Chirik, Paul - Princeton University - Department of Chemistry

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Princeton University Department of Chemistry
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个人简介

Ph.D. California Institute of Technology, June 2000 Advisor: John E. Bercaw Thesis: Ancillary Ligand Effects on Fundamental Transformations in Metallocene Catalyzed Olefin Polymerization. B.S. Virginia Tech, Magna Cum Laude, In Honors, May 1995 Advisor: Joseph S. Merola Thesis: Studies in to Iridium- and Rhodium- Hydrogenation Catalysts for Alkene Hydrogenation in Aqueous Solution. Experience Edwards S. Sanford Professor, Princeton University 2011 – present Peter J. W. DeBye Professor, Cornell University 2009 – 2011 Associate Professor, Cornell University 2006 – 2009 Assistant Professor, Cornell University 2001 – 2006 Postdoctoral Fellow, Massachusetts Institute of Technology 2000 – 2001 Selected Honors and Awards Gabor Somorjai Award for Creative Research in Catalysis 2021 Catalysis Society of South Africa (CATSA) Eminent Visitor 2021 Linus Pauling Medal (postponed to 2021) 2020 Rylander Award in Catalysis Sponsored by BASF (postponed) 2020 Eni Award, Advanced Environmental Solutions Prize 2019 ACS Catalysis Lectureship for Advancement of Catalysis Science 2017 Presidential Green Chemistry Challenge Award 2016 Arthur C. Cope Scholar Award, American Chemical Society 2009 Bessel Fellow of the Alexander von Humboldt Foundation 2008 Camille Dreyfus-Teacher Scholar 2006 Stephen and Margery Russell Distinguished Teaching Award 2005 David and Lucile Packard Fellow in Science and Engineering 2004 NSF CAREER Award 2003 Herbert Newby McCoy Award for Outstanding Dissertation, Caltech 2000

研究领域

Cobalt- and Iron-Catalyzed Asymmetric Alkene Hydrogenation Asymmetric alkene hydrogenation is responsible for more than 50% of the chiral material in the pharmaceutical industry. State-of-the-art catalysts rely on precious metals such as rhodium, ruthenium and iridium. Our team has pioneered the application of more earth-abundant metals such as iron and cobalt for these transformations. With cobalt, catalysts that are more active and enantioselective compared to precious metals have been discovered. More recent efforts have focused on catalysts differentiated by a single-electron to enable distinct reactivity – most notable in the asymmetric synthesis of sitagliptin. Continuing efforts are focused on the development of new metal precursors to facilitate catalyst discovery by high throughput experimentation and expanding the scope of asymmetric transformations that are currently beyond the reach of precious metals. Iron Catalysis for a Sustainable Hydrocarbon Future Hydrocarbons are an indispensable component of modern life with applications ranging from fuels to plastics. Iron catalysts, supported by redox-active ligands, enable new transformations from the fundamental building blocks of the chemical industry. Specifically, we have developed selective iron-catalyzed [2+2] and [4+4] cycloaddition reactions of feedstock alkenes and dienes, providing pathways to upgrade bioderived hydrocarbons. In the case of cyclobutane products, the reactions are reversible opening a gateway to chemically recyclable polyolefins. Efforts are devoted to expanding the scope of iron catalysts capable of such cycloaddition transformations and to synthesize new hydrocarbon architectures towards accessing sustainable aviation fuels and chemically recyclable plastics. Iron and Cobalt Catalysts for Cross Coupling Transition-metal catalyzed cross-coupling is a transformative method for C–C bond formation that accounts for 12% of reactions conducted in the pharmaceutical industry. Next-generation cross-coupling catalysts are needed to support the greater three-dimensionality of pharmaceuticals and to reliance on precious metals in the discovery and manufacture of medicines. The Chirik group is developing catalysts based on cobalt and iron for C(sp2)-C(sp3) Suzuki coupling that rely on abundant neutral boron reagents and alkyl halide electrophiles. The mechanisms of these reactions are also investigated and involve high spin metal complexes in weak ligand fields. This intersection of state-of-the-art physical inorganic chemistry, catalysis and organic methodology drives future catalyst development. Iron and Cobalt Catalysts for Electronically-Driven, Site-Selective C–H Functionalization Metal-catalyzed C–H functionalization has emerged as an intense area of study due to its transformative impact on chemical synthesis. Catalysts for these transformations typically rely on precious metals such as palladium and iridium. The Chirik group has developed a series of C–H functionalization reactions using Earth-abundant 3d transition metal catalysts, including ortho-and meta-C–H borylation of fluoroarenes using pincer-ligated cobalt(I) complexes, and directed-ortho C–H alkylation by cationic bis(phosphine)cobalt(III) metallacycles. Ongoing efforts are towards iron-catalyzed C–H borylation and expanding the scope of C–C bond forming reactions.

