Gutierrez, Osvaldo - Texas A&M University

个人简介

About Osvaldo Osvaldo was born in Salamanca, Guanajuato (Mexico) and raised in Sacramento, California. He attended Sacramento City College for 6 years then transferred to UCLA in 2006 to pursue a career in medicine. However, working as an undergraduate at the laboratories of Prof. Kendall N. Houk inspired him to change career path to organic chemistry. He graduated in 2009 with B.S. and M.S. degrees in chemistry from UCLA and moved back to northern California to enroll in graduate studies at UC Davis. He completed his PhD in 2012 under the guidance of Prof. Dean J. Tantillo; his thesis was focused on the use of computational electronic structure methods to reveal mechanisms of catalytic processes. He then moved across the country to work with Prof. Marisa C. Kozlowski at the University of Pennsylvania where he used computational and experimental tools to study transition-metal catalyzed processes. In his free time, he likes to listen to 90s rap and enjoy time with his two daughters and wife. In 2016, he joined the faculty of the University of Maryland-College Park as an Assistant Professor and promoted to Associate Professor with tenure. In 2021, he was appointed Associate Professor at Texas A&M University. He is recipient of the NSF CAREER Award (2018), the NIH NIGMS Maximizing Investigator's Research Award (2020), and was recently named as part of the C&EN Talented 12 (2020) and Camille Dreyfus Teacher Scholar. Education and Training Postdoctoral Fellow, University of Pennsylvania, Organic/Organometallic Chemistry, 2012-2016 Advisor: Professor Marisa C. Kozlowski Ph.D., University of California-Davis, Physical Organic Chemistry, 2009-2012 Advisor: Professor Dean J. Tantillo B.S. and M.S., University of California-Los Angeles, Organic Chemistry, 2006-2009 Advisor: Professor Kendall N. Houk Sacramento City College, Chemistry, 2001-2006 Professional History Associate Professor, Texas A&M University, Department of Chemistry, August 2021-present Associate Professor, University of Maryland-College Park, Department of Chemistry and Biochemistry,July 2021-August 2021 Nathan Drake Assistant Professor, University of Maryland-College Park, Department of Chemistry and Biochemistry, July 2019-2021 Assistant Professor, University of Maryland-College Park, Department of Chemistry and Biochemistry,June 2016-2019

研究领域

Research Motivation: Despite advances in high-throughput screening methods leading to a surge in the discovery of catalytic reactions, our knowledge of the molecular-level interactions in the rate- and selectivity-determining steps of catalytic reactions involving highly unstable and reactive open-shell intermediates is rudimentary. These knowledge gaps prevent control, suppression or enhancement, of competing reaction channels that can drive the development of new catalytic reactions. Research Approach: The Gutierrez group combines computational and experimental approaches to advance our understanding of organic/organometallic reaction mechanisms. In turn, this information is used to guide the design of new sustainable, catalytic, and asymmetric transformations that can be adapted by the organic, organometallic, and bio(in)organic in the synthesis of medicinally-active compounds.

