very challenging. This review provides a critical overview of strategies used for removal of Daugulis' 8-aminoquinoline (2005-2020), one of the most widely used N,N-bidentate directing groups. The limitations of these strategies are discussed and alternative approaches are suggested for challenging substrates. Our aim is to provide a comprehensive end-users' guide for chemists in academia and industry who want to harness the synthetic power of directing groups-and be able to remove them from their final products.

Automated summary

This review discusses strategies for efficient removal of directing groups, focusing on the widely used N,N-bidentate directing group 8-aminoquinoline. The limitations of these strategies and alternative approaches for challenging substrates are also discussed. The aim is to provide a comprehensive guide for chemists in academia and industry to harness the synthetic power of directing groups and remove them from final products.