Koh, Ming Joo - National University of Singapore - Department of Chemistry, Faculty of Science

个人简介

EDUCATION Ph.D. & Post-Doc in Organic Chemistry (2012–2018), Boston College, MA, USA Advisor: Prof. Amir H. Hoveyda B.Sc. in Chemistry & Biological Chemistry, First Class Honors (2008–2012), Nanyang Technological University, Singapore Advisor: Prof. Philip Wai Hong Chan Ming Joo (MJ) Koh was born and raised on the sunny island of Singapore. As a research assistant in Professor Philip Chan's group during his undergraduate years at Nanyang Technological University (NTU), MJ worked on a number of projects that employed gold-catalyzed alkene and alkyne cycloisomerization transformations to furnish architecturally distinct heterocyclic compounds. Upon graduating from NTU with a Bachelor of Science (First Class Honours) degree, MJ pursued his Ph.D. and post-doctoral studies under the tutelage of Professor Amir H. Hoveyda at Boston College, USA. In collaboration with Professor Richard R. Schrock's group at Massachusetts Institute of Technology, MJ's doctoral research mainly focused on developing catalytic stereoselective olefin metathesis protocols to access stereoisomerically pure alkenes for applications in natural product and pharmaceutical synthesis. As a post-doctoral fellow, MJ shifted his focus to developing catalytic stereoselective transformations involving organofluorine compounds. In June 2018, MJ was awarded the President's Assistant Professorship to commence his independent studies at the Chemistry Department of the National University of Singapore. ACADEMIC APPOINTMENTS Deputy Head of Research, Department of Chemistry, NUS: 2024-present Dean's Chair Professor, NUS: 2024-2027 Associate Professor (with Tenure), NUS: 2023-present President's Assistant Professor, NUS: 2018-2023 AWARDS & HONORS Mitsui Chemicals Catalysis Science Award for Creative Work: 2024 Novartis Early Career Award in Chemistry: 2023 Asian Core Program Lectureship Award (Taiwan): 2023 Nanyang Outstanding Young Alumni Award, NTU: 2023 Young Researcher Award, NUS: 2023 Asian Scientist 100: 2023 Faculty Young Scientist Award, Faculty of Science, NUS: 2022 Young Scientist Award, SNAS: 2022 Asian Core Program Lectureship Award (Japan, Korea): 2022 C&EN's Talented 12: 2022 Thieme Chemistry Journals Award: 2022 TCI-SNIC Industry Award in Synthetic Chemistry: 2021 Innovators Under 35 (TR35) Asia Pacific Award: 2021 Excellent Young Teacher Award: 2019-2020 Asian Core Program Lectureship Award (China, Thailand): 2019 NUS Inauguration Grant: 2019 BMS Graduate Fellowship in Synthetic Organic Chemistry: 2016-2017 LaMattina Family Graduate Fellowship in Chemical Synthesis: 2016

研究领域

(a) Discovery of reaction systems that engage radicals in cross-coupling transformations. (b) Development of synthetic protocols for the stereoselective synthesis of carbohydrates. (c) Photochemical, electrochemical and/or base metal-catalyzed synthesis of druglike molecules. (d) Development of catalytic regio- and stereoselective alkene functionalization reactions. (e) Design of new heterogeneous single-atom catalysts for liquid-phase organic synthesis (collaboration with materials chemists). (f) Elucidation of reaction mechanisms via mechanistic and computational studies (collaboration with computational chemists). (g) Plastic waste upcycling using base metal catalysis (collaboration with materials chemists).

