Szostak, Michal - Rutgers University - Departments of Chemistry

个人简介

Ph.D., University of Kansas (2009) with Jeffrey Aubé Postdoctoral, Princeton University (2010) with David MacMillan Postdoctoral, University of Manchester (2011-2014) with David Procter

研究领域

The central theme of our research is synthetic organic and organometallic chemistry with a focus on the development of new synthetic methods based on transition metal catalysis and various aspects of transition metal mediated free radical chemistry and their application to the synthesis of biologically active molecules.

近期论文

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Zhou, T.; Gao, P.; Lalancette, R.; Szostak, R.; Szostak, M. “Gold-Catalysed Amine Synthesis by Reductive Hydroamination of Alkynes with Nitroarenes,” Nature Chem. 2024, 16, doi: 10.1038/s41557-024-01624-8. Utecht-Jarzyńska, G.; Shi, S.; Gao, P.; Jarzyński, S.; Rahman, M.; Lalancette, R.; Szostak, R.; Szostak, M. “IPr*F – Highly Hindered, Fluorinated N-Heterocyclic Carbenes,” Chem. Eur. J. 2024, 30, e202402847. Utecht-Jarzyńska, G.; Jarzyński, S.; Rahman, M.; Meng, G.; Lalancette, R.; Szostak, R.; Szostak, M. “IPr# Complexes – Highly-Hindered, Sterically-Bulky Cu(I) and Ag(I) N-Heterocyclic Carbenes: Synthesis, Characterization, and Reactivity,” Organometallics 2024, 43, doi: 10.1021/acs.organomet.4c00333. Liang, Y.; Ma, Y.; Zhou, W.; Cui, Y.; Szostak, M.; Liu, C. “Samarium Diiodide/Samarium-Mediated Direct Deoxygenative Hydroborylation of Ketones with Hydroborane Esters,” Org. Biomol. Chem. 2024, 22, doi: 10.1039/D4OB01287A. Podchorodecka, P.; Dziuk, B.; Junga, R.; Szostak, R.; Szostak, M.; Bisz, E. “IPr*Thia – Wingtip-Flexible, Sterically Hindered, Modular, N,C/S,C-Chelating Thiazole-Donor N-Heterocyclic Carbene Ligands,” Dalton Trans. 2023, 52, doi: 10.1039/D4DT01468E. Tomasini, M.; Voccia, M.; Caporaso, L.; Szostak, M.; Poater, A. “Tuning the Steric Hindrance of Alkylamines: A Predictive Model of Steric Editing of Planar Amines,” Chem. Sci. 2024, 15, 13405-13414. Chen, L.l Zhou, W.; Zhang, J.; Ding, Y.; Szostak, M.; Liu, C. “Deoxygenative Alkynylation of Amides via C=O Bond Cleavage,” Chem. Commun. 2024, 60, 8454-8457. Zhu, Y.; Yang, S.; Zhou, T.; Szostak, M. “[(NHC)Pd(OAc)2]: Highly Active Carboxylate Pd(II)–NHC (NHC = N-Heterocyclic Carbene) Precatalysts for Suzuki–Miyaura and Buchwald–Hartwig Cross-Coupling of Amides by N–C(O) Activation,” J. Org. Chem. 2024, 89, doi: 10.1021/acs.joc.4c00103. (Special issue: Next-Generation Cross- Coupling Chemistry). Zhou, T.; Utecht-Jarzyńska, G.; Szostak, M. “Ring-Expanded N-Heterocyclic Carbene (reNHC) Complexes: Applications in Transition Metal Catalysis,” Coord. Chem. Rev. 2024, 512, 215867. Gao, Y.; Hu, Y.; Ye, J.; Ma, Z.; Feng, J.; Liu, X.; Lei, P.; Szostak, M. “Pd–NHC (NHC = N-Heterocyclic Carbene)-Catalyzed