Shi, Xiaodong Michael - University of South Florida

个人简介

Education 1990-1994 BS, Department of Chemistry, Nankai University, China 1994-1997 MS, Department of Chemistry, Nankai University, China 1998-2002 Ph.D. Departme of Chemistry, University of Maryland, College Park Mentor: Professor Jeffery T. Davis 2002-2005 Postdoc Research Associate, Departme of Chemistry, University of California Berkeley Mentors: Professor Paul Bartlett, Professor F. Dean Toste Appointments 2005 General Electric, Research Scientist 2005-2015 Assistant, Associate, Full Professor, Department of Chemistry, West Virginia University 2015-2017 Associate Professor, Department of Chemistry, University of South Florida 2017-present Professor, Department of Chemistry, University of South Florida

研究领域

Methodology Development Attracted by the unique properties of 1,2,3-triazole, our group developed a series of synthetic and functionalization methods of 1,2,3-triazoles.Â With these practical synthetic methods, we were able to explore several metal complexes utilizing triazole as the ligand, such as Au, Rh, Pd and Ir, which showed different reactivities compared with conventional ligands. We are now focusing on new methodology development based on triazole-metal catalysts and the “why” behind the “how”. Asymmetric Catalysis Ligand design based on 1,2,3-triazole skeleton for asymmetric catalysis is another interest of our group.Â Taking advantage of the unique binding properties and easy synthesis of various triazole derivatives, it is promising that we will develop some efficient chiral ligands. New Material Development Azaborines are interesting new materials since the B-N bond is isoelectronic with a C-C double bond.Â Based on the excellent stability and chemoselectivity of triazole-gold catalyst, new synthetic method for aza-borane was achieved in our group and will be further developed. By cooperation with Prof. Shengqian Ma, various triazole-based MOF material were synthesized and characterized.Â Along with that, we will also develop MOF catalysts based on triazole-skeleton. Bioorganic Chemistry Another inspiring feature of 1,2,3-triazole is the excellent biocompatibility.Â With that in mind, we developed a series of triazole derivatives and applied them sucessfully as fluorophores or anti-cancer drugs.Â We are also interested in target-oriented synthesis and application of these molecules in vivo.

近期论文

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Yuan, T., Radefeld, K., Shan, C., Wegner, C., Nichols, E., Ye, X., Tang, Q., Wojtas L., Shi, X.*"Asymmetric Hydrative Aldol Reaction (HAR) via Vinyl-Gold Promoted Intermolecular Ynamide Addition to Aldehydes." Angew. Chem. Int. Ed. 2023, e202305810. Wei, J., Xing, Y., Ye, X., Nguyen, B., Wojta,s L., Hong, X., Shi, X.*" Gold-Catalyzed Amine Cascade Addition to Diyne-Ene: Enantioselective Synthesis of 1,2-Dihydropyridines." Angew. Chem. Int. Ed. 2023, e202305409. Zhang, S., Shi, X.*" A gold oxidation relay." Nat. Synth, 2023, 2, 313-314. Wei, J.; Liu, M.; Ye, X.; Zhang, S.; Sun, E.;Shan, C; Wojtas, L.; ;Shi, X.