Studer, Armido - Westfälische Wilhelms-Universität Münster

个人简介

since 11/2009 Full Professor (W3) of Organic Chemistry at the Organisch-Chemisches Institut, WWU Münster, Germany. 2004 - 2009 Full Professor (C4) of Organic Chemistry at the Organisch-Chemisches Institut, WWU Münster, Germany. 2000 - 2004 Associate Professor of Organic Chemistry at the Philipps-Universität Marburg, Germany. 1996 - 2000 Independent research on the development of new synthetic methods in the field of free radical chemistry. "Habilitation" at the Laboratorium für Organische Chemie, ETH Zürich (October 2000). 1995 - 1996 Postdoctoral Studies at the University of Pittsburgh (USA) in the group of Prof. Dr. D. P. Curran. 1992 - 1995 PhD student at the ETH Zürich (SUI) under the guidance of Prof. Dr. D. Seebach (New Applications of 2-tert-Butylimidazolidinones in Asymmetric Synthesis). 1987 - 1991 Studies in chemistry at the ETH Zürich, CH. Diploma thesis in the research group of Prof. Dr. D. Seebach (Synthesis of Novel Tripeptides).

研究领域

Radical Chemistry in Organic Synthesis – Method Development In organic synthesis selective bond forming reactions via C-centered radicals have become valuable tools for construction of complex systems. Carboaminoxylation, base promoted homolytic aromatic substitution and novel heteroatom radical precursors improve the general applicability of radical chemistry in organic synthesis. The Studer group is interested in the development of efficient oxidative C-C and C-X bond forming reactions by using nitroxides as mild oxidants. These methods allow for stereoselective vicinal bisfunctionalization of unactivated alkenes. Radicals and Catalysis As compared to non-radical processes, most radical reactions are fast. Radical reactions require only a small amount of initiator, addition of a catalyst is generally not necessary. The Studer group is working on catalytic processes, where radicals or radical ions occur as intermediates. The group has pioneered the field of oxidative carbene catalysis, where acyl azolium ions as intermediates allow for highly stereoselective cascade reactions. Novel strategies for transition metal catalyzed processes using radicals as oxidants have been established. Several observations have shown that radicals are involved in a series of transition metal mediated transformations. The novel concept of the electron as an efficient catalyst for conducting various types of radical cascade reactions is currently explored. Systems Chemistry –Organic Chemistry at Interfaces and in Hybrid Materials The basic knowledge gathered by the Studer group on synthetic radical chemistry is also successfully used in neighboring disciplines. For example the laboratory has significantly contributed to the field of Nitroxide Mediated controlled radical Polymerization (NMP). These activities have opened the door to a broader view on materials and to the application of organic transformations in meso scale systems. Moreover, with these lessons learned, the group is currently developing novel methods to chemically construct and modify molecular assemblies at the nano level in solution as well as at interfaces.

近期论文