B-Alkyl Suzuki Cross-Coupling of 2-Pyridyl Ammonium Salts by N–C Activation: Application to the Discovery of Agrochemical Molecular Hybrids,” Org. Lett. 2024, 26, 2309-2314. Zhang, J.; Liu, T.; Zhang, G.; Cai, J.; Wang, Y.; Tong, J.; Ma, Y.; Szostak, R.; Szostak, M. “Indazolin-3-ylidenes (Indy*): Easily Accessible, Sterically-Hindered Indazole-Derived N-Heterocyclic Carbenes and Their Application in Gold Catalysis,” Dalton Trans. 2024, 53, 4260-4265. Chen, L.; Ji, H.; Ding, Y.; Szostak, M.; Liu, C. “Palladium-Catalyzed Decarbonylative Sonogashira Alkynylation of Carboxylic–Phosphoric Anhydrides,” J. Org. Chem. 2024, 89, 2665-2674. Szostak, M.; Bera, S. “Sterically Hindered 1H-1,2,3-triazol-5-ylidene Abnormal N-Heterocyclic Carbene (aNHC) Ligands, Catalyst Complexes Thereof, and Methods Using Same,” U.S. 63/621,472, Jan 16, 2024. Zhao, Q.; Rahman, M.; Zhou, T.; Yang, S.; Lalancette, R.; Szostak, R.; Szostak, M. “Wingtip-Flexible N-Heterocyclic Carbenes: Unsymmetrical Connection between IMes and IPr,” Angew. Chem. Int. Ed. 2024, 63, e202318703. Zhang, W.; Ma, J.; Zhou, F.; Szostak, M.; Liu, C. “Carboxylic Acids as Double Aryl Group Donors for Biaryl Synthesis,” Org. Chem. Front. 2023, 10, 5698-5704. Podchorodecka, P.; Dziuk, B.; Szostak, R.; Szostak, M.; Bisz, E. “IPr*Oxa – A New Class of Sterically-Hindered, Wingtip-Flexible N,C-Chelating Oxazole-Donor N-Heterocyclic Carbene Ligands,” Dalton Trans. 2023, 52, 13608-13617. Zhu, X.; Wan, K.; Zhang, J.; Zhao, H.; He, Y.; Ma, Y.; Yang, X.; Szostak, M. “Esterification of Thioamides via Selective N–C(S) Cleavage under Mild Conditions,” Org. Lett. 2023, 25, 6149-6154. Rahman, M.; Zhao, Q.; Meng, G.; Lalancette, R.; Szostak, R.; Szostak, M. “[IPr#–PEPPSI]: A Well-Defined, Highly Hindered and Broadly Applicable Pd(II)–NHC (NHC = N-Heterocyclic Carbene) Precatalyst for Cross-Coupling Reactions,” Molecules 2023, 28, 5833. (Featured Papers in Organometallic Chemistry; open access: https://doi.org/10.3390/molecules28155833) Rahman, M.; Gao, P.; Zhao, Q.; Lalancette, R.; Szostak, R.; Szostak, M. “[Au(Np#)Cl]: Highly Reactive and Broadly Applicable Au(I)–NHC Catalysts for Alkyne π-Activation Reactions,” Catl. Sci. Technol. 2023, 13, 5131-5139. Ji, H.; Cao, H.; Wang, G.; Xing, F.; Szostak, M.; Liu, C. “Predominant Intermolecular Decarbonylative Thioetherification of Carboxylic Acids Using Nickel Precatalysts,” Org. Chem. Front. 