近期论文

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A butadiene-derived semicrystalline polyolefin with two-tiered chemical recyclability. Cherish Nie, Shawn M. Maguire, Callie W. Zheng, Megan Mohadjer Beromi, Richard A. Register, Rodney D. Priestley, Emily C. Davidson, Paul J. Chirik Chem 2023, 10, 1–15 Kinetic and thermodynamic control of C(sp2)–H activation enables site-selective borylation. Jose B. Roque, Alex M. Shimozono, Tyler P. Pabst, Gabriele Hierlmeier, Paul O. Peterson, and Paul J. Chirik Science 2023, 382, 1165-1170 Iridium-Catalyzed Hydrogenation of a Phenoxy Radical to the Phenol: Overcoming Catalyst Deactivation with Visible Light Irradiation. Junho Kim, Yoonsu Park, and Paul J. Chirik Inorg. Chem. 2023, 62, 48, 19582–19592 Phenoxythiazoline (FTz)-Cobalt(II) Precatalysts Enable C(sp2)–C(sp3) Bond-Formation for Key Intermediates in the Synthesis of Toll-like Receptor 7/8 Antagonists. Dr. L. Reginald Mills, Francesca Di Mare, Dr. David Gygi, Dr. Heejun Lee, Dr. Eric M. Simmons, Junho Kim, Dr. Steven R. Wisniewski, Prof. Dr. Paul J. Chirik Angew. Chem. Int. Ed. 2023, e202313848 Quinoline Pyridine(Imine) Iron Complexes as Catalysts for the 1,4-Hydrovinylation of 1,3-Dienes. Coralie Duchemin, Amelia I. Liu, Junho Kim, and Paul J. Chirik Organometallics 2023, 42, 21, 3109–3119 Arene Insertion with Pincer-Supported Molybdenum-Hydrides: Determination of Site Selectivity, Relative Rates, and Arene Complex Formation. Gabriele Hierlmeier, Paolo Tosatti, Kurt Puentener, and Paul J. Chirik J. Am. Chem. Soc. 2023, 145, 38, 21027–21039 Mechanistic Investigations of Phenoxyimine–Cobalt(II)-Catalyzed C(sp2)–C(sp3) Suzuki–Miyaura Cross-Coupling. L. Reginald Mills, David Gygi, Eric M. Simmons, Steven R. Wisniewski, Junho Kim, and Paul J. Chirik J. Am. Chem. Soc. 2023, 145, 31, 17029–17041 CS-Symmetric Pyridine(diimine) Iron Methyl Complexes for Catalytic [2+2] Cycloaddition and Hydrovinylation: Metallacycle Geometry Determines Selectivity. Coralie Duchemin, Junho Kim, and Paul J. Chirik JACS Au 2023, 3, 7, 2007–2024 C(sp3)–C(sp2) Reductive Elimination versus β-Hydride Elimination from Cobalt(III) Intermediates in Catalytic C–H Functionalization. William G. Whitehurst, Junho Kim, Stefan G. Koenig, and Paul J. Chirik ACS Catal. 2023, 13, 13, 8700–8707 Asymmetric Hydrogenation of Indazole-Containing Enamides Relevant to the Synthesis of Zavegepant Using Neutral and Cationic Cobalt Precatalysts. Lauren N. Mendelsohn, Connor S. MacNeil, Madison R. Esposito, Tyler P. Pabst, David K. Leahy, Ian W. Davies, and Paul J. Chirik Org. Lett. 2023, XXXX, XXX, XXX-XXX Exploring the Effect of Pincer Rigidity on Oxidative Addition Reactions with Cobalt(I) Complexes. Boran Lee, Tyler P. Pabst, Gabriele Hierlmeier, and Paul J. Chirik Organometallics 2023, 42, 