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Skeletal editing of pyridines through atom-pair swap from CN to CC,Q. Cheng, D. Bhattacharya, M. Haring, H. Cao, C. Mück-Lichtenfeld, A. Studer,Nat. Chem. 2024, accepted. [doi:10.1038/s41557-023-01428-2] Borylative transition metal-free couplings of vinyl iodides with various nucleophiles, alkenes or alkynes,G. Seidler, M. Schwenzer, F. Clausen, C. G. Daniliuc, A. Studer,Chem. Sci. 2024, accepted. [doi:10.1039/D3SC06131K] Benzoyldiisopropylchlorosilane: a visible light photocleavable alcohol protecting group,F. Lind, K. Markelov, A. Studer,Chem. Sci. 2023, 14, 12615-12620. [doi:10.1039/D3SC04975B] Cooperative Photoredox and N-Heterocyclic Carbene Catalyzed Fluoroaroylation for the Synthesis of α-Trifluoromethyl-Substituted Ketones,X. Yu, A. Maity, A. Studer,Angew. Chem. Int. Ed. 2023, 62, e202310288. [doi:10.1002/anie.202310288] Access to Polyheterocyclic Compounds through Iron(II)-Mediated Radical Cascade Cyclization Utilizing 2-Ethynylbenzaldehydes and Aryl Isonitriles,S. K. Banjare, D. Leifert, F. Weidlich, C. G. Daniliuc, F. A. Alasmary, A. Studer,Org. Lett. 2023, 25, 6424-6428. [doi:10.1021/acs.orglett.3c02448] Organic Synthesis Using Nitroxides,D. Leifert, A. Studer,Chem. Rev. 2023, 123, 10302-10380. [doi:10.1021/acs.chemrev.3c00212] Aminoacylation of Alkenes by Cooperative NHC and Photoredox Catalysis,L. Lezius, J. Reimler, N. Döben, M. Hamm, C. G. Daniliuc, A. Studer,Synlett 2023, 34, accepted. [doi:10.1055/a-2145-8697] C–H Functionalization of Pyridines via Oxazino Pyridine Intermediates: Switching to para-Selectivity under Acidic Conditions,H. Cao, D. Bhattacharya, Q. Cheng, A. Studer, J. Am. Chem. Soc. 2023, accepted. [doi:10.1021/jacs.3c05242] Photocatalytic phosphine-mediated water activation for radical hydrogenation, J. Zhang, C. Mück-Lichtenfeld, A. Studer, Nature 2023, accepted. [doi:10.1038/s41586-023-06141-1] 1,2-Aminoxyalkylation of Alkenes with Alkyl Iodides and TEMPONa through SET- and XAT-Processes,A. Maity, A. Studer, Chem. Sci. 2023, 14, accepted. [doi:10.1039/D3SC02544F] Lewis Acid Catalyzed Formal (3+2)-Cycloaddition of Bicyclo[1.1.0]butanes with Ketenes, N. Radhoff, C. G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 2023, 62, e202304771. [doi:10.1002/anie.202304771] Regioselective Formal β-Allylation of Carbonyl Compounds Enabled by Cooperative Nickel and Photoredox Catalysis, K. Liu, Z. Wang, A. N. Künzel, M. Layh, A. Studer, Angew. Chem. Int. Ed. 2023, 62, e202303473. [doi:10.1002/anie.202303473] Intramolecular Radical Oxygen-Transfer Reactions Using Nitroarenes, J. Elfert, A. Bhunia, C. G. Daniliuc, A. Studer,ACS Catal. 2023, 13, 6704-6709. [doi:10.1021/acscatal.3c00958] Regiodivergent C−H Acylation of Arenes by Switching from Ionic to Radical Type Chemistry Using NHC-Catalysis, J. Reimler, X.-Y. Yu, N. Spreckelmeyer, C. G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 2023, 62, e202303222. [doi:10.1002/anie.202303222] Alkyl Radical Generation from Alkylboronic Pinacol Esters through Substitution with Aminyl Radicals, Z. Wang, N. Wierich, J. Zhang, C. G. Daniliuc, A. Studer, J. Am. Chem. Soc. 2023, 145, accepted. [doi:10.1021/jacs.3c01129] Rhodium-Catalyzed Hydrosilylation of Alkenes with Acylhydrosilanes,F. Lind, A. Studer, Chem. Eur. J. 2023, 29, e202301120. [doi:10.1002/chem.202301120] Enantioselective Copper-Catalyzed Fukuyama Indole Synthesis from 2-Vinylphenyl Isocyanides,T. Drennhaus, D. Leifert, J. Lammert, J. P. Drennhaus, K. Bergander, C. G. Daniliuc, A. Studer, J. Am. Chem. Soc. 2023, 145, 8665-8676. [doi:10.1021/jacs.3c01667] meta-Selective C−H Functionalization of Pyridines,H. Cao, Q. Cheng, A. Studer, Angew. Chem. Int. Ed. 2023, 62, e202302941. [doi:10.1002/anie.202302941] Highly Selective On-Surface Reactions of Aryl Propiolic Acids via Decarboxylative Coupling,H. Kong, L. Viergutz, L. Liu, A. Sandvoß, X. Peng, H. Klaasen, H. Fuchs, A. Studer, Adv. Mater. 