近期论文

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Yang, T.*; Xiong, W.; Su, G.; Yang, W.; Lu, M.; Koh, M. J.* "Multicomponent Construction of Tertiary Alkylamines by Photoredox/Nickel-Catalyzed Aminoalkylation of Organohalides" J. Am. Chem. Soc. 2024, DOI: 10.1021/jacs.4c11602. Tan, T.-D.; Tee, K. Z.; Luo, X.; Qian, P.-C.; Zhang, X.*; Koh, M. J.* "Kinetically-Controlled Z-Alkene Synthesis using Iron-Catalysed Allene Dialkylation" Nat. Synth. 2024, DOI: 10.1038/s44160-024-00658-7. Cong, F.; Ng, J. W.; Koh, M. J.* "A Homolytic Substitution Approach for Directing Group-Free Nickel- Catalyzed Dialkylation of Unactivated Alkenes" Synlett 2024, DOI: 10.1055/a-2352-4902. Jiang, Y.; Wei, Y.; Zhou, Q.-Y.; Sun, G.-Q; Fu, X.-P.; Levin, N.; Zhang, Y.; Liu, W.-Q.; Song, X.; Mohammed, S.; Davis, B. G.*; Koh, M. J.* "Direct Radical Functionalization of Native Sugars" Nature 2024, 631, 319. Xiong, W.; Sun, G.; Zhou, M.; Lu, M.; Koh, M. J.*; Tao, Yang.* "Accessing Fluorinated Tertiary Homoallylamines via Photocatalytic Defluorinative Aminoalkylation of Fluoroalkyl-Substituted Alkenes" ACS Catal. 2024, 14, 8252. Liu, W.-Q.; Lee, B. C.; Song, N.; He, Z.; Shen, Z.-A.; Lu, Y.; Koh, M. J.* "Electrochemical Synthesis of C(sp3)-Rich Amines by Aminative Carbofunctionalization of Carbonyl Compounds" Angew. Chem. Int. Ed. 2024, 63, e202402140. Cong, F.; Sun, G.-Q.; Ye, S.-H.; Hu, R.; Rao, W.; Koh, M. J.* "A Bimolecular Homolytic Substitution-Enabled Platform for Multicomponent Cross-Coupling of Unactivated Alkenes" J. Am. Chem. Soc. 2024, 146, 10274. (Pre-print uploaded on ChemRxiv 2023, DOI: 10.26434/chemrxiv-2023-mpqdw.) (highlighted by SYNFACTS, Synfacts 2024, 20, 708) Luo, X.; Mao, W.; Liu, C.-F.; Wang, Y.-Q.; Nie, J.*; S.-L.*; Jun-An Ma, J.-A.*; Koh, M. J.* "Enantioselective Synthesis of Multifunctional Alkylboronates via N-Heterocyclic Carbene–Nickel-Catalysed Carboboration of Alkenes" Nat. Synth. 2024, 3, 633. (highlighted by SYNFACTS, Synfacts 2024, 20, 594, NUS Science, Phys.org, Today Headline, EurekAlert!) Sun, Q.; Wang, Q.; Qin, W.; Jiang, K; He, G.; Koh, M. J.*; Chen, G.* "N-Glycoside Synthesis through Combined Copper- and Photoredox-Catalysed N-Glycosylation of N-Nucleophiles" Nat. Synth. 2024, 3, 623. Tan, T.-D.; Serviano, J. M. I.; Luo, X.; Qian, P.-C.; Holland, P. L.*; Zhang, X.*; Koh, M. J.* "Congested C(sp3)-rich architectures enabled by iron-catalysed conjunctive alkylation" Nat. Catal. 2024, DOI: 10.1038/s41929-024-01113-8. Lin, L. Q. H.; Rentería-Gómez, Á.; Martin, R. T.; Zhang, Y.-Q.; Ong, K. Z. W.; Parris, A. B.; Gutierrez, O.*; Koh, M. J.* "Selective 1,2- Hydroarylation(alkenylation) of gem-Difluoroalkenes to Access -CF2H Motifs" Angew. Chem. Int. Ed. 2024, 63, e202317935. Wei, Y.; Lin, L. Q. H.; Lee, B. C.; Koh, M. J.