Differentially protected, benzenediboronic acids: Divalent cross-coupling modules for the efficient synthesis of boron-substituted oligoarenes

On the basis of the boron-masking strategy, new divalent cross-coupling modules have been designed for the efficient synthesis of boron-substituted oligoarenes. The modules, i.e., monoprotected o-, m-, and p-benzenediboronic acid derivatives, undergo highly selective Suzuki-Miyaura coupling with Sp(2) iodides, bromides, chlorides, and triflates, affording coupling products in which the protected boronyl groups are left intact.