2023, 35, 2210997. [doi:10.1002/adma.202210997] Bis(arylsulfonyl) Peroxide-Mediated Difunctionalization of Cyclic Enol Ethers,R. O. McCourt, A. Studer, J. Org. Chem. 2023, 88, 1860-1864. [doi:10.1021/acs.joc.2c02541] Iodine-Induced Self-Assembly Structure Transition of Organic Molecules on the Ag(111) Surface, Y. Wang, K. Ma, T. Zhang, P. A. Held, A. Studer, H. Fuchs, Z. Hu, Z. Sun, Y. Han, H.-Y. Gao, J. Phys. Chem. C 2023, 127, 1381-1387. [doi:10.1021/acs.jpcc.2c06589] Radical and ionic meta-C–H functionalization of pyridines, quinolines, and isoquinolines,H. Cao, Q. Cheng, A. Studer,Science 2022, 378, 779-785. [doi:10.1126/science.ade6029]; Visible-Light-Mediated Radical Silyl-Oximation of Activated Alkenes Using tert-Butyl Nitrite and Silanes,S. Plöger, A. Studer, Org. Lett. 2022, 24, 8568-8572. [doi:10.1021/acs.orglett.2c03644] Radical NHC Catalysis, K. Liu, M. Schwenzer, A. Studer,ACS Catal. 2022, 12, 11984-11999. [doi:10.1021/acscatal.2c03996] Synthesis of 5-Membered Ring Systems Bearing gem-Difluoroalkenyl and Monofluoroalkenyl Substituents via Radical β-Bromo Fragmentation,P. Xu, C. G. Daniliuc, K. Bergander, C. Stein, A. Studer,ACS Catal. 2022, 12, 11934-11941. [doi:10.1021/acscatal.2c03775] Oxy-Borylenes as Photoreductants: Synthesis and Application in Dehalogenation and Detosylation Reactions,P. Lenz, R. Oshimizu, S. Klabunde, C. G. Daniliuc, C. Mück-Lichtenfeld, J. C. Tendyck, T. Mori, W. Uhl, M. R. Hansen, H. Eckert, S. Yamaguchi, A. Studer, Angew. Chem. Int. Ed. 2022, 61, e202209391. [doi:10.1002/anie.202209391] Azodioxy Compounds as Precursors for C-Radicals and Their Application in Thermal Styrene Difunctionalization,S. Plöger, C. Mück-Lichtenfeld, C. G. Daniliuc, A. Studer, Chem. Sci. 2022, 13, 9749-9754. [doi:10.1039/D2SC03860A] Cooperative NHC/Photoredox Catalysis: Three Component Radical Coupling of AroylFluorides, Styrenes and Alcohols, N. Döben, J. Reimler, A. Studer, Adv. Synth. Catal. 2022, 364, 3348-3353. [doi:10.1002/adsc.202200574] Oxidative NHC-catalyzed Intramolecular Friedel-Crafts-Alkylation of Indoles for the Synthesis of Spirocyclic Indolenines, C. B. J. Breuers, C. G. Daniliuc, A. Studer, Org. Lett. 2022, 24, 5314-5318. [doi:10.1021/acs.orglett.2c01927] Cooperative triple catalysis enables regioirregular formal Mizoroki–Heck reactions, K. Liu, D. Leifert, A. Studer, Nat. Synth. 2022, 6, 565–575. [doi:10.1038/s44160-022-00101-9] Decatungstate-catalyzed radical disulfuration through direct C-H functionalization for the preparation of unsymmetrical disulfides, J. Zhang, A. Studer, Nat. Commun. 2022, 13, 3886. [doi:10.1038/s41467-022-31617-5]; Dearomatizing Cyclization of 2-Iodoindoles by Oxidative NHC Catalysis to Access Spirocyclic Indolenines and Oxindoles Bearing an All Carbon Quaternary Stereocenter, C. B. J. Breuers, C. G. Daniliuc, A. Studer, Org. Lett. 2022, 24, 4960-4964. [doi:10.1021/acs.orglett.2c01851] Formal β-C-H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis, K. Liu, A. Studer, Angew. Chem. Int. Ed. 2022, 61, e202206533. [doi:10.1002/anie.202206533] 1,4-Aryl migration in ketene-derived enolates by a polar-radical-crossover cascade, N. Radhoff, A. Studer, Nat. Commun. 2022, 13, 3083. [doi:10.1038/s41467-022-30817-3] Alternating Terpolymers through Cyclopolymerization and Subsequent Orthogonal Functionalization,P. Gerdt, A. Studer, Angew. Chem. Int. Ed. 2022, 61, e202206964. [doi:10.1002/anie.202206964]; Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans, X. Yu, Q.