* "Recent Advances in First-Row Transition Metal-Catalyzed Reductive Coupling Reactions for π-Bond Functionalization and C-Glycosylation" Acc. Chem. Res. 2023, 56, 3292. (invited review). Wang, Z.-C.; Luo, X.; Zhang, J.-W.; Liu, C.-F.; Koh, M. J.*; Shi, S.-L.* "Enantioselective C–C Cross-Coupling of Unactivated Alkenes" Nat. Catal. 2023, 6, 1087. (highlighted by SYNFACTS, Synfacts 2024, 20, 54, Science Bulletin). Wang, Z.-C.; Zhang, J.-W.; Koh, M. J.*; Shi, S.-L.* "Divergent and Selective Light Alkene Cross-Coupling" Angew. Chem. Int. Ed. 2023, 62, e202310203. Hai, X.; Zheng, Y.; Yu, Q.; Guo, N.; Xi, S.*; Zhao, X.; Mitchell, S.; Luo, X.; Tulus, V.; Wang, M.; Sheng, X.; Ren, L.; Long, X.; Li, J.; He, P.; Lin, H.; Cui, Y.; Peng, X.; Shi, J.; Wu, J.; Zhang, C.; Zou, R.; Guillén-Gosálbez, G.; Pérez-Ramírez, J.*; Koh, M. J.*; Zhu, Y.*; Li, J.*; Lu, J.* "Geminal-Atom Catalysis for Cross-Coupling" Nature 2023, 622, 754. Zhang, W.; Liu, T.; Ang, H T.; Luo, P.; Lei, Z.; Luo, X.; Koh, M. J.*; Jie, W.* "Modular and Practical 1,2-Aryl(alkenyl) Heteroatom Functionalization of Alkenes through Iron/Photoredox Dual Catalysis" Angew. Chem. Int. Ed. 2023, 62, e202310978. (Pre-print uploaded on ChemRxiv 2023, DOI: 10.26434/chemrxiv-2023-gr02g). Jiang, Y.; Zhang, Y.; Lee, B. C.; Koh, M. J.* "Diversification of Glycosyl Compounds via Glycosyl Radicals" Angew. Chem. Int. Ed. 2023, 62, e202305138. (invited Minireview). Lee, B. C.; Liu, C.-F.; Lin, L. Q. H.; Yap, K. Z.; Song, N.; Ko, C. H. M.; Chan, P. H.; Koh, M. J.* "N-Heterocyclic Carbenes as Privileged Ligands for Nickel-Catalysed Alkene Functionalisation" Chem. Soc. Rev. 2023, 52, 2946. Wang, Q.; Lee, B. C.; Song, N.; Koh, M. J.* "Stereoselective C-Aryl Glycosylation by Catalytic Cross-Coupling of Heteroaryl Glycosyl Sulfones" Angew. Chem. Int. Ed. 2023, 62, e202301081. (highlighted by SYNFACTS, Synfacts 2023, 19, 589). Wei, Y.; Wang, Q.*; Koh, M. J.* "A Photoinduced, Nickel-Catalyzed Reaction for the Stereoselective Assembly of C-Linked Glycosides and Glycopeptides" Angew. Chem. Int. Ed. 2023, 62, e202214247. Yang, H.; Xi, S.; Guo, N.; Wang, M.; Liu, L.; Lyu, P.; Yu, X.; Li, J.; Xu, H.; Hai, X.; Li, Z.; Li, X.; Sun, T.; Zhao, X.; Han, Y.; Yu, W.; Wu, J.; Zhang, C.*; Fei, H.*; Koh, M. J.*; Lu, J.* "Catalytically Active Atomically Thin Cuprate with Periodic Cu Single Sites" Natl. Sci. Rev. 2023, 10, nwac100. (highlighted by Phys.org, EurekAlert!) Liu, C.-F.; Wang, Z.-C.; Luo, X.; Lu, J.; Ko, C. H. M.; Shi, S.-L.*; Koh, M. J.* "Synthesis of Tri- and Tetrasubstituted Stereocentres by Nickel-Catalysed Enantioselective Olefin Cross-Couplings" Nat. Catal. 2022, 5, 934. (highlighted by SYNFACTS, Synfacts 2023, 19, 46, NUS Science, Phys.org, X-mol). Jiang, Y.; Yang, K.; Wei, Y.; Wang, Q.