Our research program is focused on developing selective and sustainable chemical transformations to enable streamlined synthesis of functionalized molecules from accessible feedstocks. Synthetic transformations involving radical or radical ion intermediates under photocatalytic or electrochemical conditions are of particular interests, due to the versatile reactivities exhibited by those open-shell radical intermediates under mild conditions. Our research program is divided into two general areas: (1) developing electrosynthetic and electrocatalytic methods for the sustainable functionalization of abundant chemical feedstocks, such as alcohols and amines, and (2) the discovery and optimization of electron donor-acceptor (EDA) photocatalysts for selective functionalization of strong aromatic and aliphatic C–H bonds.

• Surface functionalized and nanostructured electrodes-enabled redox reactions

    Electrochemistry represents an ideal platform to perform radical reactions with outstanding controllability and sustainability. We aim to develop novel geometrically and chemically functionalized electrode constructions to unlock new electrochemical reactions. Applications include redox-neutral transformations that require cooperative oxidative and reductive half reactions and precise control of electron transfer selectivity by covalent or non-covalent modification of electrode surfaces, to kinetically favor oxidation/reduction of a particular substrate.

• Electrochemical Nucleophilic Functionalization of Alcohols.

        Mitigating reactivities and selectivity of radical transformations still lacks general solution in modern organic synthesis. To address this challenge, we aim to achieve selective C­−H activation of hydrocarbons by an intramolecular proton-coupled electron transfer (PCET) mechanism. Selectivity will be leveraged by the binding geometry of the substrate with the molecular catalyst, and the reactive site in proximity to the catalyst will be kinetically favored for chemical transformation.

• Photocatalytic C–H Activation via Electron Donor-Acceptor (EDA) Adducts

    Carbon-centered radicals are very important intermediates in organic synthesis of fine chemical products and pharmaceutical intermediates, due to their versatile reactivities to form various C–C, C–O, and C–N bonds among others. The most atomically economic way to generate carbon-centered radicals is by direct cleavage of C–H bonds via H-atom transfer (HAT). Among various known HAT reactions, the chemoselectivity is generally controlled by thermodynamics. Namely, the weakest C–H bond with the lowest bond dissociation free energy (BDFE) is the most susceptible to be cleaved. Herein, we aim to develop photocatalytic strategies to override this intrinsic selectivity and activate stronger aromatic and aliphatic C–H bonds in the presence of weaker ones.