Pohang University of Science and Technology · Chemistry
Professor Hyunwoo Kim's research lab specializes in the development of innovative electrochemical and radical-based methodologies for the selective and sustainable synthesis of medicinally relevant molecules. The lab focuses on the strategic incorporation of fluorinated functional groups—particularly the difluoromethyl (CF₂H) group—into complex organic frameworks to enhance drug-like properties such as metabolic stability and permeability. Central to their work is the use of electrochemistry to enable mild, selective, and sustainable transformations, including difluoromethylation, C–H amination, and heterocycle formation, often avoiding traditional stoichiometric oxidants or specialized reagents. The lab also emphasizes mechanistic understanding through electrochemical and computational studies to guide the design of new catalytic systems.
Figures are computed from collected data and may differ slightly.
Due to its superior ability in controlling pharmaceutical activity, the installation of difluoromethyl (CF<sub>2</sub>H) functionality into organic molecules has been an area of intensive research. In this context, difluoromethylation of C-C π bonds mediated by a CF<sub>2</sub>H radical have been pursued as a central strategy to grant access to difluoromethylated hydrocarbons. However, early precedents necessitate the generation of oxidative chemical species that can limit the generality and uti
The difluoromethyl group (CF<sub>2</sub>H) serves as an essential bioisostere in drug discovery campaigns according to Lipinski's Rule of 5 due to its advantageous combination of lipophilicity and hydrogen bonding ability, thereby improving the ADME properties. However, despite the high prevalence and importance of vicinal hydrogen bond donors in pharmaceutical agents, a general synthetic method for doubly difluoromethylated compounds in the vicinal position is absent. Here we describe a copper-
The difluoromethyl (−CF2H) group has gained considerable significance in synthetic and medicinal chemistry due to its ability to modulate molecular properties, including electronic effects and hydrogen-bonding capability. Traditional difluoromethylation methods often require specialized reagents and demanding reaction conditions, potentially limiting their applicability across diverse substrates. Electrochemical difluoromethylation has emerged as an alternative approach that enables the in situ
We described a silver(I)-mediated intramolecular oxidative C-H amination that enables the construction of assorted 1<i>H</i>-indazoles that are widely applicable in medicinal chemistry. The developed amination was found to be efficient for the synthesis of a variety of 3-substituted indazoles that are otherwise difficult to be synthesized by other means of C-H aminations. Preliminary mechanistic studies suggested that the current amination proceeds via single electron transfer (SET) mediated by
Abstract We describe a catalyst, oxidant, and coupling‐reagent free strategy to access 4‐membered heterocycles, representing a unique example of visible‐light triggered intramolecular cyclization of propargylic alcohols and amines to access oxetanones and azetidinones respectively. Despite the direct 4‐endo‐dig cyclization from these starting materials has proven to be unfavorable, the formation of key p ‐quinone methide intermediacy allows an efficient bypass for regioselective 4‐exo‐trig cycli
We present highly efficient and operationally simple synthetic methods for 1,2-aminoalcohols via electroreductive cross aza-pinacol coupling between <i>N</i>-acyl diarylketimines and aldehydes. Preliminary mechanistic studies including cyclic voltammetry and density functional theory (DFT) calculations suggest that the reaction is instigated by selective electrochemical single electron transfer (SET) of <i>N</i>-acylketimines. The developed electrochemical protocol is compatible to biorelevant f
We present a catalyst-free strategy that combines photochemical and electrochemical activation to unlock unique reactivity in otherwise less reactive molecules. Photochemical excitation generates intermediates that can undergo electrochemical oxidation to form highly electrophilic species that can engage weak nucleophiles, enabling the synthesis of diverse heterocycles under mild conditions. Mechanistic studies, including voltammetric, spectroscopic, and computational analyses, suggest that a li
The selection of electrode material is a critical factor that determines the selectivity of electrochemical organic reactions. However, the fundamental principles governing this relationship are still largely unexplored. Herein, we demonstrate a photoelectrocatalytic (PEC) system as a promising reaction platform for the selective radical-radical coupling reaction owing to the inherent charge-transfer properties of photoelectrocatalysis. As a model reaction, the radical trifluoromethylation of ar
Due to the unique reactivity of open-shell intermediates, the development of catalytic transformations driven by single-electron transfer (SET) has been an area of intense research in organic chemistry. In particular, the employment of unconventional means of activation, including photoredox catalysis and electrocatalysis, has provided unique entry to single-electron reactivities and led to new solutions to challenging synthetic problems that are not readily addressed using existing tools. We di
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