Cyclic amines are high-value molecules found in both natural products (alkaloids, proline…) and small-molecule therapeutics. The development of strategies for the selective and divergent functionalization of these derivatives can provide new opportunities for the discovery and evolution of materials of high relevance to our society. In general, cyclic amines are functionalised by introduction of new functionalities in place of C–H bonds. In this work we propose a fundamentally novel way to modify amines by means of radical deconstruction and tandem functionalization. This strategy will convert these cyclic materials into acyclic ones and further introduce additional substituents. The chemistry will involve amine activation by simple coordination with BH3. This will enable access to a boryl radical that can undergo e fast fragmentation followed by a radical functionalization process. Overall, this strategy will constitute a divergent platform for the diversification of high-value amines and also a novel retrosynthetic tactic for the preparation of acyclic derivatives. This research squarely fits within the expertise of the Leonori group in the generation and use of boryl radicals in synthesis and catalysis. The completion of such an innovative and ambitious project at RWTH Aachen University will be facilitated by generating, transferring, sharing and disseminating knowledge, and will enhance the Researcher future career following the training plan envisioned.