8, 708–718 Pentamethylcyclopentadienyl Metalloradical Iron Complexes Containing Redox Noninnocent α-Diimine-Type Ligands: Synthesis, Molecular, and Electronic Structures. Yoonsu Park, Hongyu Zhong, Tyler P. Pabst, Junho Kim, and Paul J. Chirik Organometallics 2023, 42, 6, 465–472 Collaboration as a Key to Advance Capabilities for Earth-Abundant Metal Catalysis. Paul J. Chirik, Keary M. Engle, Eric M. Simmons, and Steven R. Wisniewski Org. Process Res. Dev. 2023, 27, 7, 1160–1184 Bimolecular Reductive Elimination of Ethane from Pyridine(diimine) Iron Methyl Complexes: Mechanism, Electronic Structure, and Entry into [2+2] Cycloaddition Catalysis. Carli B. Kovel, Jonathan M. Darmon, S. Chantal E. Stieber, Gisselle Pombar, Tyler P. Pabst, Bastian Theis, Zoë R. Turner, Ökten Üngör, Michael Shatruk, Serena DeBeer, and Paul J. Chirik J. Am. Chem. Soc. 2023, 145, 9, 5061–5073 Iron-Catalyzed C(sp2)–C(sp3) Suzuki–Miyaura Cross-Coupling Using an Alkoxide Base. Paul O. Peterson, Matthew V. Joannou, Eric M. Simmons, Steven R. Wisniewski, Junho Kim, and Paul J. Chirik ACS Catal. 2023, 13, 4, 2443–2448 Identification of Cyclohexadienyl Hydrides as Intermediates in Molybdenum-Catalyzed Arene Hydrogenation. Gabriele Hierlmeier, Paolo Tosatti, Kurt Puentener, Paul James Chirik Angew. Chem. Int. Ed. 2023, 62, e202216026 Catalytic N–H Bond Formation Promoted by a Ruthenium Hydride Complex Bearing a Redox-Active Pyrimidine-Imine Ligand. Sangmin Kim, Junho Kim, Hongyu Zhong, Grace B. Panetti, and Paul J. Chirik J. Am. Chem. Soc. 2022, 144, 45, 20661–20671 Alcohol Synthesis by Cobalt-Catalyzed Visible-Light-Driven Reductive Hydroformylation. Connor S. MacNeil, Lauren N. Mendelsohn, Tyler P. Pabst, Gabriele Hierlmeier, and Paul J. Chirik J. Am. Chem. Soc. 2022, 144, 42, 19219–19224 C–H Activation by Isolable Cationic Bis(phosphine) Cobalt(III) Metallacycles. William G. Whitehurst, Junho Kim, Stefan G. Koenig, and Paul J. Chirik J. Am. Chem. Soc. 2022, 144, 41, 19186–19195 Mechanistic Investigations of the Asymmetric Hydrogenation of Enamides with Neutral Bis(phosphine) Cobalt Precatalysts. Lauren N. Mendelsohn, Ljiljana Pavlovic, Hongyu Zhong, Max R. Friedend, Michael Shevlin, Kathrin H. Hopmann, and Paul J. Chirik J. Am. Chem. Soc. 2022, 144, 34, 15764–15778 Cobalt-Catalyzed Asymmetric Hydrogenation of Enamides: Insights into Mechanisms and Solvent Effects. Ljiljana Pavlovic, Lauren N. Mendelsohn, Hongyu Zhong, Paul J. Chirik, and Kathrin H. Hopmann Organometallics 2022, 41, 1872–1882. Nickel-Catalyzed Dimerization of Di- and Trisubstituted Olefins. Sam Yruegas, Michele Paccagnini, Suzzy C. Ho, Aaron Sattler, and Paul J. Chirik Organometallics 2022, 41, 2059–2066. C(sp2)–H Activation with Bis(silylene)pyridine Cobalt(III) Complexes: Catalytic Hydrogen Isotope Exchange of Sterically Hindered C–H Bonds. Jose B. Roque, Tyler P. Pabst, and Paul J. Chirik ACS Catal. 