*; Li, S.-J.*; Lan, Y.*; Koh, M. J.* "Catalytic Multicomponent Synthesis of C-Acyl Glycosides by Consecutive Cross-Electrophile Couplings" Angew. Chem. Int. Ed. 2022, 61, e202211043. Wang, Q.; Lee, B. C.; Tan, T. J.; Jiang, Y.; Ser, W. H.; Koh, M. J.* "Visible Light Activation Enables Desulfonylative Cross-Coupling of Glycosyl Sulfones" Nat. Synth. 2022, 1, 967. (highlighted by NUS Science, Phys.org, C&EN, X-mol). Chen, Z.; Song, J.; Zhang, R.; Li, R.; Hu, Q.; Wei, P.; Xi, S.; Zhou, X.; Phuc, N. T. T.; Minh, D. H.; Lee, P. S.; Zhao, X.; Koh, M. J.; Yan, N.; Loh, K. P. "Addressing the Quantitative Conversion Bottleneck in Single-Atom Catalysis" Nat. Commun. 2022, 13, 2807. Wang, H.; Koh, M. J.* "Directing Group-Free Approaches for Three-Component Catalytic Dicarbofunctionalization of Unactivated Alkenes" Cell Rep. Phys. Sci. 2022, 3, 100901. (invited perspective). Zhao, Y.; Liu, C.-F.; Lin, L. Q. H.; Chan, A. S. C.*; Koh, M. J.* "Stereoselective Synthesis of Trisubstituted Alkenes by Nickel-Catalyzed Benzylation and Alkene Isomerization" Angew. Chem. Int. Ed. 2022, 61, e202202674. Wang, Q.; Sun, Q.; Jiang, Y.; Zhang, H.; Yu, L.; Tian, C.; Chen, G.*; Koh, M. J.* "Iron-Catalysed Reductive Cross-Coupling of Glycosyl Radicals for the Stereoselective Synthesis of C-Glycosides" Nat. Synth. 2022, 1, 235. Huang, L.; Lim, E. Q.; Koh, M. J.* "Secondary Phosphine Oxide-Activated Nickel Catalysts for Site-Selective Alkene Isomerization and Remote Hydrophosphination" Chem Catal. 2022, 2, 508. (Pre-print uploaded on ChemRxiv 2021, DOI: 10.33774/chemrxiv-2021-cld3z.) Wang, H.; Liu, C.-F.; Tan, T.-D.; Khoo, K. R. B.; Koh, M. J.* "N-Heterocyclic Carbene–Nickel-Catalyzed Regioselective Diarylation of Aliphatic-1,3-Dienes" ACS Catal. 2022, 12, 724. Wang, H.; Liu, C.-F.; Martin, R. T.; Gutierrez, O.*; Koh, M. J.* "Directing Group-Free Catalytic Dicarbofunctionalization of Unactivated Alkenes" Nat. Chem. 2022, 14, 188. (highlighted by SYNFACTS, Synfacts 2022, 18, 323, NUS Science, Phys.org, C&EN, X-mol) i, P.; Lee, B. C.; Zhang, X.; Koh, M. J.* "Base-Mediated Site-Selective Hydroamination of Alkenes" Synthesis 2022, 54, 1566. (invited feature article). (highlighted by Organic Chemistry Portal). Chen, Z.; Liu, J.; Koh, M. J.; Loh, K. P. "Single-Atom Catalysis: From Simple Reactions to the Synthesis of Complex Molecules" Adv. Mater. 2022, 34, 2103882. Liu, J.; Chen, Z.; Koh, M. J.; Loh, K. P. "Deuterium labelling by electrochemical splitting of heavy water" Energy Mater. 2021, 1, 100016. Jiang, Y.; Wang, Q.*; Zhang, X.*; Koh, M. J.