Water-Tolerant IminiumReactive Species for Tyrosine-SpecificFunctionalization

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We report a novel, metal-free, andbiocompatible methodfor tyrosine-specificfunctionalization using kinetically persistent iminium intermediatesin aqueous media. By employing weakly coordinating anion-based ion-paircatalysts, this approach overcomes the inherent instability of iminiumspecies in water, enabling efficient conjugation with phenolic compounds.The method showcases broad applicability, including the functionalizationof pharmaceuticals, phenol-containing natural products, and tyrosineresidues in biopolymers, all under mild and environmentally friendlyconditions. Importantly, the approach preserves stereochemical integrityduring biomolecule modifications and achieves high chemo- and regioselectivity.This work offers a versatile platform for biofunctionalization, withpotential applications in drug discovery, therapeutic innovation,and biomolecular engineering.