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Chemistry

College of the Sciences

Timothy Beng

 

 

Timothy Beng

Associate Professor, Organic Chemistry

Phone: (509) 963-1126
Email: timothyb@cwu.edu
Office: Science Building 302E

CWU Courses

Organic Chemistry Lecture
Organic Chemistry Lab
Current Topics in Chemistry-Chemistry of Heterocycles

Education

o    2011 – PhD University of Arkansas

o    2004 - MS, East Tennessee State University

o    2001 - BS, University of Buea

Research Interests

Development of Synthetic Methodology for Efficient and Expedient Functionalization of Nitrogen and Oxygen-Containing Heterocycles for Eventual Application in Natural and Unnatural Product Synthesis

Publications: 

  • Abdikani Omar Farah, Muhannad Rabah, and Timothy K. Beng; “Transition metal-free domino acyl substitution/Michael addition of alkenyl Grignard reagents to lactam esters: Synthesis of lactam-bearing homoallylic ketones”, RSC Advances, 2020, 10, 22454 - 22459.
  • Timothy K. Beng, Victoria Shearer, Rachel Davey, and Ivianne Redman; “Site-selective, catalytic, and diastereoselective sp3 C–H hydroxylation and alkoxylation of vicinally functionalized lactams”, RSC Advances, 2020, 10, 20264 - 20271.
  • Timothy K. Beng and Abdikani Omar Farah; “Modular access to formamide-tethered α-halo ynones via the deconstructive oxo-halogenation of readily available α-alkynyl eneformamides”, Tetrahedron Lett., 2020, 61, 151821.
  • Timothy K. Beng and Antonio Moreno; “Copper-catalyzed alkenylation of novel N-iodoarylated allylic ketopiperazinonates with unactivated alkenes”, New Journal of Chemistry, 2020, 44, 4257 - 4261.
  • Timothy K. Beng and Antonio Moreno; “Catalytic, selective, and stereocontrolled construction of C4 quaternary and homobenzylic dihydroisoquinolones by sp3 C–H benzylation”, RSC Advances, 2020, 10, 8805 - 8809.
  • Antonio Moreno and Timothy K. Beng; “Direct access to vicinally functionalized and N-trifluoroacetylated (bicyclic) ketopiperazines using a readily affordable N-heterocyclic anhydride”, Organic and Biomolecular Chemistry, 2020, 18, 1577.
  • Timothy K. Beng, Spencer Langevin, Abdikani Omar Farah, Joshua Goodsell, and Katie Wyatt; “One shot access to isoquinolone and (hetero)izidinone architectures using cyclic α-chloroeneformamides and cyclic anhydrides”, New Journal of Chemistry. 2019, 43, 5282 - 5286.
  • Timothy K. Beng and Francine Wanjiku; “Iridium-catalyzed α-alkynylation of cyclic nonaromatic eneformamides: Application to the synthesis of azapolycyclic architectures”, New Journal of Chemistry, 2019, 43, 4664 - 4668.
  • Timothy K. Beng, Megan Bauder, Morgan J. Rodriguez, and Antonio Moreno; “Copper-catalyzed regioselective dehydrogenative alkoxylation of morpholinonyl alkenols: application to the synthesis of spirotricyclic dihydropyrans and of trans-fused bicyclic morpholines”, New Journal of Chemistry. 2018, 42, 16451, DOI: 10.1039/C8NJ03890B.
  • Abdikani Omar Farah, Ryan Archibald, Morgan J. Rodriguez, Antonio Moreno, Blaise Dondji, and Timothy K. Beng; “Flexible access to 2,3,5,6-tetrasubstituted dehydropiperidines by Ni- or Co-catalyzed site-selective cross-coupling using Vilsmeier-Haack-derived α-chloro-β-formyltetrahydropyridines”, Tetrahedron Lett. 2018, 59, 3495.