*"Facile synthesis of diverse hetero polyaromatic hydrocarbons (PAHs) via the styryl Diels-Alder reaction of conjugated diynes"Org. Chem. Front., 2022, 9, 4301-4308. Qi, T.; Li, S.; Ye, X.; Teng, Y.; Zhao, K.; He,Y.; Shan, C.; Wojtas, L.; Richardson, D., Lan, Y.*; Shi, X.*"Design and Synthesis of Stable Four-Coordinated Benzotriazole-Borane with Tunable Fluorescence Emission" Chem. Sci., 2022, 13, 5982. Ye,X.; Wang, C.; Zhang, S.; Qi, T.; Wojtas, L.; Li, M.*;Shi, X.*"Chiral Hemilabile P,N-Ligands Assisted Gold Redox Catalysis for Enantioselective Alkene Aminoarylation"Chem. Eur. J., 28, e202201018. Wang, Z.; Ye, X.; Jin, M.; Tang, Q.; Fan, S.; Song, Z.*; Shi, X.*"4-Aminobenzotriazole (ABTA) as a Removable Directing Group for Palladium-Catalyzed Aerobic Oxidative Câ€“H Olefination" Org. Lett. 2022, 24, 3107. He, Y.; Liu, M.; Teng, S.; Wojtas, L.; Gu, G.; Shi, X.*"Synthesis and characterization of fluorescence active G4-quartet and direct evaluation of self-assembly impact on emission" Chin. Chem. Lett. 2022, 03, 007. Dong, G.; Ye, X.; Wang, S.; Li, W.; Cai, R.; Du, L.; Shi, X*.; Li, M*."Au-24 as a potential thioredoxin reductase inhibitor in hepatocellular carcinoma cells" Pharmacol. Res. 2022,106113. Li, J.; He, Y.; Zou, Y.; Yan Y.; Song, Z.; Shi, X*. "Achieving a stable COF with the combination of flat and twist large-size rigid synthons for selective gas adsorption and separation" Chin. Chem. Lett. 2021,12, 001. He, Y.; Zhang, Y.; Liu, M.; Zhao, K.; Shan, C.; Wojtas, L.; Guo, H.; Ding, A.; Shi, X.* "Synthesis of microporous hydrogen-bonded supramolecular organic frameworks through guanosine self-assembly" Cell Rep. Phys. Sci. 2021, 2, 100519. Jia, T.; Fan, S.; Li, F.; Ye, X.; Zhang, W.; Song, Z.*; Shi, X.* "Achieving Aliphatic Amine Addition to Arylalkynes via the Lewis Acid Assisted Triazole-Gold (TA-Au) Catalyst System" Org. Lett. 2021, 23, 6019-6023. Zhao, K.; He, Y.; Shan, C.; Wojtas, L.; Ren, J.; Yan, Y.; Shi, H.; Wang, H.; Song, Z.*; Shi, X.* "Construction of Stable Helical Metal-Organic Frameworks with Conformationally Rigid "Concave Ligand" Chem. Eur. J. 2021, 27, 10833-10838. Liu, M.; He, Y.; Shan, C.; Wojtas, L.; Ghiviriga, I.; Fathalla, O.; Yan, Y.; Li, X.; Shi, X.* "Anion Mediated, Tunable Isoguanosine Self-Assemblies: Decoding the Conformation Influence and Solvent Effect" Chem. Sci. 2021, 12, 7569-7574. Yuan, T.; Tang, Q.; Shan, C.; Ye, X.; Wang, J.; Zhao, P.; Wojtas, L.; Hadler, N.; Chen, H.; Shi, X.* "Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining pi-Acid Activation, Vinyl-Gold Addition, and Redox Catalysis" J. Am. Chem. Soc. 2021, 143, 4074-4082. Zhang, S.; Ye, X.; Wojtas, L.; Hao, W.; Shi, X.* "Electrochemical gold redox catalysis for selective oxidative arylation" Green Syn. & Catal. 2021, 2, 82-86. Wang, Y.; Zheng, L.; Shi, X.