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(Pinacolato)boryl  ortho ‐silyl(hetero)aryl triflates are presented as a new class of building blocks for arylation. They demonstrate unique versatility by delivering boronate or (hetero)aryne reactivity chemoselectively in a broad range of transformations. This approach enables the unprecedented postfunctionalization of fluoride‐activated (hetero)aryne precursors, for example, as substrates in transition‐metal catalysis, and offers valuable new possibilities for aryl boronate postfunctionalization without the use of specialized protecting groups.

Boryl (Hetero)aryne Precursors as Versatile Arylation Reagents: Synthesis through CH Activation and Orthogonal Reactivity