  • Katie Hovenkotter, Hannah Braunstein, Spencer Langevin and Timothy K. Beng; “Expedient and modular access to 2-azabicyclic architectures by iron-catalyzed dehydrative coupling of alcohol-bearing allylic lactams”, Organic and Biomolecular Chemistry, 2017, 15, 1217
  • Hannah Braunstein, Spencer Langevin, Monique Khim, Jonathan Adamson, Katie Hovenkotter, Lindsey Kotlarz, Brandon Mansker and Timothy K. Beng; “Modular access to vicinally functionalized allylic (thio)morpholinonates and piperidinonates by substrate-controlled annulation of 1,3-azadienes with hexacyclic anhydrides”, Organic and Biomolecular Chemistry, 2016, 14; 8864
  • Timothy K. Beng, Spencer Langevin, Hannah Braunstein, and Monique Khim; “Regiocontrolled synthesis of (hetero)aryl and alkenyl dehydropyrrolidines, dehydropiperidines and azepenes by Ru-catalyzed, heteroatom-directed α-C-H activation/cross-coupling of cyclic enamides with boronic acids”, Organic and Biomolecular Chemistry, 2016, 14; 830
  • Timothy K. Beng, Nathan Fox, Daniel P. Bassler, Amir Alwali, Kayla Sincavage, and Ann Wen V. Silaire; “Trapping of carbolithiation-derived tertiary benzylic α-lithio piperidines with carbon electrophiles: Controlling the formation of α-amino quaternary and vicinal stereocenters”, Organic and Biomolecular Chemistry, 2015, 13, 8647
  • Timothy K. Beng, Ann Wen V. Silaire, Amir Alwali, and Daniel P. Bassler; “One-shot access to α,β-difunctionalized azepenes and dehydropiperidines by reductive cross-coupling of α-selenonyl-β-selenyl enamides with organic bromides”, Organic and Biomolecular Chemistry, 2015, 13, 7915
  • Timothy K. Beng, Kayla Sincavage, Ann Wen V. Silaire, Amir Alwali, Daniel P. Bassler, Laura Spence, and Oliver Beale; “Direct access to functionalized benzotropones, azepanes and piperidines by reductive cross-coupling of α-bromo enones with α-bromo enamides”, Organic and Biomolecular Chemistry, 2015, 13, 5349
  • Daniel P. Bassler, Amir Alwali, Laura Spence, Oliver Beale, and Timothy K. Beng; “Cobalt-Catalyzed Arylation and Alkenylation of Alpha-Bromo Eneformamides and Enecarbamates by Cross-Coupling with Organic Bromides: Application to the Synthesis of Functionalized Piperidines and Azepanes”, Journal of Organometallic Chemistry, 2015, 780, 6-12
  • Daniel P. Bassler, Laura Spence, Amir Alwali, Oliver Beale, and Timothy K. Beng; "Expedient Access to α,β-Difunctionalized Azepenes using α-Chloro Eneformamides: Application to the One-Pot Synthesis of 2-Benzazepanes", Organic and Biomolecular Chemistry, 2015, 13, 2285.
  • Timothy K. Beng and Nathan Fox, " Diastereoselective Synthesis of α,α,α’-Trisubstituted Pyrrolidines and Piperidines by Directed Sequential Lithiation/Alkylation", Tetrahedron Lett. 2015, 56, 119.
  • Timothy K. Beng and Daniel P. Bassler, "Vicinal Difunctionalization of Dehydropiperidines using α-Halo Eneformamides", Tetrahedron Lett. 2014, 55, 6662.
  • Timothy K. Beng, Hironori Takeuchi, Manuel Weber, and Richmond Sarpong; “Stereocontrolled synthesis of vicinally functionalized piperidines by nucleophilic β-addition of alkyllithiums to α-aryl substituted piperidine enecarbamates”, Chem. Commun., 2015, 61, 7653
