研究领域
C–H Functionalization
The development of highly selective and practical organic transformations based on the C–H functionalization is currently an area of great research and interest, since the method can yield desired target compounds in fewer steps and with less wastes compared to the conventional pre-functionalization approaches. Professor Chang and his research group have been involved in the development of highly desirable C–H Activation methodologies, mainly since 2008. Based on the rich experiences, Chang's group will continue to develop the truly efficient and site-selective C–H activation strategies especially for C–C, C–N and C–O bond formations.
Methane (CH₄) Functionalization
Methane is abundant on Earth as a main constituent of natural gas and gas hydrate. Considering its utility, the conversion of methane into a useful chemical feedstock will be of great future use. However, there are intrinsic difficulties that hinder this transformation - extremely high C–H bond activation energy, high pka values, small polarizability. To overcome these difficulties, Chang's group will focus on the development of efficient and selective catalytic systems for controlling C–H activation of methane. Experimental and computational studies on methane activation and subsequent selective introduction of functional groups into methane will be conducted cooperatively.
Catalytic Selective Defunctionalization
An abundance of inexpensive bio-substrates can be derived from nature such as agricultural wastes, forest products, crop residues, or aquatic biomass, all of which are sustainable sources of organic carbons. While the structural portion of the bio-compounds are mainly composed of cellulose, hemicellulose, and lignin, the hydrolysis of these materials affords glucose and subsequent reduction gives bio-derived platform chemicals such as sugar alcohols. Therefore, selective defunctionalization of those substrates provides bio-based compounds such as hydrocarbons, methanol, higher molecular weight alkanes, alkenes, and methane. Although hydrogenolysis is utilized to cleave the C–C and C–O bond of bio-derived polyols (sugars and sugar alcohols), the present methods use heterogeneous catalysts under harsh conditions requiring high temperature and pressure and even non-selective. Therefore, Chang's group will concentrate on the development of selective catalytic systems allowing controlled defucntionalization of bio-derived flatform substrates under mild conditions, which will open a new avenue for the utilization of biomass-derived platform chemicals.
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Intramolecular Hydroamidation of Alkenes Enabling Asymmetric Synthesis of β-Lactams via Unprecedented Mechanism of NiH Catalysis Xiang Lyu, Changhyeon Seo, Hoimin Jung, Teresa Faber, Dongwook Kim, Sangwon Seo, and Sukbok Chang Nat. Catal. 2023, accepted
Mechanistic Snapshots of Rhodium-Catalyzed Acylnitrene Transfer Reactions Hoimin Jung, Jeonguk Kweon, Jong-Min Suh, Mi Hee Lim, Dongwook Kim, and Sukbok Chang Science 2023, 381, 525-532 (Free access [Link])
Regio- and Enantioselective Catalytic δ-C–H Amidation of Dioxazolones Enabled by Open-Shell Copper-Nitrenoid Transfer Suhyeon Kim, Se Lin Song, Jianbo Zhang, Dongwook Kim, Sungwoo Hong, and Sukbok Chang J. Am. Chem. Soc. 2023, 145, 16238-16248
Energy-transfer-induced [3+2] cycloadditions of N–N pyridinium ylides Wooseok Lee, Yejin Koo, Hoimin Jung, Sukbok Chang, and Sungwoo Hong Nat. Chem. 2023, DOI-10.1038/s41557-023-01258-2
Deconstructive Pyridylation of Unstrained Cyclic Amines through a One-Pot Umpolung Approach Seonghyeok Hong, Byeongseok Kweon, Wooseok Lee, Sukbok Chang, and Sungwoo Hong Org. Lett. 2023, 25, 2722-2727
Versatile Utility of Cp*Co(III) Catalysts in C–H Amination under Inner- and Outer-sphere Pathway Jeonghyo Lee and Sukbok Chang Synlett. 2023, 34, 1356–1366
Alcohol-Incorporating Diels–Alder Dimerization of In Situ Formed ortho-Quinamine via Co-Nitrenoid Insertion Jeonghyo Lee, Bora Kang, Dongwook Kim, and Sukbok Chang Org. Lett. 2022, 24, 5845–5850
Multidimensional Screening Accelerates the Discovery of Rhodium Catalyst Systems for Selective Intra- and Intermolecular C–H Amidations Jiwoo Jeong,† Hoimin Jung,† Dongwook Kim, and Sukbok Chang († equally contributed) ACS Catal. 2022, 12, 8127-8138
