Hoye, Thomas R - University of Minnesota Twin Cities

个人简介

B.S. Bucknell University, 1972 M.S. Bucknell University, 1972 (Harold W. Heine) Ph.D. Harvard University, 1976 (Robert B. Woodward)

研究领域

Synthetic and structural organic chemistry lie at the heart of most of the projects being studied in my laboratory. These include problems in mechanistic organic chemistry, natural product synthesis, synthetic applications of organometallic chemistry, sustainable polymer synthesis, and many applications of NMR spectroscopy. Collaborative projects are actively being pursued in the areas of natural product isolation and structure determination, nanoparticle block-copolymer development for drug delivery, polymer property studies, and new prodrug strategies. Honors and Awards Alfred P. Sloan Foundation Research Fellowship, 1985 Award for Outstanding Contributions to Post-baccalaureate, Graduate and Professional Education, 1999 Academy of Distinguished Teachers, University of Minnesota, 1999 Merck Professor of Chemistry, University of Minnesota, 2002-2007 Morse-Alumni Award for Excellence in Undergraduate Teaching, University of Minnesota, 2007 Merck Professor of Chemistry, University of Minnesota, 2009-2014 Minnesota Award for Outstanding Contributions to the Chemical Sciences, ACS Minnesota Section, 2014 Ernest Guenther Award in the Chemistry of Natural Products, American Chemical Society, 2015 Royal Society of Chemistry Robert Robinson Award, 2016 American Chemical Society Arthur C. Cope Scholar Award, 2017 College of Science and Engineering Distinguished Professor, 2017