近期论文

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Alvarez, E. M.; Ullah, M.; Stewart, G.; Lalisse, R.; Gutierrez, O.; Malapit, C. A. "Site-selective electrochemical arene C–H amination" J. Am. Chem. Soc. 2024, 146, in press. Wu, F.-W.; Chintawar, C. C.; Lalisse, R.; Mukherjee, P.; Dutta, S.; Tyler, J.; Daniluc, C. G.; Gutierrez, O.;# Glorius, F.# Nature Catal. 2024, In PRESS: DOI 10.1038/s41929-023-01089-x “Ring expansion of indene by photoredox-enabled functionalized carbon-atom insertion” Lin, L. Q.; Rentería-Gómez, A.; Martin, R.; Ong, K. Z. W.; Parris, A.; Gutierrez, O.;#Koh, M. J.# Angew. Chem. Int. Ed. 2024, e202317935 “Selective1,2-Hydroarylation(Alkenylation)ofgem-Difluoroalkenesto Access(CF2H) Motifs” Mandal, H.; Ogunyemi, O.; Nicholson, J.; Orr, M. E.; Lalisse, R. F.; Rentería-Gómez, Á.; Gogoi, A. R.; Gutierrez, O.;# Michaudel, Q.; Goodson III, T.# J. Phys. Chem. C. 2024, in press. “Linear and Nonlinear Optical Properties of All-cis and All-trans Poly(p-phenylene vinylene) ” Youshaw, C. R.; Yang, M.-H.; Gogoi, A. R.; Rentería-Gómez, Á.; Liu, L.; Morehead, L. K.; Gutierrez, O.;# Org. Lett. 2023, 25, 8320-8325.“Iron-Catalyzed Enantioselective Multicomponent Cross-Couplings of a-Boryl Radicals” Sar, D.; Yin, S.;* Grygus, J.;* Rentería-Gómez, Á.;* Garcia, M.; Gutierrez, O.# Chem. Sci. 2023, in print. doi.org/10.1039/D3SC04549H. “Expanding Chemical Space of Enol Silyl Ethers: Catalytic Dicarbofunctionalization Enabled by Iron Catalysis” Usman, F. O.; Gogoi, A. R.; Mixdorf, J. C.; Gutierrez, O.;# Nguyen, H. N.# Angew. Chem. Int. Ed. 2023, ASAP. doi.org/10.1002/anie.202314843“Rhodium-Catalyzed Asymmetric Synthesis of 1,2-Disubstituted Allylic Fluorides” Renteria-Gomez, A.; Guerrero, M.;* Ramirez-Lopez, M.;* Gutierrez, O.# Org. Lett. 2023, 25, 7440-7445.“Regioselective Fluoroalkylarylation of Enamides Enabled by an Iron-Catalyzed Multicomponent Radical Cross-Coupling Stategy” Andreettta, P.; Martin, R. T.; Souliah, C.; Rentería-Gómez, Á.; Song, Z.; Khorramshashi Bayat, Y.; Ivlev, S.; Gutierrez, O.;# Casitas, A.# Angew. Chem. Int. Ed. 2023, in print. doi.org/10.1002/anie.202310129“Experimental and Computational Studies on Cobalt(I)-Catalyzed Regioselective Allylic Alkylation Reactions” Aguilera, M. C.; Gogoi, A. R.; Lee, W.; Liu, L.; Brennessel, W.; Gutierrez, O.;# Neidig, M. L.# ACS Catal. 2023, 13, 8987-8996..“Insight into Radical Initiation, Solvent Effects and Biphenyl Production in Iron-Bisphosphine Cross-Couplings” Crockett, M. P.; Piña, J.; Gogoi, A. R.; Lalisse, R. F.; Nguyen, A. V.; Gutierrez, O.#; Thomas, A. A.# J. Am. Chem. Soc. 2023, 145, 10743–10755.“Breaking the tert-Butyllithium Contact Ion Pair: A Gateway to Alternate Selectivity in Lithiation Reactions” Peng, Q.; Gogoi, A. R.; Renteria-Gomez, A.; Gutierrez, O.#; Scheidt, K. A.# Chem 2023, 9, 1983-1993.“Visible Light-Induced Coupling of Carboxylic Acids with Alcohols/Amines via Phosphorous Linchpin Strategy” Day, C. S.; Renteria-Gomez, A.; Ton, S. J.; Gogoi, A.; Gutierrez, O.;# Martin, R.# Nat. Catal. 2023, 6, 244-253.“Elucidating Electron Transfer Events in Polypyridine Nickel Complexes” Zhou, M.; Tsien, J.; Dykstra, R.; Hughes, J. M.; Peters, B. K.; Merchant, R. R.; Gutierrez, O.#; Quin, T.# Nat. Chem. 2023, 15, 550-559.