Hartwig, John F. - University of California, Berkeley

个人简介

Educational Background A.B. Princeton University, 1986 Undergraduate thesis advisor: Maitland Jones Jr. Ph.D. University of California, Berkeley, 1990 Ph.D. advisors: Richard A. Anderson and Robert G. Bergman American Cancer Society Postdoctoral Fellow,Massachusetts Institute of Technology, 1990-1992 Postdoctoral advisor: Stephen J. Lippard John F. Hartwig was born outside of Chicago in 1964 and was raised in upstate New York. He received a B.A. degree in 1986 from Princeton University, and a Ph.D. degree in 1990 from the University of California, Berkeley under the collaborative direction of Robert Bergman and Richard Andersen. After an American Cancer Society postdoctoral fellowship with Stephen Lippard, he began an appointment at Yale University in 1992, where he was an Assistant Professor, Associate Professor, and then full Professor until 2004. In 2004, he was named the Irénée P. duPont Professor of Chemistry. In August of 2006, Professor Hartwig moved to the University of Illinois Urbana-Champaign, where he was named the Kenneth L. Rinehart Jr. Professor of Chemistry. In August 2011, Professor Hartwig moved to his current position on the faculty at the University of California, Berkeley, where he is the Henry Rapoport Professor of Chemistry.

研究领域

Professor Hartwig's research focuses on the discovery and understanding of new reactions catalyzed by transition metal complexes. He has developed a selective catalytic functionalization of alkanes, a method for formation of arylamines and aryl ethers from aryl halides or sulfonates, a method for the direct conversion of carbonyl compounds to alpha-aryl carbonyl derivatives, a system for the catalytic addition of amines to vinylarenes and dienes, and highly selective catalysts for the regio and enantioselective amination of allylic carbonates. With each system, his group has conducted extensive mechanistic investigations. He has revealed several new classes of reductive eliminations, has isolated discrete compounds that functionalize alkanes, and has reported unusual three-coordinate arylpalladium complexes that are intermediates in cross coupling.

近期论文

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Yu, I.F.; Manske, J.L.; Diéguez-Vázquez, A.; Misale, A.; Pashenko, A.E.; Mykhailiuk, P.K.; Ryabukhin, S.V.; Volochnyuk, D.M.; Hartwig, J.F. Catalytic undirected borylation of tertiary C–H bonds in bicyclo[1.1.1]pentanes and bicyclo[2.1.1]hexanes. Nat. Cat. 2023, 15, 685-693. Ma, S.; Hartwig, J.F. Progression of Hydroamination Catalyzed by Late Transition-Metal Complexes from Activated to Unactivated Alkenes. Acc. Chem. Res. 2023, None, ASAP. Bloomer, B.J.; Natoli, S.N.; Garcia-Borràs, M.; Pereira, J.H.; Hu, D.B.; Mechanistic and structural characterization of an iridium-containing cytochrome reveals kinetically relevant cofactor dynamics. Nature Catalysis 2023, 6, 39-51. Conk, R.J.; Hanna, S.; Shi, J.X.; Ciccia, N.R.; Qi, L.; Bloomer, B.J.; Yang, J.; Su, J.; Heuvel, S.; Wills, T.; Bell, A.T.; Hartwig, J.F. Catalytic Deconstruction of Waste Polyethylene with Ethylene to Form Propylene. Science 2022, 377, 1561-1566. Choi K, Mormino MG, Kalkman ED, Park J, Hartwig JF Palladium-Catalyzed Aryldifluoromethylation of Aryl Halides with Aryldifluoromethyl Trimethylsilanes. Angew. Chem. Int. Ed. 2022, None, ASAP. Bloomer, B.J.; Clark, D.S.; Hartwig, J.F. Progress, Challenges, and Opportunities with Artificial Metalloenzymes in Biosynthesis. Biochem. 