2022, 12, 8877–8885. Molybdenum-Catalyzed Asymmetric Hydrogenation of Fused Arenes and Heteroarenes. Peter Viereck, Gabriele Hierlmeier, Paolo Tosatti, Tyler P. Pabst, Kurt Puentener, and Paul J. Chirik J. Am. Chem. Soc. 2022, 144, 11203–11214. Cationic Bis(phosphine) Cobalt(I) Arene Complexes as Precatalysts for the Asymmetric Synthesis of Sitagliptin. Connor S. MacNeil, Hongyu Zhong, Tyler P. Pabst, Michael Shevlin, and Paul J. Chirik ACS Catal. 2022, 12, 4680–4687. Development of Cobalt Catalysts for the meta-Selective C(sp2)–H Borylation of Fluorinated Arenes. Tyler P. Pabst and Paul J. Chirik J. Am. Chem. Soc. 2022, 144, 6465–6474. Ammonia synthesis by photocatalytic hydrogenation of a N2-derived molybdenum nitride. Sangmin Kim, Yoonsu Park, Junho Kim, Tyler P. Pabst, and Paul J. Chirik Nature Synthesis 2022, 1, 297–303 Three-Component Coupling of Arenes, Ethylene, and Alkynes Catalyzed by a Cationic Bis(phosphine) Cobalt Complex: Intercepting Metallacyclopentenes for C–H Functionalization. William G. Whitehurst, Junho Kim, Stefan G. Koenig, and Paul J. Chirik J. Am. Chem. Soc. 2022, 144, 4530–4540. (PNP)Cobalt-Catalyzed Olefination of Diazoalkanes. Sam Yruegas, Scott P. Semproni, and Paul J. Chirik Organometallics 2022, ASAP. Visible-Light-Driven, Iridium-Catalyzed Hydrogen Transfer: Mechanistic Studies, Identification of Intermediates, and Catalyst Improvements. Yoonsu Park, Lei Tian, Sangmin Kim, Tyler P. Pabst, Junho Kim, Gregory D. Scholes, and Paul J. Chirik JACS Au 2022, 2, 407–418. Cobalt-Catalyzed C(sp2)–C(sp3) Suzuki-Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands. L. Reginald Mills, David Gygi, Jacob R. Ludwig, Eric M. Simmons, Steven R. Wisniewski, Junho Kim, and Paul J. Chirik ACS Catal. 2022, 12, 1905–1918. Effect of Pincer Methylation on the Selectivity and Activity in (PNP)Cobalt-Catalyzed C(sp2)–H Borylation. Boran Lee, Tyler P. Pabst, and Paul J. Chirik Organometallics 2021, 40, 3766–3774. Well-Defined Cationic Cobalt(I) Precatalyst for Olefin-Alkyne [2+2] Cycloaddition and Olefin-Diene Hydrovinylation Reactions: Experimental Evidence for Metallacycle Intermediates. Marcus E. Farmer, Lauren E. Ehehalt, Tyler P. Pabst, Matthew T. Tudge, and Paul J. Chirik Organometallics 2021, 40, 3599–3607. Catalyst Design Principles Enabling Intermolecular Alkene-Diene [2+2] Cycloaddition and Depolymerization Reactions. Megan Mohadjer Beromi, Jarod M. Younker, Hongyu Zhong, Tyler P. Pabst, and Paul J. Chirik J. Am. Chem. Soc. 2021, 143, 17793–17805. Visible light enables catalytic formation of weak chemical bonds with molecular hydrogen. Yoonsu Park, Sangmin Kim, Lei Tian, Hongyu Zhong, Gregory D. Scholes, and Paul J. Chirik Nat. Chem. 