* and Chen, Y. "1,3-Difunctionalization of B-Alkyl Nitroalkenes via Combination of Lewis Base Catalysis and Radical Oxidation" Org. Lett. 2021, 23, 886-889. Li, J.; He, Y.; Wang, L.; Li, G.; Zou, Y.; Yan, Y.; Li, D.; Shi, X.; Song, Z.; Shi, X. "Construction of fluorescence active MOFs with symmetrical and conformationally rigid N-2-aryl-triazole ligands" RSC Adv. 2020, 10, 41921-41925. Zhang, Y.; He, Y.; Wojtas, L.; Shi, X.*; Guo, H.* "Construction of Supramolecular Organogel with Circularly Polarized Luminescence by Self-Assembled Guanosine Octamer" Cell Rep. Phys. Sci. 2020, 1, 100211. Li, Z.; Lin, Y.; Song, H.; Qin, X.; Yu, Z.; Zhang, Z.; Dong, G.; Li, X.; Shi, X.; Du, L.; Zhao, W.; Li, M. "First small-molecule PROTACs for G protein-coupled receptors: inducing a1A-adrenergic receptor degradation" Acta Pharm. Sin. B 2020, 10, 1669-1679. Zhao, K.; He, Y.; Shan, C.; Ren, J.; Wojtas, L.; Wang, L.; Li, G.; Song, Z.*; Shi, X.* ""Orthogonal-Twisted-Arm" Ligands for The Construction of Metal-Organic Frameworks: New Topology and Catalytic Reactivity" Chem. Eur. J. 2020, 26, 16272-16276. Zhang, X.; Ren, G.*; He, Z.; Yang, W.; Li, H.; Wang, Y.; Pan, Q.*; Shi, X.* "Luminescent detection of Cr(VI) and Mn(VII) based on a stable supramolecular organic framework" Cryst. Growth Des. 2020, 20, 6888-6895. Ye, X.; Wang, C.; Zhang, S.; Wei, J.; Shan, C.; Wojtas, L.; Xie, Y.; Shi, X.* "Facilitating Ir-Catalyzed C-H Alkynylation with Electrochemistry: Anodic Oxidation Induced Reductive Elimination" ACS Catal. 2020, 10, 11693-11699. Zhang, S.; Wang, C.; Ye, X.; Shi, X.* "Intermolecular Alkene Difunctionalization via Gold Catalyzed Oxyarylation" Angew. Chem. Int. Ed. 2020, 59, 20470 - 20474. Wei, C.; He, Y.; Wang, J.; Ye, X.; Wojtas, L.; Shi, X.* "Hexafluoroisopropanol-Promoted Disulfidation and Diselenation of Alkyne, Alkene, and Allene." Org. Lett., 2020, 22, 5462-5465. Li, X.; Ye, X.; Wei, C.; Shan, C.; Wojtas, L.; Wang, Q.*; Shi, X.* "Diazo Activation with Diazonium Salts: Synthesis of Indazole and 1,2,4-Triazole." Org. Lett., 2020, 22, 4151-4155. Yuan, T.; Ye, X.; Zhao, P.; Teng, S.; Yi, Y.; Wang, J.; Shan, C.; Wojtas, L.; Jean, J.; Chen, H.; Shi, X.* "Regioselective Crossed Aldol Reactions under Mild Conditions via Synergistic Gold-Iron Catalysis." Chem, 2020, 6, 1420-1431. Li, J.; He, Y.; Wang, L.; Pan, Q. H.; Song, Z.; Shi, X.* "Design and Synthesis of Photoluminescent Active Interpenetrating Metal-Organic Frameworks Using N-2-Aryl-1,2,3-Triazole Ligands." Dalton Trans., 2020, 49, 5429-5433. Wang, J.; Wei, C.; Li, X.; Zhao, P.; Shan, C.; Wojtas, L.; Chen, H.; Shi, X.* "Gold Redox Catalysis with a Selenium Cation as Mild Oxidant." Chem. Eur. J. 2020, 26, 5946-5950. He, Y.; Zhang, Y.; Wojtas, L.; Akhmedov, N.; Pan, Q.; Guo, H.; Shi, X.* “Reversed Cation Selectivity of G8-Octamer and G16-Hexadecamer towards Monovalent and Divalent Cations” Chem. Asian J. 2020, 15, 1030-1034. Qin, X.; Ma, Z.; Yang, X.; Hu, S.; Chen, X.; Liang, D.; Lin, X.; Shi, X.; Du, L.; Li, M.* “Discovery of Environment-Sensitive Fluorescent Agonists for a1-Adrenergic Receptors” Anal. Chem. 2019, 91, 12173-12180. Peng, X.; Hu, Z.; Zhang, J.; Ning, W.; Zhang, S.; Doing, C.; Shi, X.*; Zhou, H.