近期论文

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Cycloadditions of Benzynes with the Azoxy [RN=N+(O–)R′] 1,3-Dipole Tautomer of 1-Hydroxybenzotriazole (HOBT) Lee, S.; Hoye, T. R. Org. Lett. 2024, 26, 5713–5718. Free carbenes from complementarily paired alkynes Xu, Q.; Hoye, T.R. Nature Chem. 2024, 16, 1083–1092. Cascade reactions of HDDA-benzynes with tethered cyclohexadienones: strain-driven events originating from ortho-annulated benzocyclobutenes Chinta, B. S.; Sneddon, D. S.; Hoye, T. R. Chem. Sci. 2024, 15, 8181–8189. 2:1 Adducts Arising from Reactions between Benzynes and 1,3,4-Oxadiazoles Guzman, A. L.; Kevorkian, P. V.; Hoye, T. R. Org. Lett. 2024, 26, 3834–3839. Deciphering molecular structures: NMR spectroscopy and quantum mechanical insights of halogenated 4H‐Chromenediones Martins, L. M. O. S.; Souto, F. T.; Hoye, T. R.; Alvarenga, E. S. Magn. Reson. Chem. 2024, 62, 583–598. A Cascade of Strain-Driven Events Converting Benzynes to Alkynylbenzocyclobutenes to 1,3-Dien-5-ynes to Cyclic Allenes to Benzocyclohexadienones Xu, Q.; Hoye, T. R. J. Am. Chem. Soc. 2024, 146, 6438–6443. Phosphorane-Promoted C–C Coupling during Aryne Annulations Kevorkian, P.V.; Sneddon, D.S.; Ritts, C.B.; Hoye, T.R. Angew. Chem. Int. Ed. 2024, e202318774. Novel Conversions of a Multifunctional, Bio-sourced Lactone Carboxylic Acid Kaicharla, T.; Lee, S.; Wang, R.; Pehere, A. D.; Xu, S.; Hoye, T. R. Arkivoc 2024, 202312081. Intramolecular Cyclization of Alkynylheteroaromatic Substrates Bearing a Tethered Cyano Group: A Strategy for Accessing Fused Pyridoheterocycles Kraemer, N.; Eason, E. M.; Hoye, T. R. J. Org. Chem. 2023, 88, 12716–12726. Covalent Adduct Formation between β-Lactoglobulin and Flavor Compounds under Thermal Treatments That Mimic Food Pasteurization or Sterilization Yuan, J.; Anantharamkrishnan, V.; Hoye, T. R.; Reineccius, G. A. J. Agric. Food Chem. 2023, 71, 9481–9489. The contrasting reactivity of trans- vs. cis-azobenzenes (ArN=NAr) with benzynes Sneddon, D. S.; Hoye, T. R. Chem. Sci. 2023, 14, 6730–6737. A Distinct Mode of Strain-Driven Cyclic Allene Reactivity: Group Migration to the Central Allene Carbon Atom Xu, Q.; Hoye, T. R. J. Am. Chem. Soc. 2023, 145, 9867–9875. Neighboring Group Effects on the Rates of Cleavage of Si–O–Si-Containing Compounds Gormong, E. A.; Sneddon, D. S.; Reineke, T. M.; Hoye, T. R. J. Org. Chem. 2023, 88, 1988–1995. The Dual Therapeutic Potential of Ottelione A on Carbon Tetrachloride-induced Hepatic Toxicity in Mice Zahran, R. F.; EL-sayed, L. M.; Hoye, T. R.; Ayyad, S-E. N. Appl. Biochem. Biotechnol. 2023, 195, 5966–5979. Lactone Ring-Opening Equilibria in Methanol by 1H NMR Analysis: An Assessment of the Ring-Opening Polymerizability of Lactone Monomers Jin, M.; Hoye, T. R. Macromolecules 2023, 56, 1122–1129. Electronic Character of α,3-Dehydrotoluene Intermediates Generated from Isolable Allenyne-Containing Substrates Xu, Q.; Hoye, T.R. Angew. Chem. Int. Ed. 2022, 61, e202207510. Quaternary Ammonium Ion-Tethered (Ambient-Temperature) HDDA Reactions Zhu, C.; Hoye, T.R. J. Am. Chem. Soc. 2022, 144, 7750–7757. Examples Showing the Utility of Doping Experiments in 1H NMR Analysis of Mixtures Kaicharla, T.; Chinta, B.S.; Hoye, T.R. J. Org. Chem. 2022, 87, 5660–5667. In Situ Allene Formation via Alkyne Tautomerization to Promote [4 + 2]-Cycloadditions with a Pendant Alkyne or Nitrile Kraemer, N.; Naredla, R.R.; Hoye, T.R. Org. Lett. 2022, 24, 2327–2331. Defining the Macromolecules of Tomorrow through Synergistic Sustainable Polymer Research Haque, F.M.; Ishibashi, J.S.A.; Lidston, C.A.L.; Shao, H.; Bates, F.S.; Chang, A.B.; Coates, G.W.; Cramer, C.J.; Dauenhauer, P.J.; Dichtel, W.R.; Ellison, C.J.; Gormong, E.A.; Hamachi, L.S.; Hoye, T.R.; Jin, M.; Kalow, J.A.; Kim, H.J.; Kumar, G.; LaSalle, C.J.; Liffland, S.; Lipinski, B.M.; Pang, Y.; Parveen, R.; Peng, X.; Popowski, Y.; Prebihalo, E.A.; Reddi, Y.; Reineke, T.M.; Sheppard, D.T.; Swartz, J.L.; Tolman, W.B.; Vlaisavljevich, B.; Wissinger, J.; Xu, S.; Hillmyer, M.A. Chem. Rev. 2022, 122, 6322–6373. TMS is Superior to Residual CHCl3 for Use as the Internal Reference for Routine 1H NMR Spectra Recorded in CDCl3 Guzman, A.L.; Hoye, T.R. J. Org. Chem. 2022, 87, 905–909. Trapping Reactions of Benzynes Initiated by Intramolecular Nucleophilic Addition of a Carbonyl Oxygen to the Electrophilic Aryne Chinta, B.S.; Arora, S.; Hoye, T.R. Org. Lett. 2022, 24, 425–429. Hydrothermal catalysis of waste greases into green gasoline, jet, and diesel biofuels in continuous flow supercritical water Fedie, R.L.; McNeff, C.V.; McNeff, C.V.; McNeff, L.C.; Greuel, P.G.; Yan, B.; Jenkins, J.A.; Brethorst, J.T.; Frost, G.B.; Hoye, T.R. Biofuels, Bioprod. Bioref. 