“Alkyl Sulfinates as Cross-Coupling Partners: Programmable and Stereospecific Installation of C(sp3) Bioisosteres” Yang, Y.; Tsien, J.; Dykstra, R.; Chen, S.-J.; Wang, J. B.; Merchant, R. R.; Hughes, J. M. E.; Peters, B. K. Gutierrez, O.#; Quin, T.# Nat. Chem. 2023, In press. doi.org/10.1038/s41557-023-01342-7“Exploring Uncharted Chemical Space: Programmable Late-Stage Functionalization of Bridge-substituted BCP bis-Boronates” Matsuo, B.; Majhi, J.; Granados, A.; Sharique, M.; Martin, R. T.; Gutierrez, O.#; Molander, G. A.# Chem. Sci. 2023, 14, 2379-2385.“Transition metal-free photochemical C–F activation for the preparation of difluorinated-oxindole derivatives” Zhu, J. L.; Schull, C. R.; Tam, A. T.; Renteria-Gomez, A.; Gogoi, A. R.; Gutierrez, O.#; Scheidt, K. A.# J. Am. Chem. Soc. 2023, 145, 1535-1541.“Photoinduced Acylations Via Azolium-Promoted Intermolecular Hydrogen Atom Transfer” Dherange, B. D.; Yuan, M.; Kelly, C. B.;# Reiher, C. A.; Grosanu, C.; Berger, K. J.; Gutierrez, O.;# Levin, M.# J. Am. Chem. Soc. 2023, 145, 17-24.“Direct Deaminative Functionalization” Li, X.; Yuan, M.; Chen, F.; Quing, F.-L.; Gutierrez, O.;# Chu, L.# Chem 2023, 9, 154-169.“Three-component enantioselective alkenylation of organophosphonates via nickel metallaphotoredox catalysis” Tan.; G.; Paulus, F.;Renteria-Gomez, A.; Lalisse, R.F.; Daniliuc, C. G.; Gutierrez, O.#; Glorius, F.# J. Am. Chem. Soc. 2022, 144, 21664-21673. Dhungana, R. K.; Granados, A.; Ciccone, V.; Martin, R. T.; Majhi, J.; Sharique, M.; Gutierrez, O.#; Molander, G. A.# ACS Catal. 2022, 12, 15750-15757.“Trifunctionalization of Cinnamyl Alcohols Provides Access to Brominated a,a-Difluoro-g-Lactones via Photoinduced Radical-Polar-Radical Mechanism” Altundas, B.; Alwedi, E.; Song, Z.; Gogoi, A. R.; Dykstra, R.; Gutierrez, O.;# Fleming, F. F.# Nat. Commun. 2022, 13, 6444.“Dearomatization of Aromatic Asmic Isocyanides to Complex Cyclohexadienes” Renteria-Gomez, A.;* Lee, W.;* Yin, S.; Davis, M.; Gogoi, A. R; Gutierrez, O.# ACS Catal. 2022, 12, 11547-11556.“General and Practical Route to Diverse 1-(Difluoro)alkyl-3-aryl Bicyclo[1.1.1]pentanes Enabled by an Fe-Catalyzed Multicomponent Radical Cross-Coupling Reaction” Majhi, J.; Dhungana, R. K.; Renteria-Gomez, A.; Sharique, M.; Li, Dong, W.; Gutierrez, O.#; Molander, G. A.# J. Am. Chem. Soc. 2022, 144, 15871-15878.“Metal-Free Photochemical Imino-Alkylation of Alkenes with Bifunctional Oxime Esters” Wen, Y.; Renteria-Gomez, A.; Day, G. S.; Smith, M. F.; Yan, T-H.; Osman K., R.; Gutierrez, O.# Sharma, V. K.; # Ma, X.; # Zhou, H.-C.# J. Am. Chem. Soc. 2022, 144, 11840-11850.“Integrated Photocatalytic Reduction and Oxidation of Perfluorooctanoic Acid by Metal–Organic Frameworks: Key Insights into the Degradation Mechanisms.” Rotella, M. E.; Sar, D.; Liu, L.; Gutierrez, O.# Chem. Commun. 2021, 57, 12508-12511.“Fe-Catalyzed dicarbofunctionalization of electron-rich alkenes with Grignard reagents and (fluoro)alkyl halides.” Part of the 2021 Emerging Investigators Issue. Berger, K. J.; Driscoll, J. L.; Yuan, M.; Dherange, B. D.; Gutierrez, O.; # Levin, M. D. # J. Am. Chem. Soc. 2021, 143, 17366-17373.“Direct Deamination of Primary Amines via Isodiazene Intermediates.” Review. Yuan, M.; Gutierrez, O.