* “Construction of benzofuranone library via a metal-free, one-pot intermolecular condensation, and their application as efficient estrogen receptor Î² modulators” Chem. Commun. 2019, 55, 14570-14573. Ye, X.; Zhao, P.; Zhang, S.; Zhang, Y.; Wang, Q.; Shan, C.; Wojtas, X.; Guo, H.*; Chen, H.*; Shi, X.* “Facilitating Gold Redox Catalysis with Electrochemistry: An Efficient Chemical-Oxidant-Free Approach” Angew. Chem. Int. Ed. 2019, 58, 17226-17230. This paper has been highlighted by Synfacts, 2020, 16, 172. Jimoh, A.; Hosseyni, S.; Ye, X.; Wojtas, L.; Hu, Y.*; Shi, X.* “Gold redox catalysis for cyclization/arylation of allylic oximes: synthesis of isoxazoline derivatives” Chem. Commun. 2019, 55, 8150-8153. Wei, C.; Ye, X.; Xing, Q.; Hu, Y.;* Xie, Y.;* Shi, X.* “Synergistic palladium/enamine catalysis for asymmetric hydrocarbon functionalization of unactivated alkenes with ketones” Org. Biomol. Chem. 2019, 17, 6607-6611. He, Y.; Zhang, Y.; Wojtas, L.; Akhmedov, N. G.; Thai, D.; Wang, H.; Li, X.; Guo, H.*; Shi, X.* “Construction of a cross-layer linked G-octamer via conformational control: a stable G-quadruplex in H-bond competitive solvents” Chem. Sci. 2019, 10, 4192-4199. Lai, Q.; Liu, Q.; Zhao, K.; Shan, C.; Wojtas, L.; Zheng, Q.; Shi, X.;* Song, Z.* “Rational design and synthesis of yellow-light emitting triazole fluorophores with AIE and mechanochromic properties” Chem. Commun. 2019, 55, 4603-4606. Wei, C.; He, Y.; Shi, X.;* Song, Z.* “Terpyridine-Metal Complexes: Applications in catalysis and supramolecular chemistry” Coordin. Chem. Rev. 2019, 385, 1-19. Lai, Q.; Liu, Q.; He, Y.; Zhao, K.; Wei, C.; Wojtas, L.; Shi, X.;* Song, Z.* “Triazole-imidazole (TA-IM) derivatives as ultrafast fluorescent probes for selective Ag+ detection” Org. Biomol. Chem. 2018, 16, 7801. Li, P.; Zhao, J.; Shi, L.; Wang, J.; Shi, X.;* Li, F.* “Iodine Catalyzed Diazo Activation to Access Radical Reactivity” Nature Commun. 2018, 9, 1972. Ye, X.; Peng, H.; Wei, C.; Teng, Y.; Wojtas, L.; Shi, X.;* “Gold-Catalyzed Oxidative Coupling of Alkynes towards the Synthesis of Cyclic Conjugated Diynes” Chem 2018, 4, 1983-1993. Zhang, F.; Lai, Q.; Shi, X.;* Song, Z.* “Triazole-Gold (TA-Au) Catalyzed Three-Component Coupling (A3 reaction) towards the Synthesis of 2,4-Disubstituted Quinoline Derivatives” Chin. Chem. Lett. 2019, 30, 392-394. Wang, J.; Zhang, S.; Xu, C.; Wojtas, L,; Akhmedov, N. G.; Chen, H.;* Shi, X.* “Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need of a Strong Oxidant” Angew. Chem. Int. Ed. 2018, 57, 6915-6920. Motika, S. E.; Shi, X.* “Synthesis and Application of a Novel Bis-1,2,3-Triazole Ligand Containing a 2,2'-Bipyrrolidine Core” Arkivoc 2018, 280-287. Lei, X.; Zheng, L.; Zhang, C.; Shi, X.;* Chen, Y.* “Allylic C-S Bond Construction through Metal-Free Direct Nitroalkene Sulfonation” J. Org. Chem. 2018, 83, 1772-1778. Lu, M.; Su, Y.; Zhao, P.; Ye, X.; Cai, Y.; Shi, X.;* Masson, E.;* Li, F.; Campbell, J. L.; Chen, H.* “Direct Evidence for the Origin of Bis-Gold Intermediates: Probing Gold Catalysis with Mass Spectrometry” Chem. Eur. J. 2018, 24, 2144-2150.