Resolving a Reactive Organometallic Intermediate from Dynamic Directing Group Systems by Selective C−H Activation

Catalyst discovery from systems of potential precursors is a challenging endeavor. Herein, a new strategy applying dynamic chemistry to the identification of catalyst precursors from C−H activation of imines is proposed and evaluated. Using hydroacylation of imines as a model reaction, the selection of an organometallic reactive intermediate from a dynamic imine system, involving many potential directing group/metal entities, is demonstrated. The identity of the amplified reaction intermediate with the best directing group could be resolved in situ by ESI‐MS, and coupling of the procedure to an iterative deconvolution protocol generated a system with high screening efficiency.