-Y. Meng, C. G. Daniliuc, A. Studer, J. Am. Chem. Soc. 2022, 144, 7072-7079. [doi:10.1021/jacs.2c01735] Oxindole Synthesis via Polar Radical Crossover of Ketene derived Amide Enolates in a Formal [3+2] Cycloaddition, N. Radhoff, A. Studer, Chem. Sci. 2022, 13, 3875-3879. [doi:10.1039/D1SC07134C] Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades, K. Jana, A. Studer, Org. Lett. 2022, 24, 1100-1104. [doi:10.1021/acs.orglett.2c00039] 1,3-Oxyalkynylation of Aryl Cyclopropanes with Ethylnylbenziodoxolones Using Photoredox Catalysis, Z. Zuo, A. Studer, Org. Lett. 2022, 24, 949-954. [doi:10.1021/acs.orglett.1c04319] Radical 1-Fluorosulfonyl-2-alkynylation of Unactivated Alkenes, N. L. Frye, C. G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 2022, 61, e202115593. [doi:10.1002/anie.202115593]; 2,3-Difunctionalized Indoles via Radical Acylation or Trifluoromethylation of ortho-Alkynylphenyl Isonitriles, D. Leifert, F. Weidlich, F. Adler, C. G. Daniliuc, F. A. Adlasmary, A. Studer, Org. Lett. 2022, 24, 284-288. [doi:10.1021/acs.orglett.1c03916] Three-Component 1,2-Carboamination of Vinyl Boronic Esters via Amidyl Radical Induced 1,2-Migration, C. You, A. Studer, Chem. Sci. 2021, 12, 15765-15769. [doi:10.1039/D1SC05811H ] Conformational evolution following the sequential molecular dehydrogenation of PMDI on a Cu(111) surface, L. Liu, A. Timmer, E.Kolodzeiski, H.-Y. Gao, H. Mönig, H. Klaasen, X. Meng, J. Ren, A. Studer, S. Amirjalayer, H. Fuchs, Nanoscale Adv. 2021, 3, 6373-6378. [doi:10.1039/D1NA00590A] Remote Radical Desaturation of Unactivated C−H Bonds in Amides, Y. Xia, K. Jana, A. Studer, Chem. Eur. J. 2021, 27, 16621-16625. [doi:10.1002/chem.202103509] Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes, Z. Zuo, C. G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 2021, 60, 25252-25257. [doi:10.1002/anie.202110304] Transition-Metal-Free Intramolecular Radical Aminoboration of Unactivated Alkenes, D. Zheng, K. Jana, F. A. Alasmary, C. G. Daniliuc, A. Studer, Org. Lett. 2021, 23, 7688-7692. [doi:10.1021/acs.orglett.1c03024] Visible-light Mediated Tryptophan Modification in Oligopeptides Employing Acylsilanes, J. Reimler, A. Studer, Chem. Eur. J. 2021, 27, 15392-15395. [doi:10.1002/chem.202102749] Direct Access to α-Aminosilanes Enabled by Visible-Light-Mediated Multicomponent Radical Cross-Coupling, X. Yu, C. G. Daniliuc, F. A. Alasmary, A. Studer, Angew. Chem. Int. Ed. 2021, 60, 23335-23341. [doi:10.1002/anie.202109252] Regio- and Stereoselective 1,2-Carboboration of Ynamides with Aryldichloroboranes, C. You, M. Sakai, C. G. Daniliuc, K. Bergander, S. Yamaguchi, A. Studer, Angew. Chem. Int. Ed. 2021, 60, 21697-21701. [doi:10.1002/anie.202107647] Intramolecular Hydrogen Atom Transfer Induced 1,2-Migration of Boronate Complexes, D. Wang, K. Jana, A. Studer, Org. Lett. 2021, 23, accepted. [doi:10.1021/acs.orglett.1c01998] Radical Aryl Migration from Boron to Carbon, D. Wang, C. Mück-Lichtenfeld, C. G. Daniliuc, A. Studer, J. Am. Chem. Soc. 2021, 143, 9320-9326. [doi:10.1021/jacs.1c04217] Photo Click Reaction of Acylsilanes with Indoles, C. Stuckhardt, M. Wissing, A. Studer, Angew. Chem. Int. Ed. 2021, 60, accepted. [doi:10.1002/anie.202101689] Remote Site-selective Radical C(sp3)-H Monodeuteration of Amides using D2O, L. Wang, Y. Xia, V. Derdau, A. Studer, Angew. Chem. Int. Ed. 2021, 60, accepted. [doi:10.1002/anie.202104254] Synthesis of Stannylated Aryl Imines and Amines via Aryne Insertion Reactions into Sn−N Bonds, E. Kran, C. Mück-Lichtenfeld, C. G. Daniliuc, A. Studer, Chem. Eur. J. 