# WIREsComput Mol Sci. 2021;e1573.“Mechanisms, Challenges, and Opportunities of Dual Ni/Photoredox Catalyzed C(sp2)-C(sp3) Cross-Couplings. ” Liu, C.F.; Wang, H.; Martin, R. T.; Gutierrez, O.; # Koh, M. J. # Nat. Catal. 2021, 4, 674-683.“Olefin functionalization/isomerization enables stereoselective alkene synthesis.” Thompson, R. R.; Rotella, M. E.; Zhou, X.; Fronczek, F. R.; Kumar, R.; Gutierrez, O.# Lee, S.# J. Am. Chem. Soc. 2021, 143, 9026-9039. “Impact of Ligands and Metals on the Formation of Metallacyclic Intermediates and a Non-traditional Mechanism for Group VI Alkyne Metathesis Catalysts.” DeMuth, J. C.; Song, Z.; Carpenter, S. H.; Boddie, T. E.; Radovic, A.; Baker, T. M.; Gutierrez, O.;# Neidig, M. L.# Chem. Sci. 2021, 12, 9398-9407.“Experimental and Computational Studies of the Mechanism of Iron-Catalysed C-H Activation/Functionalisation with Allyl Electrophiles.” Lipp, A.; Badir, S.; Dykstra, R.; Gutierrez, O.;# Molander, G. A.# Adv. Synth. Catal. 2021, 363, 3507-3520. “Catalyst-Free Decarbonylative Trifluoromethylthiolation Enabled by Electron Donor–Acceptor Complex Photoactivation.” Agrawal, T.; Martin, R.; Collins, S.; Wilhelm, Z.; Edwards, M. D.; Gutierrez, O.;# Sieber, J. D. # J. Org. Chem. 2021, 86, 5026-5046.“Access To Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.” Campbell, M. W.; Yuan, M.; Polites, V. C.; Gutierrez, O.;# Molander, G. A. # J. Am. Chem. Soc. 2021, 143, 3901-3910.“Photochemical C–H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization.” Guo, L.; Yuan, M.; Zhang, Y.; Wang, F.; Zhu, S.; Gutierrez, O.# Chu, L. # J. Am. Chem. Soc. 2020, 142, 20390-20399.“General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis.” Liu, L.; Lee, W.; Youshaw, C. R.; Yuan, M.; Geherty, M. B.; Zavalij, P. Y.; Gutierrez, O.# Chem. Sci. 2020, 11, 8301-8305.“Fe-catalyzed three-component dicarbofunctionalization of unactivated alkenes with alkyl halides and Grignard reagents.” Yuan, M.; Song, Z.; Badir, S. O.; Molander, G. A.; # Gutierrez, O.# J. Am. Chem. Soc. 2020, 142, 7225-7234.“On The Nature of C(sp3)-C(sp2) Bond Formation In Nickel-Catalyzed Tertiary Radical Cross-Couplings: A Case Study Mechanistic Study of Ni/Photoredox Catalytic Cross-Coupling of Alkyl Radicals and Aryl Halides.” Liu, L.; Lee, W.; Yuan, M.; Acha, C.; * Geherty, M. B.; * Williams, B. * Gutierrez, O.# Chem. Sci. 2020, 11, 3146-3151.“Intra- and Intermolecular Carbofunctionalization of Vinyl Cyclopropanes.” Rotella, M. E.; Der, R.; Hilinski, M. K.#; Gutierrez, O.# ACS. Catal. 2020, 10, 1, 897-906. “Mechanism of Iminium Salt-Catalyzed C(sp3)-H Amination: Factors Controlling Hydride Transfer versus H-Atom Abstraction.” Xiao, S.; Lee, W.; Chen, F.; Zavalij, P. Y.; Gutierrez, O.; # Davis, J. # Chem. Commun. 2020, 56, 6981-6984.“Oxidation of 8-Thioguanosine Gives Redox-Responsive Hydrogels and Reveals Intermediates in a Desulfurization Pathway.” Wang, H.; Liu, C.-F.; Song, Z.; Yuan, M.; Ho, Y. A.; Gutierrez, O.; # Koh, M. J. # ACS Catal. 2020, 10, 4451-4459.“Engaging a-Fluorocarboxylic Acids Directly in Decarboxylative C-C Bond Formation.” Xu, B.; Troian-Gautier, L.; # Dykstra, R.; Martin, R.; Gutierrez, O.# Tambar, U. K. # J. Am. Chem. Soc. 2020, 142, 6206-6215. “Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes”