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Directing groups facilitate the activation of inert C\u2212O bonds in under\u2010utilized aryl methyl ethers enabling their adaptation for C\u2212C cross\u2010coupling reactions as less toxic surrogates to the ubiquitous haloarenes. The method reported enables C\u2212C cross\u2010coupling with readily available and economical arylboronic acid reagents, which is unprecedented, and compares well with other organoboron reagents with similarly high reactivity. Extension to directing group assisted chemo\u2010selective C\u2212O bond cleavage, and further application towards the synthesis of novel bifunctionalized biaryls is reported. 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