Jack R. Norton

Jack R. Norton

Research Interest

Inorganic
Organic

Summary

Our theme is catalysis, but our research interests span many different areas of organometallic chemistry. We approach problems in a mechanistic way, use a variety of physical methods to investigate reaction mechanisms, and apply organometallic chemistry to the synthesis of organic compounds.

For example, we use transition-metal hydrides to catalyze the generation of organic radicals from hydrogen gas and appropriate olefins. Tin hydrides have traditionally been used as stoichiometric H• donors in radical reactions, but their byproducts are toxic and difficult to remove. Our reaction is proving useful for radical cyclizations, particularly cycloisomerizations.

We have reported the asymmetric synthesis of a-amino acid amides and esters by the dynamic kinetic resolution (or “asymmetric transformation”) of zirconaaziridines with chiral carbonates. The stereochemical outcome depends upon the rate of configuration change of the zirconaaziridine carbon.

We are also:

  • Investigating the mechanism of isocyanide (RNC) insertion into metal-carbon bonds. We hope to devise a method of catalyzing the 4 + 1 cycloaddition of dienes to isocyanides.
  • Attempting to use copper hydrides in catalyzing the generation of electricity from hydrogen gas

Recent Awards

ACS Cope Scholar Award, Sierra Nevada Distinguished Chemist, ACS Organometallic Award

“Electron Transfer from Hexameric Copper Hydrides”, M. Eberhart, J. R. Norton, A. Zuzek, W. Sattler, S. Ruccolo, J. Am. Chem. Soc. 2013, 135, 17262–17265. DOI: 10.1021/ja408925m

“The Effect of Double Bond Substituents on the Rate of Cyclization of a-Carbomethoxy Hex-5-enyl Radicals”, A. Han, T. Spataru, J. Hartung, G. Li, J. R. Norton, J. Org. Chem. 2014, 79, 1938–1946. DOI: 10.1021/jo402499w

“Kinetics and Thermodynamics of H−/H•/H+ Transfer from a Rhodium(III) Hydride”, Y. Hu, J. R Norton, J. Am. Chem. Soc. 2014, 136, 5938–5948.

“Formation and Properties of a Cobalt Hydride from Cobaloximes and Hydrogen”, D. P. Estes, D. C. Grills, J. R. Norton, J. Am. Chem. Soc. 2014, 136, 17362–17365.

“Dihydrogen Activation by Cobaloximes with Various Axial Ligands”, G. Li, D. P. Estes, J. R. Norton, A. Sattler, S. Ruccolo, Inorg. Chem. 2014, 53,            10743–10747.

“Direct Generation of Oxygen-Stabilized Radicals by H• Transfer from Transition Metal Hydrides”, J. L. Kuo, J. Hartung, A. Han, J. R. Norton, J. Am. Chem. Soc. 2015, 137, 1036–1039.

“Radical Isomerization and Cycloisomerization Initiated by H• Transfer,” G. Li, J. L. Kuo, A. Han, J. M. Abuyuan, L. C. Young, J. R. Norton, J. H. Palmer, J. Am. Chem. Soc. 2016, 138, 7698–7704.

“Reaction of Cp*(Cl)M(Diene) (M = Ti, Hf) with Isonitriles”, T. N. Valadez, J. R. Norton, and M. C. Neary, J. Am. Chem. Soc. 2015, 137, 10152–10155. DOI: 10.1021/jacs.5b06654.

“Synthesis and Resolution of Chiral Ruthenium Complexes Containing the 1-Me-3-PhCp Ligand,” Y. Hu, A. P. Shaw, H. Guan, J. R. Norton, W. Sattler, Y. Rong, Organometallics 2016, 35, 39–46. DOI:10.1021/acs.organomet.5b00852

“Transition-Metal Hydride Radical Cations,” Y. Hu, A. P. Shaw, D. P. Estes, and J. R. Norton, Chem. Rev. 2016, 116, 8427–8462. DOI:10.1021/acs.chemrev.5b00532

“Reaction of Cp*Zr(2,3-dimethylbutadiene) with Isonitriles and CO,” T. N. Valadez, J. R. Norton, M. C. Neary, and P. J. Quinlivan, Organometallics 2016, 35, 3163–3169. DOI: 10.1021/acs.organomet.6b00522

“Cationic Hydride Clusters Arising from Oxidation of (Ph3P)6Cu6H6,” S. Liu, M. Eberhart, J. R. Norton, X. Yin, M. Neary, and D. W. Paley, J. Am. Chem. Soc. 2017, 139, 7685-7688. DOI: 10.1021/jacs.7b02183

“Radical Cyclizations from Alkyl Iodides under H2: Catalysis by [CpV(CO)3H]–,” Jonathan L. Kuo, Chris Lorenc, Janine M. Abuyuan, and Jack R. Norton. J. Am. Chem. Soc 2018, 140 (13), 4512 – 4516. DOI: 10.1021/jacs.8b02119