2021, 27, 9281-9285. [doi:10.1002/chem.202101124] Recent advances in radical chemistry proceeding through pro-aromatic radicals, A. Bhunia, A. Studer, Chem 2021, 7, accepted. [doi:10.1016/j.chempr.2021.03.023] Three-Component Aminoarylation of Electron-Rich Alkenes by Merging Photoredox with Nickel Catalysis, h. Jiang, X. Yu, C. G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 2021, 60, 14399-14404. [doi:10.1002/anie.202101775] Benzylic C−H acylation by cooperative NHC and photoredox catalysis, Q.-Y. Meng, L. Lezius, A. Studer, Nat. Commun. 2021, 12, 2068. [doi:10.1038/s41467-021-22292-z]; highlighted in Synform 2021, 08, A136. Polymerization of silanes through dehydrogenative Si–Si bond formation on metal surfaces, L. Liu, H. Klaasen, M. C. Witteler, B. Schulze Lammers, A. Timmer, H. Kong, H. Mönig, H.-Y. Gao, J. Neugebauer, H. Fuchs, A. Studer, Nat. Chem. 2021, 13, 350-357. [doi:10.1038/s41557-021-00651-z] Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis, K. Liu, A. Studer, J. Am. Chem. Soc. 2021, 143, 4903-4909. [doi:10.1021/jacs.1c01022] Synthesis of Polymers Bearing a Chiral Backbone via Stereospecific Ionic Ring-Opening Polymerization of Chiral Donor-Acceptor Cyclopropanes, A. Emmerich, C. G. Daniliuc, A. Studer, Macromol. Rapid. Commun. 2021, 42, 2100030. [doi:10.1002/marc.202100030] Photo-mediated Intermolecular Coupling of Alkenes with Ketones via Acyloxy Nitroso Compounds, D. Zheng, S. Plöger, C. G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 2021, 60, 8547-8551. [doi:10.1002/anie.202016955] Preparation of α-Perfluoroalkyl Ketones from α,β-unsaturated Ketones via formal Hydroperfluoroalkylation, K. Jana, I. Mizota, A. Studer, Org. Lett. 2021, 23, 1280-1284. [doi:10.1021/acs.orglett.0c04260] Fe-catalyzed anaerobic Mukaiyama-type hydration of alkenes using nitroarenes, A. Bhunia, K. Bergander, C. G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 2021, 60, 8313-8320. [doi:10.1002/anie.202015740]; highlighted in Synfacts 2021, 17(04), 0419. Electronic effects in profluorescent benzotriazinyl radicals: A combined experimental and theoretical study, J. Exner, I. Maisuls, A. Massolle, S. Klabunde, M. R. Hansen, C. A. Strassert, J. Neugebauer, H. Eckert, A. Studer, Phys. Chem. Chem. Phys. 2021, 23, 2999-3007. [doi:10.1039/D0CP05732K] Functionalization of α‐C(sp3)‒H Bonds in Amides Using Radical Translocating Arylating Groups, N. Radhoff, A. Studer, Angew. Chem. Int Ed. 2021, 60, 3561-3565. [doi:10.1002/anie.202013275];highlighted in Synfacts 2021, 17(03), 0295. Azo bond formation on metal surfaces, X. Meng, H. Klaasen, L. Viergutz, B. Schulze Lammers, M. C. Witteler, H. Mönig, S. Amirjalayer, L. Liu, J. Neugebauer, H.-Y. Gao, A. Studer, H. Fuchs, Angew. Chem. Int. Ed. 2021, 60, 1458-1464. [doi:10.1002/anie.202011858] Arynes as Radical Acceptors: TEMPO‐mediated Cascades Comprising Addition, Cyclization and Trapping, M. Scherübl, C. G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 2021, 60, 711-715. [doi:10.1002/anie.202012654] 1,1,2-Trifunctionalization of Terminal Alkynes by Radical Addition-Translocation-Cyclization-Trapping for the Construction of Highly Substituted Cyclopentanes, Y. Yang, C. G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 2021, 60, 2145-2148. [doi:10.1002/anie.202011785] Oligosilanes as Silyl Radical Precursors through Oxidative Si−Si Bond Cleavage using Redox Catalysis, X. Yu, M. Lübbesmeyer, A. Studer, Angew. Chem. Int. Ed. 2021, 60, 675-679. [doi:10.1002/anie.202011738]