2023, 10, 4275-4281. Yang, S.; Yu, X.; Liu, Y.; Tomasini, M.; Caporaso, L.; Poater, A.; Cavallo, L.; Cazin, C.; Nolan, S.; Szostak, M. “Suzuki–Miyaura Cross-Coupling of Amides by N–C Cleavage Mediated by Air-Stable, Well-Defined [Pd(NHC)(sulfide)Cl2] Catalysts: Reaction Development, Scope and Mechanism,” J. Org. Chem. 2023, 88, 10858-10868. Rahman, M. M.; Meng, G.; Bisz, E.; Dziuk, B.; Lalancette, R.; Szostak, R.; Szostak, M. “ItOct (ItOctyl) – Pushing the Limits of ItBu: Highly Hindered Electron-Rich N-Aliphatic N-Heterocyclic Carbenes,” Chem. Sci. 2023, 14, 5141-5147. (Check out a Highlight in Chemistry World, NHC Ligands Bulk Up by Laura Smith) Hu, Y.; Gao, Y.; Ye, J.; Ma, Z.; Feng, J.; Liu, X.; Lei, P.; Szostak, M. “Suzuki–Miyaura Cross-Coupling of 2-Pyridyl Trimethylammonium Salts by N–C Activation Catalyzed by Air- and Moisture-Stable Pd–NHC Precatalysts: Application to the Discovery of Agrochemicals,” Org. Lett. 2023, 25, 2975-2980. Liu, X.; Li, X.; Liu, L.; Huang, T.; Chen, W.; Szostak, M.; Chen. T. “Pd/Cu-Catalyzed Synthesis of Internal and Sila-Ynones by Direct Selective Acyl Sonogashira Cross-Coupling of Carboxylic Acids with Terminal Alkynes,” ACS Catal. 2023, 13, 5819-5827. Bie, F.; Liu, X.; Szostak, M.; Liu, C. “Decarbonylative Alkynylation of Aryl Anhydrides via Palladium Catalysis,” J. Org. Chem. 2023, 88, 4442-4451. Gao, P.; Szostak, M. “Hydration Reactions Catalyzed by Transition Metal–NHC (NHC = N-Heterocyclic Carbene) Complexes,” Coord. Chem. Rev. 2023, 485, 215110. Nan, J.; Ren, X.; Yan, Q.; Liu, S.; Wang, J.; Ma, Y.; Szostak, M. “Hypervalent Iodine-Promoted Twofold Oxidative Coupling of Amines with Amides and Thioamides: Chemoselective Pathway to Oxazoles and Thiazoles,” Chem. Sci. 2023, 14, 3338-3345. Liu, C.; Szostak, M. “Amide N–C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling,” SynOpen 2023, 7, 88-101. (Open access: https://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-2035-6733.pdf) Liu, C.; Xing, Y. Y.; Zhou, T.; Chen, T.; Hong, X.; Szostak, M. “Carboxylic-Phosphoric Anhydrides as Direct Electrophiles for Decarbonylative Hirao Cross-Coupling of Carboxylic Acids: DFT Investigation of Mechanistic Pathway,” Chem. Asian J. 2023, 18, e202201262. (Special issue: Celebration of Professor Kendall N. Houk 80th birthday) Liu, F.; Anand, L.; Szostak, M. “Diversification of Indoles and Pyrroles by Molecular Editing: New Frontiers in Heterocycle-to-Heterocycle Transmutation,” Chem. Eur. J. 2023, 29, e202300096. Zhang, J.; Wang, X.; Liu, J.; Wang, X.; Yang, X.; Zhao, Q.; Ma, Y.; Fang, R.; Szostak, M. “Ruthenium(0)-Catalyzed Cross-Coupling of Aryl Methyl Ethers with Organoboranes by Selective C–O cleavage,” Org. Chem. Front. 2023, 10, 1423-1428. Gao, P.; Xu, J.; Zhou, T.; Liu, Y.; Bisz, E.; Dziuk, B.; Lalancette, R.; Szostak, R.; Zhang, D.; Szostak, M. “Activation of Aryl Halides at Gold(I) by N-Heterocyclic Carbenes: L-Shaped Heterobidentate ImPy (Imidazo[1,5-a]pyridin-ylidene) N,C Ligands for Oxidant-Free Au(I)/Au(III) Catalysis,” Angew. Chem. Int. Ed. 2023, 62, e202218427. Yang, S.; Yu, X.; Szostak, M. “Divergent Acyl and Decarbonylative Liebeskind−Srogl Cross-Coupling of Thioesters by Cu-Cofactor and Pd–NHC (NHC = N-Heterocyclic Carbene) Catalysis,” ACS Catal. 