“The Insertion of Isonitriles into the M-C Bonds of Group 4 Dialkyl,” Jiawei Chen, Nadine Yassin, Thilina Gunasekara, Jack R. Norton, and Michael Rauch. J. Am. Chem. Soc 2018, 140 (28), 8980 – 8989. DOI: 10.1021/jacs.8b02119

“Insertion of Isonitriles into the Zr–CH3 Bond of Cp*2Zr(CH3)2 and Electrophilic Cleavage of the Remaining Methyl Group,” Jiawei Chen, Tao Chen, Jack R. Norton, and Michael Rauch. Organometallics 2018, 37 (23), 4424-4430 DOI: 10.1021/acs.organomet.8b00690

“TEMPO–Mediated Catalysis of the Sterically Hindered Hydrogen Atom Transfer Reaction between (C5Ph5)Cr(CO)3H and a Trityl Radical,” Thilina Gunasekara, Graham P. Abramo, Andreas Hansen, Hagen Neugebauer, Markus Bursch, Stefan Grimme, and Jack R. Norton, submitted to J. Am. Chem. Soc.

“Anti-Markovnikov Alcohols by Epoxide Hydrogenation through Cooperative Catalysis,” Chengbo Yao, Tobias Dahmen, Andreas Gansäuer, and Jack R. Norton, submitted to Science.

"Thermodynamics of H+/H•/H–/e– Transfer from [CpV(CO)3H]−: Comparisons to the Isoelectronic CpCr(CO)3H," Jonathan L. Kuo, Thilina Gunasekara, Andreas Hansen, Hunter B. Vibbert, Fabian Bohle, Jack R. Norton, Stefan Grimme, and Patrick J. Quinlivan. Organometallics 2019, 38 (21), 4319 - 4328. DOI: 10.1021/acs.organomet.9b00586 

"H· Transfer-Initiated Synthesis of γ-Lactams: Interpretation of Cycloisomerization and Hydrogenation Ratios," Chris Lorenc, Hunter B. Vibbert, Chengbo Yao, Jack R. Norton, and Michael Rauch. ACS Catalysis 2019, 9 (11), 10294 - 10298. DOI: 10.1021/acscatal.9b03678 

"Catalyzing the Hydrodefluorination of CF3-Substituted Alkenes by PhSiH3. H• Transfer from a Nickel Hydride," Chengbo Yao, Shuai Wang, Jack R. Norton, and Matthew Hammond. J. Am. Chem. Soc. 2020, 142, 4793–4799. DOI: https://doi.org/10.1021/jacs.9b13757 

“Catalytic Radical Cycloisomerization onto a Carbonyl Oxygen,” Shicheng Shi, Jonathan L. Kuo, Tao Chen, Jack R. Norton. Org. Lett. 2020, 22(15), 6171–6176. 
DOI: 10.1021/acs.orglett.0c02272 

“Synthesis, Characterization, and Catalytic Activity of Bimetallic Ti/Cr Complexes,” Jiawei Chen, Hunter B. Vibbert, Chengbo Yao, Amymarie K. Bartholomew, Alexander P. Aydt, Steffen Jockush, Jack R. Norton, Matthew Hammond, Michael Rauch, Organometallics 2020, 39, 4592-4598. DOI: 10.1021/acs.organomet.0c00645 

“Hydrogen Atom Transfer Rates from Tp-Containing Metal-Hydrides to Trityl Radicals,” Hunter B. Vibbert, Hagen Neugebauer, Jack R. Norton, Andreas Hansen, Markus Bursch, Stefan Grimme, Canadian Journal of Chemistry 2020, 99, 216-220. DOI: 10.1139/cjc-2020-0392 

“Highly Selective Hydrogenation of C=C Bonds Catalyzed by a Rhodium Hydride” Yiting Gu, Jack R. Norton, Farbod Salahi, Vladislav G. Lisnyak, Zhiyao Zhou, Scott A. Snyder, J. Am. Chem. Soc. 2021, 143(25) 9657-9663. DOI: 10.1021/jacs.1c04683 

“Generation of a-Boryl Radicals by H- Transfer and their Use in Cycloisomerizations,” Shicheng Shi, Farbod Salahi, Hunter B. Vibbert, Maleeha Rahman, Scott A. Snyder, Jack R. Norton, Angew. Chem. Int. Ed. Engl. 2021, 60(42), 22678-22682. DOI: 10.1002/anie.202107665 

“A Programmable Synthesis of Diverse Terpene Architectures from Phenols,” Farbod Salahi, Chengbo Yao, Jack R. Norton, Scott A. Snyder, 2021. DOI: 10.33774/chemrxiv-2021-m5q24