2022, 61, ASAP. Ma, S.; Xi, Y.; Fan, H.; Roediger, S.; Hartwig, J.F. Enantioselective hydroamination of unactivated terminal alkenes. Chem 2022, 8, 535-542. Hanna, S.; Bloomer, B.; Ciccia, N.R.; Butcher, T.W.; Conk, R.J.; Hartwig, J.F. Contra-thermodynamic Olefin Isomerization by Chain-Walking Hydroboration and Dehydroboration. Org. Lett. 2022, 24, 1005-1010. Liu, Z.; Huang, J.; Gu, Y.; Clark, D.S.; Mukhopadhyay, A.; Keasling, J.D.; Hartwig, J.F. Assembly and Evolution of Artificial Metalloenzymes within E. coli Nissle 1917 for Enantioselective and Site-Selective Functionalization of C-H and C = C Bonds. J. Am. Chem. Soc. 2022, 144, 883-890. Gu, Y.; Bloomer, B.J.; Liu, Z.’ Chen, R.: Clark, D.S.; Hartwig, J.F. Directed Evolution of Artificial Metalloenzymes in Whole Cells. Angew. Chem. Int. Ed. 2022, 61, ASAP. Su, B.; Hartwig, J.F. Development of Chiral Ligands for the Transition-Metal-Catalyzed Enantioselective Silylation and Borylation of C−H Bonds. Angew. Chem. Int. Ed. 2022, 61, ASAP. Butcher, T.W.; Amberg, W.M.; Hartwig, J.F. Transition-Metal-Catalyzed Monofluoroalkylation: Strategies for the Synthesis of Alkyl Fluorides by C-C Bond Formation. Angew. Chem. Int. Ed. 2021, 60, ASAP. Sakamoto, S.; Butcher, T.W.; Yang, J.L.; Hartwig, J.F. gem-Difluoroallylation of Aryl Halides and Pseudo Halides with Difluoroallylboron Reagents in High Regioselectivity. Angew. Chem. Int. Ed. 2021, 60, 25746-25752. Huang, J.; Liu, Z.; Bloomer, B.J.; Clark, D.S.; Mukhopadhyay, A.; Keasling, J.D.; Hartwig, J.F. Unnatural Biosynthesis by an Engineered Microorganism with Heterologously Expressed Natural Enzymes and an Artificial metalloenzyme. Nat. Chem. 2021, 13, 1186-1191. Day, C.S.; Fawcett, A.; Chatterjee, R.; Hartwig, J.F. Mechanistic Investigation of the Iron-Catalyzed Azidation of Alkyl C(sp3 )−H Bonds with Zhdankin’s λ3 Azidoiodane. J. Am. Chem. Soc. 2021, 143, 16184-16196. Kalkman, E. D.; Hartwig, J. F. Direct Observation of Diastereomeric α-C-Bound Enolates during Enantioselective α-Arylations: Synthesis, Characterization, and Reactivity of Arylpalladium Fluorooxindole Complexes. J. Am. Chem. Soc. 2021, 143, 11741-11750. Fuentes, M. A.; Gava, R.; Saper, N. I.; Romero, E.; Caballero, A.; Hartwig, J. F.; Pérez, P. J. Copper-Catalyzed Dehydrogenative Amidation of Light Alkanes. Angew. Chem. Int. Ed. 2021, 60, 18467-18471. Chen, L.; Malollari, K.G.; Ullana, A.; Hartwig, J.F. Ruthenium-Catalyzed, Chemoselective and Regioselective Oxidation of Polyisobutene. J. Am. Chem. Soc. 2021, 143, 4531-4535. Fawcett, A.; Keller, M.J.; Herrera, Z.; Hartwig, J.F. Site Selective Chlorination of C(sp3)-H Bonds Suitable for Late-Stage Functionalization. Angew. Chem. Int. Ed. 2021, 60, 8276-8283. Ray, R.; Hartwig, J.F. Oxalohydrazide Ligands for Copper-Catalyzed C−O Coupling Reactions with High Turnover Numbers. Angew. Chem. Int. Ed. 2021, 60, 8203-8211. Ji, P.; Park, J.; Gu, Y.; Clark, D.S.; Hartwig, J.F. Abiotic reduction of ketones with silanes catalysed by carbonic anhydrase through an enzymatic zinc hydride. Nat. Chem. 2021, 13, 312-318. Chen, L.; Malollari, K.G.; Uliana, A.; Sanchez, D.; Messersmith, P.B.; Hartwig, J.F. Selective, Catalytic Oxidations of C–H Bonds in Polyethylenes Produce Functional Materials with Enhanced Adhesion. Chem 2021, 7, 137-145. Tlahuext-Aca, A.; Lee, S. Y.; Sakamoto, S.; Hartwig, J.F. Direct Arylation of Simple Arenes with Aryl Bromides by Synergistic Silver and Palladium Catalysis. ACS Catal. 