* "Synthesis of C-Glycosides by Ti-Catalyzed Stereoselective Glycosyl Radical Functionalization" Chem 2021, 7, 3377. (highlighted by NUS Science, Phys.org). Yoon, J.; Grinchuk, O. V.; Kannan, S.; Ang, M. J. Y.; Li, Z.; Tay, E. X. Y.; Lok, K. Z.; Lee, B. W. L; Chuah, Y. H.; Chia, K.; Magallanes, R. T.; Liu, C.-F.; Zhao, H.; Hor, J. H.; Lim, J. J.; Benoukraf, T.; Toh, T. B.; Chow, E. K.-H.; Kovalik, J.-P.; Ching, J.; Ng, S.-Y.; Koh, M. J.; Liu, X.; Verma, C. S.; Ong, D. S. T. "A Chemical Biology Approach Reveals a Dependency of Glioblastoma on Biotin Distribution" Sci. Adv. 2021, 7, eabf6033. Liu, C.-F.; Wang, H.; Martin, R. T.; Zhao, H.; Gutierrez, O.*; Koh, M. J.* "Olefin Functionalization/Isomerization Enables Stereoselective Alkene Synthesis" Nat. Catal. 2021, 4, 674. (highlighted by NUS Science, Phys.org, X-mol). Chen, C.; Ou, W.; Yam, K.-M. Xi, S.; Zhao, X.; Chen, S.; Li, J.; Lyu, P.; Ma, L.; Du, Y.; Yu, W.; Fang, H.; Yao, C.; Hai, X.; Xu, H.; Koh, M. J.; Pennycook, S. J.; Lu, J.; Lin, M.; Su, C.; Zhang, C.; Lu, J. "Zero-Valent Palladium Single-Atoms Catalysts Confined in Black Phosphorus for Efficient Semi-Hydrogenation" Adv. Mater. 2021, 33, 2008471. Chen, Z.; Song, J.; Peng, X.; Xi, S.; Liu, J.; Zhou, W.; Li, R.; Ge, R.; Liu, C.; Xu, H.; Zhao, X.; Li, H.; Zhou, X.; Wang, W.; Li, X.; Zhong, L.; Rykov, A. I.; Wang, J.; Koh, M. J.; Loh, K. P. "Iron Single Atom Catalyzed Quinoline Synthesis" Adv. Mater. 2021, 33, 2101382. Liu, C.-F.; Luo, X.; Wang, H.*; Koh, M. J.* "Catalytic Regioselective Olefin Hydroarylation(alkenylation) by Sequential Carbonickelation-Hydride Transfer" J. Am. Chem. Soc. 2021, 143, 9498. (highlighted by Organic Chemistry Portal). Yang, T.; Wei, Y.; Koh, M. J.* "Photoinduced Nickel-Catalyzed Deaminative Cross-Electrophile Coupling for C(sp2)–C(sp3) and C(sp3)–C(sp3) Bond Formation" ACS Catal. 2021, 11, 6519. Liu, J.; Chen, Z.; Liu, C.; Zhang, B.; Du, Y.; Liu, C.-F.; Ma, L.; Xi, S.; Li, R.; Zhao, X.; Song, J.; Sui, X. Z.; Yu, W.; Miao, L.*; Jiang, J.; Koh, M. J.*; Loh, K. P.* "Molecular Engineered Palladium Single Atom Catalysts with an M-C1N3 Subunit for Suzuki Coupling" J. Mater. Chem. A 2021, 9, 11427. Telychko, M.; Li, G.; Mutombo, P.; Soler-Polo, D.; Peng, X.; Su, J.; Song, S.; Koh, M. J.; Edmonds, M.; Jelinek, P.; Wu, J.; Lu, J. "Ultra-high Yield On-surface Synthesis and Assembly of Circumcoronene into Chiral Electronic Kagome-honeycomb Lattice" Sci. Adv. 2021, 7, eabf0269. Jiang, Y.; Pan, J.; Yang, T.; Zhao, Y.*; Koh, M. J.* "Nickel-Catalyzed Site- and Stereoselective Reductive Alkylalkynylation of Alkynes" Chem 2021, 7, 993. Yu, X.; Zheng, H.; Zhao, H.; Lee, B. C.; Koh, M. J.* "Iron‐Catalyzed Regioselective Alkenylboration of Olefins" Angew. Chem. Int. Ed. 2021, 60, 2104. (highlighted by SYNFACTS, Synfacts 2021, 17, 160). Yang, T.; Jiang, Y.; Luo, Y.; Lim, J. J. H.; Lan, Y.*; Koh, M. J.* "Chemoselective Union of Olefins, Organohalides and Redox-Active Esters Enables Regioselective Alkene Dialkylation" J. Am. Chem. Soc. 2020, 142, 21410. (Pre-print uploaded on ChemRxiv 2020, DOI: 10.26434/chemrxiv.13114625.) (highlighted by X-mol, Organic Chemistry Portal). Chen, X.; Rao, W.; Yang, T.*; Koh, M. J.* "Alkyl Halides as Both Hydride and Alkyl Sources in Catalytic Regioselective Reductive Olefin Hydroalkylation" Nat. Commun. 2020, 11, 5857. (Pre-print uploaded on ChemRxiv 2020, DOI: 10.26434/chemrxiv.12675368.) (highlighted by SYNFACTS, Synfacts 2021, 17, 185). Yu, X.; Zhao, H.; Koh, M. J.* "Site-Selective Remote Protoboration by Fe Catalysis" Trends Chem. 2020, 2, 1141. Yu, X.; Zhao, H.; Li, P.; Koh, M. J.* "Iron-Catalyzed Tunable and Site-Selective Olefin Transposition" J. Am. Chem. Soc. 2020, 142, 18223. (highlighted by NUS Science, Phys.org, AZoM, Chem-Station). Song, S.; Guo, N.; Li, X.; Li, G.; Haketa, Y.; Telychko, M.; Su, J.; Lyu, P.; Qiu, Z.; Fang, H.; Peng, X.; Li, J.; Wu, X.; Li, Y.; Su, C.; Koh, M. J.; Wu, J.; Maeda, H.; Zhang, C.; Lu, J. "Real-Space Imaging of a Single-Molecule Monoradical Reaction" J. Am. Chem. Soc. 2020, 142, 13550. Yu, X.; Zhao, H.; Xi, S.; Chen, Z.; Wang, X.; Wang, L.; Lin, L. Q. H.; Loh, K. P.; Koh, M. J.* "Site-Selective Alkene Borylation Enabled by Synergistic Hydrometallation and Borometallation" Nat. Catal. 2020, 3, 585. (highlighted by NUS Science, Phys.org, X-mol). Wang, H.; Liu, C.-F.; Song, Z.; Yuan, M.; Ho, Y. A.; Gutierrez, O.*; Koh, M. J.* "Engaging α-Fluorocarboxylic Acids Directly in Decarboxylative C-C Bond Formation" ACS Catal. 2020, 10, 4451. (highlighted by Chemistry World). Yang, T.; Chen, X.; Rao, W.; Koh, M. J.* "Broadly Applicable Directed Catalytic Reductive Difunctionalization of Alkenyl Carbonyl Compounds" Chem 2020, 6, 738. Chen, Z.; Liu, C.; Liu, J.; Li, J.; Xi, S.; Chi, X.; Xu, H.; Park, I.-H.; Peng, X.; Li, X.; Yu, W.; Liu, X.; Zhong, L.; Leng, K.; Huang, W.; Koh, M. J.*; Loh, K. P.* "Cobalt Single-Atom-Intercalated Molybdenum Disulfide for Sulfide Oxidation with Exceptional Chemoselectivity" Adv. Mater. 2020, 32, 1906437. Telychko, M.; Su, J.; Gallardo, A.; Gu, Y.; Mendieta-Moreno, J. I.; Qi, D.; Tadich, A.; Song, S.; Lyu, P.; Qiu, Z.; Fang, H.; Koh, M. J.; Wu, J.; Jelínek, P.; Jiong, L. "Strain‐Induced Isomerization in One‐Dimensional Metal–Organic Chains" Angew. Chem. Int. Ed. 2019, 131, 18764. Liu, C.; Chen, Z.; Yan, H.; Yam, K. M.; Gao, J.; Du, Y.; Xi, S.; Li, J.; Zhao, X.; Xu, H.; Li, X.; Fu, W.; Leng, K.; Xie, K.; Pennycook, S. J.; Liu, B.; Zhang, C.; Koh, M. J.*; Loh, K. P.* "Expedient Synthesis of E-Hydrazone Esters and 1H-Indazole Scaffolds through Heterogeneous Single-Atom Platinum Catalysis" Sci. Adv. 2019, 5, eaay1537. (highlighted by SYNFORM).