2022, 16, 349–369. Synthesis of a novel naphthalenone endoperoxide and structural elucidation by NMR spectroscopy and theoretical calculation Martins, L.M.O.S.; Santos, J.O.; Hoye, T.R.; Alvarenga, E.S. Magn. Reson. Chem. 2022, 60, 139–147. Silicon as a powerful control element in HDDA chemistry: redirection of innate cyclization preferences, functionalizable tethers, and formal bimolecular HDDA reactions Lynn, M.; Smela, M.P.; Hoye, T.R. Chem. Sci. 2021, 12, 13902–13908. De novo Assembly of the Benzenoid Ring as a Core Strategy for Synthesis of the Isoindolinone Natural Products Isohericerin, Erinacerin A, and Sterenin A. Zhu, C.; Zhang, J.; Hoye, T.R. Org. Lett. 2021, 23, 7550–7554. Radial hexadehydro-Diels-Alder reactions Lee, D.; Ross, S.P.; Xiao, X.; Hoye, T.R. Chem. 2021, 7, 2527–2537. Sulfurane [S(IV)]-Mediated Fusion of Benzynes Leads to Helical Dibenzofurans Ritts, C.B.; Hoye, T.R. J. Am. Chem. Soc. 2021, 143, 13501–13506. Synthesis of Isohexide Diyne Polymers and Hydrogenation to Their Saturated Polyethers Gormong, E.A.; Reineke, T.M.; Hoye, T.R. ACS Macro Lett. 2021, 10, 1068–1072. Cu(I)-Catalyzed 1,2-Alkynyl-propargylation and -benzylation of Benzyne Derivatives Wang, Q.; Hoye, T.R. Org. Lett. 2021, 23, 5448–5451. Hexadehydro Diels–Alder (HDDA) Route to Arynes and Related Chemistry Voss, R.N.; Hoye, T.R. Hexadehydro Diels–Alder (HDDA) Route to Arynes and Related Chemistry. In Modern Aryne Chemistry; Biju, A.T.; Wiley-VCH: Weinheim, Germany, 2021; Chapter 10; pp 407–444. “Kobayashi Benzynes” as Hexadehydro-Diels–Alder Diynophiles Arora, S.; Hoye, T.R. Org. Lett. 2021, 23, 3349–3353. Arylhydrazine Trapping of Benzynes: Mechanistic Insights and a Route to Azoarenes Sneddon, S.D.; Hoye, T.R. Org. Lett. 2021, 23, 3432–3436. Coumarin (5,6-Benzo-2-pyrone) Trapping of an HDDA-Benzyne Chinta, B. S.; Lee, D.; Hoye, T. R. Org. Lett. 2021, 23, 2189–2193. β-Methyl-δ-valerolactone-containing thermoplastic poly(ester-amide)s: synthesis, mechanical properties, and degradation behavior Guptill, D. M.; Chinta, B. S.; Kaicharla, T.; Xu, S.; Hoye, T. R. Polym. Chem. 2021, 12, 1310–1316. Hexadehydro-Diels–Alder Reaction: Benzyne Generation via Cycloisomerization of Tethered Triynes Fluegel, L. L.; Hoye, T. R. Chem. Rev. 2021, 121, 2413–2444. Characterization of stereoisomeric 5‐(2‐nitro‐1‐phenylethyl)furan‐2(5H )‐ones by computation of 1H and 13C NMR chemical shifts and electronic circular dichroism spectra Lopes, D. T.; Hoye, T. R.; Alvarenga, E. S. Magn. Reson. Chem. 2021, 59, 43–51. Poly(4-ketovalerolactone) from Levulinic Acid: Synthesis and Hydrolytic Degradation Xu, S.; Wang, Y.; Hoye, T. R. Macromolecules 2020, 53, 4952–4959. Covalent Adduct Formation Between Flavor Compounds of Various Functional Group Classes and the Model Protein β-Lactoglobulin Anantharamkrishnan, V.; Hoye, T. R.; Reineccius, G. A. J. Agric. Food Chem. 2020, 68, 6395–6402. 4-Carboalkoxylated Polyvalerolactones from Malic Acid: Tough and Degradable Polyesters Fahnhorst, G. W.; De Hoe, G. X.; Hillmyer, M. A.; Hoye, T. R. Macromolecules 2020, 53, 3194–3201. Reactions of HDDA Benzynes with C,N-Diarylimines (ArCH=NAr′) Arora, S.; Sneddon, D. S.; Hoye, T. R. Eur. J. Org. Chem. 2020, 2379–2383. Addendum: A guide to small-molecule structure assignment through computation of (¹H and ¹³C) NMR chemical shifts Willoughby, P.H.; Jansma, M.J.; Hoye, T.R. Nat. Protoc. 2020, 15, 2777. The aza-hexadehydro-Diels-Alder (aza-HDDA) reaction Thompson, S. K.; Hoye, T. R. J. Am. Chem. Soc. 2019, 141, 19575–19580. Reactions of thermally generated benzynes with six-membered N–heteroaromatics: Pathway and product diversity Arora, S.; Zhang, J.; Pogula, V.; Hoye, T. R. Chem. Sci. 2019, 10, 9069–9076. Hydrolytically-degradable homo- and copolymers of a strained exocyclic hemiacetal ester Neitzel, A. E.; Barreda, L.; Trotta, J. T.; Fahnhorst, G. W.; Haversang, T. J.; Hoye, T. R.; Fors, B. P.; Hillmyer, M. A. Polym. Chem. 2019, 10, 4573–4583. One-Pot, Three-Aryne Cascade Strategy for Naphthalene Formation from 1,3-Diynes and 1,2-Benzdiyne Equivalents Xiao, X.; Hoye, T. R. J. Am. Chem. Soc. 2019, 141, 9813–9818. Divergent Reactivity during the Trapping of Benzynes by Glycidol Analogs: Ring Cleavage via Pinacol-Like Rearrangements vs Oxirane Fragmentations Zhang, J.; Hoye, T. R. Org. Lett. 2019, 21, 2615–2619. Superabsorbent Poly(isoprenecarboxylate) Hydrogels from Glucose Fahnhorst, G. W.; Hoye, T. R. ACS Sustainable Chem. Eng. 2019, 7, 7491–7495. Benzyne Cascade Reactions via Benzoxetenonium Ions and Their Rearrangements to o-Quinone Methides Shen, H.; Xiao, X.; Hoye, T. R. Org. Lett. 2019, 21, 1672–1675.