Hyun Jin Kim

Korea Research Institute of Chemical Technology

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Sukbok Chang

Korea Advanced Institute of Science and Technology

Min Kim

Chungbuk National University

Jinho Kim

Incheon National University

Manjaly J. Ajitha

King Abdullah University of Science and Technology

Kwangho Yoo

Ruhr University Bochum

Seung Hwan Cho

Pohang University of Science and Technology

Ung Chan Yoon

Pusan National University

Yousung Jung

Seoul National University

Patrick S. Mariano

University of New Mexico

Jong Yeon Hwang

Korea Research Institute of Chemical Technology

Cooperative Institutions

Korea Research Institute of Chemical Technology

Government of the Republic of Korea

Sungkyunkwan University

Korea Advanced Institute of Science and Technology

Korea University of Science and Technology

Seoul National University

Chungbuk National University

Daejeon University

Chungnam National University

Pusan National University

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Copper-Mediated Three-Component Reaction for the Synthesis of N-Acylsulfonamide on DNA

Organic Letters (2022)

Solji Eom Taeyeon Kwon Da Yeon Lee Chi Hoon Park Hyun Jin Kim

The DNA-encoded library (DEL) technology is a new method for discovering hit compounds for target proteins in the pharmaceutical industry. The N-acylsulfonamide functional group has been reported to exhibit various pharmacological activities, and based on this, the demand for a method that allows its introduction into the DEL platform has increased. In this report, a procedure for synthesizing N-acylsulfonamide functional groups applicable to DEL construction was developed in the presence of a copper reagent and water as a nucleophile from simple alkynes or sulfonyl azides, which are widely commercially available. Furthermore, we prove that a new alternative procedure can be used to construct a DNA-encoded library.

Sulfonyl

Functional group

Component (thermodynamics)

10.1021/acs.orglett.2c01675

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Citations (9)

Discovery of pan-IAP degraders via a CRBN recruiting mechanism

European Journal of Medicinal Chemistry (2022)

Seulki Park Dayoung Kim Woori Lee Jin Hwa Cho Sung Young Kim

XIAP

Cereblon

Inhibitor of apoptosis

Proteolysis

10.1016/j.ejmech.2022.114910

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Citations (5)

Hydrogen-Bond-Assisted Controlled C–H Functionalization via Adaptive Recognition of a Purine Directing Group

Journal of the American Chemical Society (2013)

Hyun Jin Kim Manjaly J. Ajitha Yongjae Lee Jaeyune Ryu Jin Kim

We have developed the Rh-catalyzed selective C-H functionalization of 6-arylpurines, in which the purine moiety directs the C-H bond activation of the aryl pendant. While the first C-H amination proceeds via the N1-chelation assistance, the subsequent second C-H bond activation takes advantage of an intramolecular hydrogen-bonding interaction between the initially formed amino group and one nitrogen atom, either N1 or N7, of the purinyl part. Isolation of a rhodacycle intermediate and the substrate variation studies suggest that N1 is the main active site for the C-H functionalization of both the first and second amination in 6-arylpurines, while N7 plays an essential role in controlling the degree of functionalization serving as an intramolecular hydrogen-bonding site in the second amination process. This pseudo-Curtin-Hammett situation was supported by density functional calculations, which suggest that the intramolecular hydrogen-bonding capability helps second amination by reducing the steric repulsion between the first installed ArNH and the directing group.

Surface Modification

Moiety

Functional group

10.1021/ja4118472

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Citations (147)

Intramolecular Oxidative Diamination and Aminohydroxylation of Olefins under Metal-Free Conditions

Organic Letters (2012)

Hyun Jin Kim Seung Hwan Cho Sukbok Chang

A metal-free procedure that is simple to operate and convenient to handle was developed for the facile intramolecular oxidative diamination of olefins using an iodobenzene diacetate oxidant and a halide additive to furnish bisindolines at room temperature. The present reaction is featured by mild conditions, a broad substrate scope, and excellent functional group tolerance. The same protocol was successfully extended to the aminohydroxylation.

