An efficient method for the C(2)−H arylation of (benz)imidazoles and (benz)oxazoles with aryl chlorides and aryl bromides under Ni/NHC catalysis has been developed. The main benefit of the method is the in situ generation of active Ni/NHC complexes from the air‐tolerant bench‐stable precursors NiCl2Py2, IMes⋅HCl, and potassium tert‐butoxide, which plays a dual role as base and Ni(II) to Ni(0) reductant. The approach represents a user‐friendly alternative for procedures relying on the use of toxic phosphine ligands or unstable air‐sensitive Ni(cod)2. The concept highlighted in the present study shows that mapping a competitive picture of catalyst dynamics and revealing the competitive processes towards the destruction and stabilization of catalytically active species enables a highly efficient catalytic system to be built under simple conditions.

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