2021, 13, 969–976. Synthesis, Electronic Structure, and Reactivity of a Planar Four-Coordinate, Cobalt–Imido Complex. Yoonsu Park, Scott P. Semproni, Hongyu Zhong, and Paul J. Chirik Angew. Chemie Int. Ed. 2021, 60, 14376–14380. Oxidative Addition of Aryl and Alkyl Halides to a Reduced Iron Pincer Complex. Stephan M. Rummelt, Paul O. Peterson, Hongyu Zhong, and Paul J. Chirik J. Am. Chem. Soc. 2021, 143, 5928–5936. Synthesis and Asymmetric Alkene Hydrogenation Activity of C2-Symmetric Enantioenriched Pyridine Dicarbene Iron Dialkyl Complexes. Peter Viereck, Stephan M. Rummelt, Natalia A. Soja, Tyler P. Pabst, and Paul J. Chirik Organometallics 2021, 40, 1053–1061. A Tutorial on Selectivity Determination in C(sp2)–H Oxidative Addition of Arenes by Transition Metal Complexes. Tyler P. Pabst and Paul J. Chirik Organometallics 2021, 40, 813–831. Iron-catalysed synthesis and chemical recycling of telechelic 1,3-enchained oligocyclobutanes. Megan Mohadjer Beromi, C. Rose Kennedy, Jarod M. Younker, Alex Carpenter, Sarah J. Mattler, Joseph A. Throckmorton, and Paul J. Chirik Nat. Chem. 2021, 13, 156–162. Iron-Catalyzed Vinylsilane Dimerization and Cross-Cycloadditions with 1,3-Dienes: Probing the Origins of Chemo- and Regioselectivity. C. Rose Kennedy, Matthew V. Joannou, Janelle E. Steves, Jordan M. Hoyt, Carli B. Kovel, and Paul J. Chirik ACS Catal. 2021, 11, 1368–1379. Visible-Light-Enhanced Cobalt-Catalyzed Hydrogenations: Switchable Catalysis Enabled by Divergence between Thermal and Photochemical Pathways. Lauren N. Mendelsohn, Connor S. MacNeil, Lei Tian, Yoonsu Park, Gregory D. Scholes, and Paul J. Chirik ACS Catal. 2021, 11, 1351–1360. Mechanistic Origins of Regioselectivity in Cobalt-Catalyzed C(sp2)–H Borylation of Benzoate Esters and Arylboronate Esters. Tyler P. Pabst, Linda Quach, Kaitlyn T. MacMillan, and Paul J. Chirik Chem 2021, 7, 237–254. Ligand Substitution and Electronic Structure Studies of Bis(phosphine)Cobalt Cyclooctadiene Precatalyst for Alkene Hydrogenation. Hongyu Zhong, Megan Mohadjer Beromi, and Paul J. Chirik Can. J. Chem. 2021, 99, 193–201. Determination of the N–H Bond Dissociation Free Energy in a Pyridine(diimine)molybdenum Complex Prepared by Proton-Coupled Electron Transfer. Grant W. Margulieux, Sangmin Kim, and Paul J. Chirik Inorg. Chem. 2020, 59, 15394–15401. Cobalt-Catalyzed C(sp2)–C(sp3) Suzuki–Miyaura Cross Coupling. Jacob R. Ludwig, Eric M. Simmons, Steven R. Wisniewski, and Paul J. Chirik Org. Lett. 2021, 23, 625–630. Coordination-Induced N–H Bond Weakening in a Molybdenum Pyrrolidine Complex: Isotopic Labeling Provides Insight into the Pathway for H2 Evolution. Máté J. Bezdek, István Pelczer, and Paul J. Chirik Organometallics 2020, 39, 3050–3059. Synthesis of Cationic, Dimeric alpha-Diimine Nickel Hydride Complexes and Relevance to the Polymerization of Olefins. Nadia G. Léonard, Sam Yruegas, Suzzy C. Ho, Aaron Sattler, Máté J. Bezdek, and Paul J. Chirik Organometallics 2020, 39, 2630–2635. C(sp2)–H Activation with Pyridine Dicarbene Iron Dialkyl Complexes: Hydrogen Isotope Exchange of Arenes Using Benzene-d6 as a Deuterium Source. Javier Corpas, Peter Viereck, and Paul J. Chirik ACS Catal. 