Endo-Selective Intramolecular Alkyne Hydroamidation Enabled by NiH Catalysis Incorporating Alkenylnickel Isomerization Hoonchul Choi,† Xiang Lyu,† Dongwook Kim, Sangwon Seo, and Sukbok Chang († equally contributed) J. Am. Chem. Soc. 2022, 144, 10064-10074
Photoinduced Transition Metal-Free Chan-Evans-Lam-Type Coupling: Dual Photoexcitation Mode with Halide Anion Effect Zijun Zhou,† Jeonguk Kweon,† Hoimin Jung, Dongwook Kim, Sangwon Seo, and Sukbok Chang († equally contributed) J. Am. Chem. Soc. 2022, 144, 9161-9171
Photoinduced α-C–H Amination of Cyclic Amine Scaffolds Enabled by Polar-Radical Relay Wongyu Lee, Dongwook Kim, Sangwon Seo, and Sukbok Chang Angew. Chem. Int. Ed. 2022, 61, e202202971
KOtBu-Catalyzed 1,2-Silaboration of N-Heteroarenes to Access 2-Silylheterocycles: A Cooperative Model for the Regioselectivity Eunchan Jeong,† Joon Heo,† Seongho Jin, Dongwook Kim, and Sukbok Chang († equally contributed) ACS Catal. 2022, 12, 4898-4905
Head-to-Head Homocoupling of Ynamides via a Dual Activation Mode of Triple Bonds by Half Sandwich Metal Complexes Manoj Kumar Sahoo,† Sourav Pradhan,† Dongwook Kim, Jung-Woo Park, and Sukbok Chang († equally contributed) Organometallics 2022, 41, 900-905
Chain Walking as a Strategy for Iridium-Catalyzed Migratory Amidation of Alkenyl Alcohols to Access α-Amino Ketones Yeongyu Hwang, Seung Beom Baek, Dongwook Kim, and Sukbok Chang J. Am. Chem. Soc. 2022, 144, 4277-4285
On the Origin of Rh-Catalyzed Selective Ring-Opening Amidation of Substituted Cyclopropanols to Access β²-Amino Ketones Minhan Lee, Joon Heo, Dongwook Kim, and Sukbok Chang J. Am. Chem. Soc. 2022, 144, 3667-3675
C2-Selective, Functional Group Divergent Amination of Pyrimidines by Enthalpy-Controlled Nucleophilic Functionalization Won Seok Ham, Hoonchul Choi, Jianbo Zhang, Dongwook Kim, and Sukbok Chang J. Am. Chem. Soc. 2022, 144, 2885-2892
Iridium-Catalyzed Amidation of In Situ Prepared Silyl Ketene Acetals to Access α-Amino Esters Yunyeong Gwon,† Minhan Lee,† Dongwook Kim, and Sukbok Chang († equally contributed) Org. Lett. 2022, 24, 1088-1093
Access to β-Lactams via Iron-Catalyzed Olefin Oxyamidation Enabled by π-Accepting Phthalocyanine Ligand Jeonguk Kweon, Dongwook Kim, Seungju Kang, and Sukbok Chang J. Am. Chem. Soc. 2022, 144, 1872-1880
Ir(III)-Catalysed electrooxidative intramolecular dehydrogenative C−H/N−H coupling for the synthesis of N−H indoles Youyoung Kim, Dongwook Kim, and Sukbok Chang Chem. Commun. 2021, 57, 12309-12312
Cobalt-Nitrenoid Insertion-Mediated Amidative Carbon Rearrangement via Alkyl-Walking on Arenes Jeonghyo Lee, Bora Kang, Dongwook Kim, Jia Lee, and Sukbok Chang J. Am. Chem. Soc. 2021, 143, 18406-18412
Visible-Light Induced C(sp²)–H Amidation with an Aryl–Alkyl σ-Bond Relocation via Redox-Neutral Radical-Polar Crossover Hyeyun Keum,† Hoimin Jung,† Jiwoo Jeong, Dongwook Kim, Sukbok Chang († equally contributed) Angew. Chem. Int. Ed. 2021, 60, 25235-25240
Regioselective Access to α-Vinylsilanes and α-Vinylgermanes by Cobalt-catalyzed Migratory Hydrofunctionalization of 2-Alkynes Manoj Kumar Sahoo, Dongwook Kim, Sukbok Chang, and Jung-Woo Park ACS Catal. 2021, 11, 12777-12784
Seongho Jin, Jinwoo Kim, Dongwook Kim, Jung-Woo Park, and Sukbok Chang "Electrolytic C–H Oxygenation via Oxidatively Induced Reductive Elimination in Rh Catalysis" ACS Catal., 2021, 11, 6590-6595
Seung Youn Hong, Yeongyu Hwang, Minhan Lee, and Sukbok Chang "Mechanism-Guided Development of Transition-Metal Catalyzed C–N Bond-Forming Reactions Using Dioxazolones as the Versatile Amidating Source" Acc. Chem. Res., 2021, In Press
Torben Rogge, Nikolaos Kaplaneris, Naoto Chatani, Jinwoo Kim, Sukbok Chang, Benudhar Punji, Laurel L Schafer, Djamaladdin (Jamal) Musaev, Joanna Wencel-Delord, Charis Roberts, Richmond Sarpong, Zoe Wilson, Margaret Brimble, Magnus Johansson, and Lutz Ackermann "C-H Activation"Nature Reviews Methods Primers, 2021, Accepted
Hao Wang, Hoimin Jung, Fangfang Song, Shiyang Zhu, Ziqian Bai, Danye Chen, Gang He, Sukbok Chang, and Gong Chen "Nitrene-mediated intermolecular N–N coupling for efficient synthesis of hydrazides" Nat. Chem., 2021, 13, 378–385
Hyun Ji Jeon, Wongyu Lee, Sangwon Seo, and Sukbok Chang "N-Chloro-N-sodio-carbamates as a Practical Amidating Reagent for Scalable and Sustainable Amidation of Aldehydes under Visible Light" Org. Process Res. Dev.,2021, 25, 1176-1183.