2023, 13, doi: 10.1021/acscatal.2c05550. Yang, S.; Zhou, T.; Yu, X.; Szostak, M. “Ag–NHC Complexes in the π-Activation of Alkynes,” Molecules 2023, 28, 950. (Special Issue: Featured Reviews in Organometallic Chemistry; open access: https://doi.org/10.3390/molecules28030950) Bisz, E.; Podchorodecka, P.; Li, H.; Ochedzan-Siodlak, W.; Jie, A.; Szostak, M. “Sequential Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Chlorobenzamides/Chemoselective Amide Reduction and Reductive Deuteration to Benzylic Alcohols,” Molecules 2023, 28, 223. (Special Issue: Metal-Induced Molecule Activation and Coupling Reactions; open access: https://doi.org/10.3390/molecules28010223) Liu, S.; Liang, J.; Zhang, P.; Li, Z.; Jiao, L. Y.; Jia, W.; Ma, Y. Szostak, M. “Ruthenium-Catalyzed Divergent Deaminative and Denitrative C–N Cleavages: Facile Access to Quinoxalines,” Org. Chem. Front. 2023, 10, 22-29. Gao, P.; Rahman, P.; Zamalloa, A.; Feliciano, J.; Szostak, M. “Classes of Amides that Undergo Selective N–C Amide Bond Activation: The Emergence of Ground-State Destabilization,” J. Org. Chem. 2023, 88, DOI: 10.1021/acs.joc.2c01094. (Featured as the Front Cover). Yang. S.; Yu, X.; Poater, A.; Cavallo, L.; Cazin, C. S. J.; Nolan, S. P.; Szostak, M. “Buchwald–Hartwig Amination and C–S/S–H Metathesis of Aryl Sulfides by Selective C–S Cleavage Mediated by Air- and Moisture-Stable [Pd(NHC)(μ-Cl)Cl]2 Precatalysts: Unified Mechanism for Activation of Inert C–S Bonds,” Org. Lett. 2022, 24, 9210-9215. Kardela, M.; Halikowska-Tarasek, K.; Szostak, M.; Bisz, E. “Enhanced Activity of Bulky N-Heterocylic Carbenes in Nickel–NHC Catalyzed Kumada–Corriu Cross-Coupling of Aryl Tosylates,” Catl. Sci. Technol. 2022, 12, 7275-7280. Zhang, J.; Li, X.; Li, T.; Zhang, G.; Wan, K.; Ma, Y.; Fang. R.; Szostak, R.; Szostak, M. “Copper(I)–Thiazol-2-ylidenes: Highly Reactive N-Heterocyclic Carbenes for the Hydroboration of Terminal and Internal Alkynes. Ligand Development, Synthetic Utility, and Mechanistic Studies,” ACS Catal. 2022, 12, 15323-15333. Chu, W.; Zhou, T.; Bisz, E.; Dziuk, B.; Lalancette, R.; Szostak, R.; Szostak, M. “CAAC–IPr*: Easily Accessible, Highly Sterically-Hindered Cyclic (Alkyl)(Amino)Carbenes,” Chem. Commun. 2022, 58, 13467-13470. Zhang, J.; Liu, J.; Wang, X.; Yang, X.; Ma, Y.; Fang, R.; Zhao, Q.; Szostak, M. “Ruthenium-Catalyzed C–F Bond Arylation of Polyfluoroarenes: Polyfluorinated Biaryls by Integrated C–F/C–H Functionalization,” ACS Catal. 2022, 12, 14337-14346. Yang, S.; Li, H.; Yu, X.; An, J.; Szostak, M. “Suzuki–Miyaura Cross-Coupling of Aryl Fluorosulfonates Mediated by Air- and Moisture-stable [Pd(NHC)(μ-Cl)Cl]2 Precatalysts: Broad Platform for C–O Cross-Coupling of Stable Phenolic Electrophiles,” J. Org. Chem. 2022, 87, 15250-15260. Zhou, T.; Gao, P.; Bisz, E.; Dziuk, B.; Lalancette, R.; Szostak, R.; Szostak, M. “Well-Defined, Air- and Moisture-Stable Palladium–Imidazo[1,5-a]pyridin-3-ylidene Complexes: A Versatile Catalyst Platform for Cross-Coupling Reactions by L-Shaped NHC Ligands,” Catl. Sci. Technol. 