2021, 11, 1430-1434. Tlahuext-Aca, A.; Hartwig, J.F. Site-Selective Silver-Catalyzed C–H Bond Deuteration of Five-Membered Aromatic Heterocycles and Pharmaceuticals. ACS Catal. 2021, 11, 1119-1127. Ma, S.; Hill, C.K.; Olen, C.L.; Hartwig, J.F. Ruthenium-Catalyzed Hydroamination of Unactivated Terminal Alkenes with Stoichiometric Amounts of Alkene and an Ammonia Surrogate by Sequential Oxidation and Reduction. J. Am. Chem. Soc. 2021, 143, 359-368. Xi, Y.; Ma, S.; Hartwig, J.F. Catalytic asymmetric addition of an amine N–H bond across internal alkenes. Nature 2020, 588, 254-260. Qiu, Y.; Hartwig, J.F. Mechanism of Ni-Catalyzed Oxidations of Unactivated C(sp3)–H Bonds. J. Am. Chem. Soc. 2020, 142, 19239-19248. Wang, J.Y.; Choi, K.; Zuend, S.J.; Borate, K.; Hartwig, J.F. Cross-Coupling between Hydrazine and Aryl Halides with Hydroxide Base at Low Loadings of Palladium by Rate-Determining Deprotonation of Bound Hydrazine. Angew. Chem. Int. Ed. 2020, 60, 399-408. Oeschger, R.; Su, B.; Yu, I.; Ehinger, C.; Romero, E.; He, S.; Hartwig, J.F. Diverse functionalization of strong alkyl C–H bonds by undirected borylation. Science 2020, 368, 736-741. Xi, Y.; Su, B.; Qi, X.; Pedram, S.; Liu, P.; Hartwig, J.F. Application of Trimethylgermanyl-Substituted Bisphosphine Ligands with Enhanced Dispersion Interactions to Copper-Catalyzed Hydroboration of Disubstituted Alkenes. J. Am. Chem. Soc. 2020, 142, 18213-18222. Richers, C.P.; Roediger, S.; Laserna, V.; Hartwig, J.F. Effects of Ligands on the Migratory Insertion of Alkenes into Rhodium–Oxygen Bonds. Chem. Sci. 2020, 11, 10449-10456. Butcher, T.W.; Yang, J.L.; Hartwig, J.F. Copper-Catalyzed Defluorinative Borylation and Silylation of gem-Difluoroallyl Groups. Org. Lett. 2020, 22, 6805-6809. Hartwig, J.F.; Shaughnessy, K.H.; Shekhar, S.; Green, R.A. Palladium-Catalyzed Amination of Aryl Halides. Organic Reactions 2020, 100, 853-943. Hanna, S.; Wills, T.; Butcher, T.W.; Hartwig, J.F. Palladium-Catalyzed Oxidative Dehydrosilylation for Contra-Thermodynamic Olefin Isomerization. ACS Catal. 2020, 10, 8736-8741. Butcher, T.W.; Yang, J.L.; Amberg, W.M.; Watkins, N.B.; Wilkinson, N.D.; Hartwig, J.F. Desymmetrization of difluoromethylene groups by C-F bond activation. Nature 2020, 583, 548-553. Karmel, C.; Hartwig, J.F. Mechanism of the Iridium-Catalyzed Silylation of Aromatic C–H Bonds. J. Am. Chem. Soc. 2020, 142, 10494-10505. Buchwald, S.L.; Hartwig, J.F. In Praise of Basic Research as a Vehicle to Practical Applications: Palladium-Catalyzed Coupling to Form Carbon-Nitrogen Bonds. Isr. J. Chem. 2020, 60, 177-179. Su, B; Bunescu, A.; Qiu, Y.; Zuend, S.J.; Ernst, M.; Hartwig, J.F. Palladium-Catalyzed Oxidation of β-C(sp3)–H Bonds of Primary Alkylamines through a Rare Four-Membered Palladacycle Intermediate. J. Am. Chem. Soc. 2020, 142, 7912-7919. Saper, N.I.; Ohgi, A.; Small, D.W.; Semba, K.; Nakao, Y.; Hartwig, J.F. Nickel-catalyzed anti-Markovnikov hydroarylation of unactivated alkenes with unactivated arenes facilitated by non-covalent interactions. Nat. Chem. 2020, 12, 276-283. Larsen, M.A.; Oeschger, R.J.; Hartwig, J.F. Effect of Ligand Structure on the Electron Density and Activity of Iridium Catalysts for the Borylation of Alkanes. ACS Catal. 