Iodobenzene

Functional group

10.1021/ol300166q

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Citations (92)

Synthese aromatischer Nitrile mithilfe nichtmetallischer CN‐Quellen

Angewandte Chemie (2012)

Jinho Kim Hyun Jin Kim Sukbok Chang

Abstract Aromatische Nitrile werden effizient durch die übergangsmetallkatalysierte Cyanierung von Aryl(pseudo)halogeniden mit metallischen CN‐Quellen wie CuCN, KCN, NaCN, Zn(CN) 2 , TMSCN oder K 4 [Fe(CN) 6 ] synthetisiert. Nachteilig an diesen Verfahren sind jedoch die stöchiometrischen Mengen von Metallabfall, die Vergiftung des Metallkatalysators oder die Bildung von toxischem HCN‐Gas. Für die Cyanierung von Aryl‐Halogen‐ und Aryl‐H‐Bindungen wird daher seit einiger Zeit auch eine Reihe von “nichtmetallischen” organischen CN‐Quellen erkundet. Dieser Kurzaufsatz stellt verschiedene nichtmetallische CN‐Quellen und ihre Anwendung für die Synthese von Arylnitrilen vor.

10.1002/ange.201206168

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Citations (64)

Transformation of tert‐Butyl Amide Directing Groups to Nitriles in Iridium‐Catalyzed C−H Bond Functionalizations

Asian Journal of Organic Chemistry (2021)

Dopil Kim Haneul Yoo Myung Hwan Park Youngjo Kim Gary Jing Chuang

Abstract To overcome limitations of the directing group in IrCp* catalysis for C−H functionalization, we developed a directing group transformation strategy that was applied after obtaining the desired products. Well‐established Ir‐catalyzed alkenylation, alkylation, and arylation reactions were performed under mild conditions, and then the stable coordinating amide groups were efficiently converted to versatile nitrile groups by in situ treatment with Vilsmeier reagent at room temperature. Whereas the conversion of primary amides has been extensively studied with modified Appel protocol, nitrile formation from secondary amides is very limited. Various ortho ‐functionalized benzonitrile derivatives (31 examples) were synthesized using this simple methodology, and the subsequent oxidative cyclization of an ortho ‐alkenylated product was investigated to demonstrate the synthetic utility of this strategy. This simple and versatile methodology should be available under various transition metal catalysis with stable amide directing groups.

Amide

Benzonitrile

Functional group

10.1002/ajoc.202100641

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Citations (3)

ChemInform Abstract: Intermolecular Oxidative C—N Bond Formation under Metal‐Free Conditions: Control of Chemoselectivity Between Aryl sp² and Benzylic sp³ C—H Bond Imidation.

ChemInform (2012)

Hyun Jin Kim Jiyu Kim Seung Hwan Cho Sukbok Chang

Abstract Arenes undergo efficient imidation in the presence of Ph‐I(OAc) 2 .

Chemoselectivity

10.1002/chin.201214037

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Citations (0)

ChemInform Abstract: Hydrogen‐Bond‐Assisted Controlled C—H Functionalization via Adaptive Recognition of a Purine Directing Group.

ChemInform (2014)

Hyun Jin Kim Manjaly J. Ajitha Yongjae Lee Jaeyune Ryu Jin Kim

10.1002/chin.201432044

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Citations (0)

Ir-Catalyzed C–H Amidation Using Carbamoyl Azides for the Syntheses of Unsymmetrical Ureas

The Journal of Organic Chemistry (2020)

Kwangho Yoo Jooyeon Lee Myung Hwan Park Youngjo Kim Hyun Jin Kim

An iridium-catalyzed C–H amidation for the syntheses of unsymmetrical urea was developed using carbamoyl azides (R(R′)N–C(O)-N3) as the nitrogen source. A combination of iridium and silver gave an active catalyst for C–N bond formation. A variety of urea derivatives were synthesized using carbamoyl azides with only dinitrogen byproducts. Finally, the use of the transient directing group strategy with carbamoyl azides extended the substrate scope of the catalytic C–H amidation to yield aldehyde-containing unsymmetrical ureas.

10.1021/acs.joc.0c00659

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Citations (11)

Photoredox-catalyzed halotrifluoromethylations of alkynes with triethylammonium halides: synthesis of tetrasubstituted alkenes containing CF₃ and halogens

Organic Chemistry Frontiers (2020)

Woori Lee Yeonhee Lee Minjin Yoo Soo Bong Han Hyun Jin Kim

The introduction of F- and CF₃-groups into alkynes is enabled by photocatalysis under mild conditions. The developed method can be extended to providing chloro- and bromotrifluoromethylated alkynes and bioactive compounds functionalization.

Surface Modification

10.1039/d0qo00893a

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Citations (20)