2022, 12, 6581-6589. Lei, P.; Wang, Y.; Zhang, C.; Hu, Y.; Feng, J.; Ma, Z.; Liu, X.; Szostak, R.; Szostak, M. “Sonogashira Cross-Coupling of Aryl Ammonium Salts by Selective C–N Activation Catalyzed by Air- and Moisture-Stable, Highly Active [Pd(NHC)(3-CF3-An)Cl2] (An = Aniline) Precatalysts,” Org. Lett. 2022, 24, 6310-6315. Rahman, M.; Zhao, Q.; Meng, G.; Szostak, R.; Szostak, M. “[Ni(Np#)(η5-Cp)Cl]: Flexible, Sterically Bulky, Well-Defined, Highly Reactive Complex for Nickel-Catalyzed Cross-Coupling,” Organometallics 2022, 41, 2597-2604. Tomasini, M.; Zhang, J.; Zhao, H.; Besalu, E.; Falivene, L.; Caporaso, L.; Szostak, M.; Poater, A. “A Predictive Journey Towards Trans-Thioamides/Amides,” Chem. Commun. 2022, 58, 9950-9953. Rahman, M.; Zhang, J.; Zhao, Q.; Feliciano, J.; Bisz, E.; Dziuk, B.; Lalancette, R.; Szostak, R.; Szostak, M. “Pd−PEPPSI N-Heterocyclic Carbene Complexes from Caffeine: Application in Suzuki, Heck, and Sonogashira Reactions,” Organometallics 2022, 41, 2281-2290. Zhao, Q.; Li, G.; Nareddy, P.; Jordan, F.; Lalancette, R.; Szostak, R.; Szostak, M. “Structures of the Most Twisted Thioamide and Selenoamide: Effect of Higher Chalcogens of Twisted Amides on N−C(X) Resonance,” Angew. Chem. Int. Ed. 2022, 61, e202207346. Zhang, J.; Li, T.; Li, X.; Zhang, G.; Fang, S.; Yan, W.; Li, X.; Yang, X.; Ma, Y.; Szostak, M. “An Air-Stable, Well-Defined Palladium–BIAN–NHC Chloro Dimer: A Fast-Activating, Highly Efficient Catalyst For Cross-Coupling,” Chem. Commun. 2022, 58, 7404-7407. Zhang, J.; Li, T.; Li, X.; Lv, A.; Li, X.; Wang, Z.; Wang, R.; Ma, Y.; Fang, R.; Szostak, R.; Szostak, M. “Thiazol-2-ylidenes as N-Heterocyclic Carbene Ligands with Enhanced Electrophilicity for Transition Metal Catalysis,” Comm. Chem. 2022, 5, no. 60, DOI: 10.1038/s42004-022-00675-7. (Open Access) Zhang, J.; Wang, Y.; Zhang, Y.; Liu, T.; Fang, S.; Wang, R.; Ma, Y.; Fang, R.; Szostak, R.; Szostak, M. “Application of Indazolin-3-ylidenes in Catalysis: Steric Tuning of Nonclassical Formally Normal N-Heterocyclic Carbenes with Dual Electronic Character for Catalysis,” Organometallics 2022, 41, 1115–1124. (Featured as the Front Cover). Zhang, J.; Li, T.; Wang, X.; Ma, Y.; Szostak, M. “Modern Homologation Reactions of Sulfoxonium Ylides via C–H Activation,” Chapter 9, In Homologation Reactions, Pace, V. Ed. Wiley, 2022. Gao, P.; Meng, G.; Hammadi, B.; Szostak, M. “C–H Functionalization Using Carboxylic Acids and Carboxylic Acid Derivatives as Electrophiles under Redox-Neutral Conditions,” Vol. 14, Chapter 180, In Handbook of C–H Functionalization, Maiti, D. Ed. Wiley, 