2020, 10, 3415-3424. Dorel, R.; Boehm, P.; Schwinger, D.P.; Hartwig, J.F. Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride. Chem. Eur. J. 2020, 26, 1759-1762. Yoritate, M.; Londregan, A.T.; Lian, Y.; Hartwig, J.F. Sequential Xanthalation and O‑Trifluoromethylation of Phenols: A Procedure for the Synthesis of Aryl Trifluoromethyl Ethers. J. Org. Chem. 2019, 84, 15767-15776. Karmel, C.; Rubel, C.Z.; Kharitonova, E.V.; Hartwig, J.F. Iridium‐Catalyzed Silylation of Five‐Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl‐Imidazoline Ligand. Angew. Chem. Int. Ed. 2020, 59, 6074-6081. Oeschger, R.J.; Larsen, M.A.; Bismuto, A.; Hartwig, J.F. Origin of the Difference in Reactivity between Ir Catalysts for the Borylation of C-H Bonds. J. Am. Chem. Soc. 2019, 141, 16479-16485. He, Z.; Hartwig, J.F. Palladium-catalyzed α-arylation for the addition of small rings to aromatic compounds. Nat. Comm. 2019, 10, 1-4. Kalkman, E.D.; Mormino, M.G.; Hartwig, J.F. Unusual Electronic Effects of Ancillary Ligands on the Perfluoroalkylation of Aryl Iodides and Bromides Mediated by Copper(I) Pentafluoroethyl Complexes of Substituted Bipyridines. J. Am. Chem. Soc. 2019, 141, 19458-19465. Hartwig, J.F.; Ward, T.R. New ‘Cats’ in the House: Chemistry Meets Biology in Artificial Metalloenzymes and Repurposed Metalloenzymes. Acc. Chem. Res. 2019, 52, 1145-1145. Hanna, S., Butcher, T.W., Hartwig, J.F. Contra-thermodynamic Olefin Isomerization by Chain-Walking Hydrofunctionalization and Formal Retro-hydrofunctionalization. Org. Lett. 2019, 21, 7129-7133. Gu, Y., Natoli, S.N., Liu, Z., Clark, D.S., Hartwig, J.F. Site-Selective Functionalization of (sp3)C-H Bonds Catalyzed by Artificial Metalloenzymes Containing an Iridium-Porphyrin Cofactor. Angew. Chem. Int. Ed. 2019, 58, 13954-13960. He, Z.T., Jiang, X., Hartwig, J.F. Stereodivergent Construction of Tertiary Fluorides in Vicinal Stereogenic Pairs by Allylic Substitution with Iridium and Copper Catalysts. J. Am. Chem. Soc. 2019, 141, 13066-13073. He, Z.T., Hartwig, J.F. Palladium-Catalyzed α-Arylation of Carboxylic Acids and Secondary Amides via a Traceless Protecting Strategy. J. Am. Chem. Soc. 2019, 141, 11749-11753. Hartwig, J.F., Romero, E.A. Iridium-catalyzed silylation of unactivated C-H bonds. Tetrahedron 2019, 75, 4059-4070. Karmel, C., Chen, Z., Hartwig, J.F. Iridium-Catalyzed Silylation of C–H Bonds in Unactivated Arenes: A Sterically Encumbered Phenanthroline Ligand Accelerates Catalysis. J. Am. Chem. Soc. 2019, 141, 7063-7072. Hanna, S., Holder, J.C., Hartwig, J.F. A Multicatalytic Approach to the Hydroaminomethylation of α-Olefins. Angew. Chem. Int. Ed. 2019, 58, 3368-3372. Haydl, A.M., Hartwig, J.F. Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters. Org. Lett. 2019, 21, 1337-1341. He, Z.T., Hartwig, J.F. Enantioselective α-functionaliations of ketones via allylic substitution of silyl enol ethers. Nat. Chem. 2019, 11, 177. Natoli, S.N., Hartwig, J.F. Noble-Metal Substitution in Hemoproteins: An Emerging Strategy for Abiological Catalysis. Acc. Chem. Res. 2019, 52, 326-335. Jiang, Q., Peacock, D.M., Hartwig, J.F., Cundari, T.R. Carbon (sp3)-nitrogen bond-forming reductive elimination from phosphine-ligated alkylpalladium (II) amide complexes: A DFT study. Tetrahedron 2019, 75, 137-143.