Functional group transformation represents a potent strategy for enriching the chemical diversity in DNA-encoded chemical library (DEL) synthesis. Within the realm of functional group transformation reactions, oxidation stands out as a predominant and facile approach to deliver altered chemical reactivity. However, reports on DNA-compatible oxidative reactions facilitating functional group transformations remain limited. Herein, we present a DNA-compatible K2RuO4-mediated oxidation methodology, which enables the in situ generation of carboxylic acids from alcohols and nitriles from primary amines, respectively. With several advantages, such as mild reaction conditions, high conversion rates, and broad substrate scopes, this oxidative transformation facilitates the potential utilization of carboxylic and nitrile groups as reactive handles in DEL synthesis. This work implicates how oxidation could be harnessed as a versatile approach to expand the chemical space of DEL for potential drug discovery purposes.

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