2020, 10, 8640–8647. C(sp2)–H Borylation of Heterocycles by Well-Defined Bis(silylene)pyridine Cobalt(III) Precatalysts: Pincer Modification, C(sp2)–H Activation, and Catalytically Relevant Intermediates. Rebeca Arévalo, Tyler P. Pabst, and Paul J. Chirik Organometallics 2020, 39, 2763–2773. Beyond Ammonia: Nitrogen–Element Bond Forming Reactions with Coordinated Dinitrogen. Sangmin Kim, Florian Loose, and Paul J. Chirik Chem. Rev. 2020, 120, 5637–5681. Catalytic Hydrogenation of a Manganese(V) Nitride to Ammonia. Sangmin Kim, Hongyu Zhong, Yoonsu Park, Florian Loose, and Paul J. Chirik J. Am. Chem. Soc. 2020, 142, 9518–9524. Iron Catalyzed Synthesis and Chemical Recycling of Telechelic, 1,3-Enchained Oligocyclobutanes. Megan Mohadjer Beromi, C. Rose Kennedy, Jarod M. Younker, Alex E. Carpenter, Sarah J. Mattler, Joseph A. Throckmorton, and Paul J. Chirik Synthesis and Reactivity of Organometallic Intermediates Relevant to Cobalt-Catalyzed Hydroformylation. Connor S. MacNeil, Lauren N. Mendelsohn, Hongyu Zhong, Tyler P. Pabst, and Paul J. Chirik Angew. Chem. Int. Ed. 2020, 59, 8912–8916. Investigations into the Mechanism of Inter- and Intramolecular Iron-Catalyzed [2+2] Cycloaddition of Alkenes. Matthew V. Joannou, Jordan M. Hoyt, and Paul J. Chirik J. Am. Chem. Soc. 2020, 142, 5314–5330. Cobalt-Catalyzed Asymmetric Hydrogenation of alpha, beta-Unsaturated Carboxylic Acids by Homolytic H2 Cleavage. Hongyu Zhong, Michael Shevlin, and Paul J. Chirik J. Am. Chem. Soc. 2020, 142, 5272–5281. A Boron Activating Effect Enables Cobalt-Catalyzed Asymmetric Hydrogenation of Sterically Hindered Alkenes. Peter Viereck, Simon Krautwald, Tyler P. Pabst and Paul J. Chirik J. Am. Chem. Soc. 2020, 142, 3923–3930. Ketone Synthesis from Benzyldiboronates and Esters: Leveraging alpha-Boryl Carbanions for Carbon–Carbon Bond Formation. Boran Lee and Paul J. Chirik J. Am. Chem. Soc. 2020, 142, 2429–2437. Direct Observation of Transmetalation from a Neutral Boronate Ester to a Pyridine(diimine) Iron Alkoxide. Paul Peterson, Stephan Rummelt, Bradley Wile, S. Chantal Stieber, Hongyu Zhong and Paul J. Chirik Organometallics 2020, 1, 201–205. Pyridine(diimine) Iron Diene Complexes Relevant to Catalytic [2+2]-Cycloaddition Reactions. C. Rose Kennedy, Hongyu Zhong, Matthew Joannou, and Paul J. Chirik Adv. Syn. Cat. 2020, 2, 404–416.

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