2022. Zhang, J.; Zhao, H.; Li, G.; Zhu, X.; Shang, L.; He, Y.; Liu, X.; Ma, Y.; Szostak, M. “Transamidation of Thioamides with Nucleophilic Amines: Thioamide N–C(S) Activation by Ground-State-Destabilization,” Org. Biomol. Chem. 2022, 20, 5981-5988. (Special Issue: New Talent) Zuo, D.; Wang, Q.; Liu, L.; Huang, T.; Szostak, M.; Chen, T. “Highly Chemoselective Transamidation of Unactivated Tertiary Amides by Electrophilic N–C(O) Activation via Amide-to-Acyl Iodide Re-Routing,” Angew. Chem. Int. Ed. 2022, 61, e202202794. (Top Most Accessed Article in April 2022) Zhang, J.; Rahman, M.; Zhao, Q.; Feliciano, J.; Bisz, E.; Dziuk, B.; Lalancette, R.; Szostak, R.; Szostak, M. “N–Heterocyclic Carbene Complexes of Nickel(II) from Caffeine and Theophylline: Sustainable Alternative to Imidazol-2-ylidenes,” Organometallics 2022, 41, 1806-1815. (Special Issue: Sustainable Chemistry) Zhang, J.; Zhang, P.; Ma, Y.; Szostak, M. “Mechanochemical Synthesis of Ketones via Chemoselective Suzuki–Miyaura Cross-Coupling of Acyl Chlorides,” Org. Lett. 2022, 24, 2338-2343. Szostak, M.; Zhou, T.; Shiyi, Y. “Substituted N-Heterocyclic Carbene (NHC) Ligands, Catalyst Complexes Thereof, and Methods Using Same,” U.S. 63/318,481, Mar 10, 2022. Szostak, M.; Gao, P. “Heterobidentate N-Heterocyclic Carbene (NHC) Ligands, Catalyst Complexes Thereof, and Methods Using Same,” U.S. 63/292,235, Dec 21, 2021. Cervantes-Reyes, A.; Smith, A. C.; Chinigo, G. M.; Blakemore, D. C.; Szostak, M. “Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls,” Org. Lett. 2022, 24, 1678-1683. Bera, S. S.; Szostak, M. “Cobalt–N-Heterocyclic Carbene Complexes in Catalysis,” ACS Catal. 2022, 12, 3111-3137. Li, G.; Xing, Y.; Zhao, H.; Zhang, J.; Hong, X.; Szostak, M. “Chemoselective Transamidation of Thioamides by Transition-Metal-Free N–C(S) Transacylation,” Angew. Chem. Int. Ed. 2022, 61, e202200144. Wang, C. A.; Rahman, M.; Bisz, E.; Dziuk, B.; R; Szostak, R.; Szostak, M. “Palladium-NHC (NHC = N–heterocyclic Carbene)-Catalyzed Suzuki–Miyaura Cross-Coupling of Alkyl Amides,” ACS Catal. 2022, 12, 2426-2433. Zhang, Y.; Szostak, M. “Synthesis of Natural Products by C–H Functionalization of Heterocycles,” Chem. Eur. J. 2022, 28, e202104278. Zhang, J.; Zhang, P.; Shao, L.; Wang, R.; Ma, Y.; Szostak, M. “Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N–C Cleavage,” Angew. Chem. Int. Ed. 2022, 61, DOI: 10.1002/anie.202114146. Liu, C.; Szostak, M. “Decarbonylative Sonogashira Cross-Coupling: Fruitful Marriage of Alkynes with Carboxylic Acid Electrophiles,” Org. Chem. Front. 2022, 9, DOI: 10.1039/D1QO01539G. Li, D. H.; Lan, X. B.; Song, A. X.; Rahman, M.; Xu, C.; Huang, F. D.; Szostak, R.; Szostak, M.; Liu, F. S. “Buchwald-Hartwig Amination of Coordinating Heterocycles Enabled by Large-but-Flexible Pd–BIAN–NHC Catalysts,” Chem. Eur. J. 2022, 28, DOI: 10.1002/chem.202103341.