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Selective Mechanochemical Monoarylation of Unbiased Dibromoarenes by In-situ Crystallization.

Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of liquid, unbiased dibromoarenes under mechanochemical conditions selectively afford the monoarylated products. The lower reactivity of the crystalline monoarylated products rela-tive to the liquid starting materials should be attributed predom-inantly to the low diffusion efficiency of the former in the re-action mixture, which results in a selective monoarylation. The present study sheds light on a novel approach using in-situ phase transitions in solids to design selective organic transfor-mations that are difficult to achieve via conventional solution-based synthesis.