Euijae Lee†, Yeongyu Hwang†, Yeong Bum Kim, Dongwook Kim, and Sukbok Chang (†: equally contributed) "Enantioselective Access to Spirolactams via Nitrenoid Transfer Enabled by Enhanced Noncovalent Interactions" J. Am. Chem. Soc., 2021, 143, 6363-6369
Xiang Lyu, Jianbo Zhang, Dongwook Kim, Sangwon Seo, and Sukbok Chang "Merging NiH Catalysis and Inner-Sphere Metal-Nitrenoid Transfer for Hydroamidation of Alkynes" J. Am. Chem. Soc., 2021, 143, 5867-5877
Jeonghyo Lee, Seongho Jin, Dongwook Kim, Soon Hyeok Hong, Sukbok Chang "Cobalt-Catalyzed Intermolecular C–H Amidation of Unactivated Alkanes" J. Am. Chem. Soc., 2021, 143, 5191−5200
Suhyeon Kim, Dongwook Kim, Seung Youn Hong, and Sukbok Chang "Tuning Orbital Symmetry of Iridium Nitrenoid Enables Catalytic Diastereo- and Enantioselective Alkene Difunctionalizations" J. Am. Chem. Soc., 2021, 143, 3993-4004.
Yeong Bum Kim, Joonghee Won, Jeonghyo Lee, Junho Kim, Bingwei Zhou, Jung-Woo Park, Mu-Hyun Baik, and Sukbok Chang "Ni-Catalyzed Intermolecular C(sp3)–H Amidation Tuned by Bidentate Directing Groups" ACS Catal., 2021, 11, 3067-3072.
Wongyu Lee†, Hyun Ji Jeon†, Hoimin Jung, Dongwook Kim, Sangwon Seo, and Sukbok Chang (†: equally contributed) "Controlled Relay Process to Access N-Centered Radicals for Catalyst-Free Amidation of Aldehydes under Visible Light" Chem, 2021, 7, 495-508.
Jinwoo Kim, Seongho Jin, Dongwook Kim, and Sukbok Chang "Oxidatively Induced Reductive Elimination for Methyl Group Transfer via Isolable Transmetalation Complexes"Bull. Kor. Chem. Soc. 2021, 42, 529-532.
Yeong Bum Kim, Dongwook Kim, Shashikant U. Dighe, Sukbok Chang, and Jung-Woo Park "Cobalt-Hydride-Catalyzed Hydrosilylation of 3-Alkynes Accompanying π-Bond Migration" ACS Catal., 2021, 11, 1548-1553.
Seung Youn Hong, Dongwook Kim, and Sukbok Chang "Catalytic Access to Carbocation Intermediates via Nitrenoid Transfer Leading to Allylic Lactams" Nat. Catal., 2021, 4, 79-88.
Jeonguk Kweon and Sukbok Chang "Highly Robust Iron Catalyst System for Intramolecular C(sp3)-H Amidation Leading to γ-Lactams"Angew. Chem. Int. Ed., 2021, 60, 2909-2914.
Weilong Xie, Dongwook Kim, and Sukbok Chang "Copper-Catalyzed Formal Dehydrogenative Coupling of Carbonyls with Polyfluoroarenes Leading to β-C–H Arylation" J. Am. Chem. Soc., 2020, 142(49), 20588-20593
Jinwoo Kim, Dongwook Kim, and Sukbok Chang "Merging Two Functions in a Single Rh Catalyst System: Bimodular Conjugate for Light-Induced Oxidative Coupling" J. Am. Chem. Soc., 2020, 142(45), 19052-19057.
Youyoung Kim, Joon Heo, Dongwook Kim, Sukbok Chang and Sangwon Seo "Ring-Opening Functionalizations of Unstrained Cyclic Amines Enabled by Difluorocarbene Transfer" Nat. Commun., 2020, 11, 4761.
Jianbo Zhang and Sukbok Chang "cine-Silylative Ring-Opening of α-Methyl Azacycles Enabled by the Silylium-Induced C-N Bond Cleavage" J. Am. Chem. Soc., 2020, 142(29), 12585-12590.
Minhan Lee, Hoimin Jung, Dongwook Kim, Jung-Woo Park, and Sukbok Chang "Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters" J. Am. Chem. Soc., 2020, 142(28), 11999-12004
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