Knowles, Robert R. - Princeton University

个人简介

A native of Virginia’s Shenandoah Valley, Rob received a B.S in chemistry from the College of William and Mary in 2003. He went on to receive his PhD in synthetic organic chemistry from Caltech in 2008 for his work on natural product synthesis in the labs of Dave MacMillan. Following his doctoral work, Rob moved to Eric Jacobsen’s lab at Harvard University as a NIH postdoctoral fellow, where his work focused on asymmetric catalysis and new reaction development. Rob joined the Department of Chemistry at Princeton University in the summer of 2011, where his group’s work has focused primarily on the applications of proton-coupled electron transfer (PCET) in organic synthesis. In 2017, he was promoted to Professor of Chemistry. EMPLOYMENT Professor of Chemistry, Princeton University Mar. 2017 – present Assistant Professor of Chemistry, Princeton University July 2011 – Mar. 2017 NIH NRSA Postdoctoral Fellow, Harvard University Advisor: Eric Jacobsen EDUCATION Dec. 2008 – June 2011 Doctor of Philosophy, California Institute of Technology Advisor: David MacMillan July 2003 – Oct. 2008 Bachelor of Science in Chemistry, College of William and Mary Advisors: Robert Hinkle and David Kranbuehl Sep. 1999 – May 2003

研究领域

Our lab is interested in addressing unsolved problems in synthetic organic chemistry and asymmetric catalysis. One area of recent focus has been exploring the synthetic applications of proton-coupled electron transfer (PCET) reactions. PCETs are unconventional redox processes in which an electron and proton are exchanged together in a concerted elementary step. While these mechanisms are recognized to play a central a role in biological redox catalysis and inorganic solar energy conversion technologies, their applications in synthetic organic chemistry remain largely unexplored.

近期论文

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Light-driven Deracemization Enabled by Excited-State Electron Transfer. Shin, N. Y.; Ryss, J. M.; Zhang, X.; Miller, S. J.; Knowles, R. R. Science, 2019, 366, 364–369. Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines. Miller, D. C.; Ganley, J. M.; Musacchio, A. J.; Sherwood, T. C.; Ewing, W. R.; Knowles, R. R. J. Am. Chem. Soc. 2019, 141, accepted.(doi: 10.1021/jacs.9b08746). Understanding Chemoselectivity in Proton-Coupled Electron Transfer: A Kinetic Study of Amide and Thiol Activation. Qui, G.; R.; Knowles, R. R. J. Am. Chem. Soc. 2019, 141, accepted. (doi: 10.1021/jacs.9b08398). C-H Alkylation via Multisite Proton-Coupled Electron Transfer of an Aliphatic C-H Bond. Morton, C. M.; Zhu,Q.; Ripberger, H.; Troian-Gauthier, L; Toa, Z. S. D.; Knowles, R. R.; Alexanian, E. J. J. Am. Chem. Soc. 2019,141, 13253–13260. Catalytic Ring Expansions of Cyclic Alcohols Enabled by Proton-Coupled Electron Transfer. Zhao, K.; Yamashita, K.; Carpenter, J.; Sherwood, T. C.; Ewing, W. R.; Cheng, P. T. W.; Knowles, R. R. J. Am. Chem. Soc. 2019, 141,8752–8757. PCET-Enabled Olefin Hydroamidation Reactions with N-Alkyl Amides. Nguyen, S. T.; Zhu, Q.; Knowles, R. R. ACS Catalysis 2019, 9, 4502–4507. Evaluation of Excited State Bond Weakening for Ammonia Synthesis from a Manganese Nitride: Stepwise Proton-Coupled Electron Transfer is Preferred Over Hydrogen Atom Transfer. Loose, F.; Wang, D.; Tian, L.;Scholes, G. D.; Knowles, R. R.; Chirik, P. J. Chem. Comm. 2019, 55, 5595–5598. Decarboxylative Intramolecular Arene Alkylation Using N-(Acyloxy)phthalimides, as Organic Photocatalyst, and Visible Light. Sherwood, T. C.; Xiao, H.-Y.; Bhaskar, R. G.; Simmons, E. M.; Zaretsky, S.; Rauch, M. P.; Knowles, R. R. and Dhar, T. G. M. J. Org. Chem. 2019, 84, 8360–8379. N–H Bond Formation in a Manganese(V) Nitride Yields Ammonia by Light-Driven Proton-Coupled Electron Transfer. Wang, D.; Loose, F.; Chirik, P. J.; Knowles, R. R. J. Am. Chem. Soc. 2019, 141, 4795–4799. Rate-Driving Force Relationships in the Multisite PCET Activation of Ketones. Qui, G.; R.; Knowles, R. R. J. Am. Chem. Soc. 2019, 141, 2721-2730. A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C–C Bond Cleavage Reactions. Ota, E.; Wang, H.; Frye, N. L.; R.; Knowles, R. R. J. Am. Chem. Soc. 2019, 141, 1457–1462. Applications of and Prospects for Triplet-Triplet Annihilation Photon Upconversion. Rauch, M. P.; R.; Knowles, R. R. CHIMIA. 2018, 72, 501–507. (Laureate Article for Grammaticakis-Neumann Prize) Enantioselective Synthesis of Pyrroloindolines via Non-Covalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products. Gentry, E. C.; Rono, L. J.; Hale, M. E.; Matsuura, R.; Knowles, R. R. J. Am. Chem. Soc. 2018, 140, 3394–3402. Intermolecular Anti-Markovnikov Hydroamination of Unactivated Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer. Zhu, Q.; Graf, D. E.; Knowles, R. R. J. Am. Chem. Soc. 2018, 140, 741–747. Catalytic Intermolecular Hydroaminations of Unactivated Olefins with Secondary Alkyl Amines. Musacchio, A. J.; Lainhart, B. C.; Zhang, X.; Naguib, S. G.; Sherwood, T. C.; Knowles, R. R. Science, 2017, 355, 727–730. Catalytic Alkylation of Remote C-H Bonds Enabled by Proton-Coupled Electron Transfer. Choi, G. C.; Zhu, Q.; Miller, D. C.; Gu, C. J.; Knowles, R. R. Nature, 2016, 539, 268–271. Catalytic Ring-Opening of Cyclic Alcohols Enabled by PCET Activation of Strong O-H Bonds. Yayla, H. G.; Wang, H.; Tarantino, K. T.; Orbe, H. S.; Knowles, R. R. J. Am. Chem. Soc. 2016, 138, 10794–10797. Synthetic Applications of Proton-Coupled Electron Transfer. Gentry, E. C.; Knowles, R. R. Acc. Chem. Res.2016, 49, 1546–1556. Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations. Zhu, Q.;Gentry, E. C.; Knowles, R. R. Angew. Chem. Int. Ed. 2016, 55, 9969–9973. Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications and Opportunities. Miller,D. C.; Tarantino, K. T.; Knowles R. R. Topics in Current Chemistry 2016, 374 (30), 145–203.DOI:10.1007/s41061-016-0030-6.