  • Timothy K. Beng, Sidney M. Wilkerson-Hill, and Richmond Sarpong, "Direct Access to Functionalized Azepanes by Cross-Coupling with Alpha-Halo Eneformamides", Org. Lett. 2014, 16, 916. Corrigendum: Org. Lett. 2014, 16, 3170
  • Timothy K. Beng, Jin Sun Woo, and Robert E. Gawley, Synthetic Applications and Inversion Dynamics of Configurationally Stable 2-Lithio-2-aryl-Pyrrolidines and -Piperidines, J. Am. Chem. Soc. 2012, 134, 14764-14771
  • Timothy K. Beng, William S. Tyree, Trent Parker, Chicheung Su, Paul G. Williard, and Robert E. Gawley, “Dynamics of Catalytic Resolution of 2-Lithio-N-Boc-piperidine by Ligand Exchange”, J. Am. Chem. Soc. 2012, 134, 16845-16855
  • Timothy K. Beng and Robert E. Gawley, "Catalytic Dynamic Resolution Applied to the Synthesis of 2,6-Disubstituted Piperidines: Preparation of (+)-Lupetidine and (–)-Epidihydropinidine”, Heterocycles 2012, 24, 697. Highlighted in ChemInform 2012, 43, issue 21
  • Timothy K. Beng and Robert E. Gawley, "Application of Catalytic Dynamic Resolution of N-Boc-2-lithiopiperidine to the Asymmetric Synthesis of 2-Aryl and 2-Vinyl Piperidines", Org. Lett. 2011, 13, 394-397. Highlighted in Synfacts 2011, 4, 0430. Reviewed extensively in Chemical Reviews 2015, DOI: 10.1021/acs.chemrev.5b00162.
  • Timothy K. Beng and Robert E. Gawley," Highly Enantioselective Catalytic Dynamic Resolution of N-Boc-2-lithiopiperidine: Synthesis of (R)-(+)-Pipecolic acid, (S)-(–)-Coniine, (S)-(+)-Pelletierine, (+)-β-Conhydrine, (S)-(–)-Ropivacaine, and Formal Synthesis of (–)-Lasubine II and (+)-Cermizine C", J. Am. Chem. Soc. 2010, 132, 12216-12217. Highlighted in Synfacts 2010, 12, 1328. Reviewed extensively in Chemical Reviews 2015, DOI: 10.1021/acs.chemrev.5b00162
  • Iain Coldham, Daniele Leonori, Timothy K. Beng, and Robert E. Gawley, “The barrier to enantiomerization and dynamic resolution of N-Boc-2-lithiopiperidine and the effect of TMEDA”, Chem. Commun., 2009, 5239 – 5241; Corrigendum with correct enthalpy and entropy values: 2010, 9267−9268.
  • Timothy K. Beng, Taher I. Yousaf, Iain Coldham, and Robert E. Gawley, "Enantiomerization Dynamics and a Catalytic Dynamic Resolution of N-Trimethylallyl-2-lithiopyrrolidine", J. Am. Chem. Soc. 2009, 131, 6908-6909. Reviewed extensively in Chem. Eur. J. 2012, 18, 10092-10142

Selected Honors and Awards

Research Mini Grant, Committee of Faculty Scholarship, Susquehanna University       2014 – current

Research Funds, Department of Chemistry, Susquehanna University                               2014 – current

Ruth L. Kirschstein National Research Service Award (F32 Postdoctoral Fellowship) 2012 – 2014

Invited Speaker, RSC 21st Heterocyclic & Synthetic Group Symposium, Grasmere        2013

Two Golden Tusk Awards for Excellence in Teaching, University of Arkansas    2012

NIH Travel Grant, Pacifichem, Honululu, Hawaii            2010        

NSF Travel Grant, Gordon Research Conference, Salve Regina, Newport, Rhode Island     2010

University of Arkansas Travel Grant, 62nd Regional ACS Meeting, San Francisco         2010

Teaching & Research Assistantships, University of Arkansas                                              2007 – 2011

Margaret Sells Scholarship, East Tennessee State University         2003

Graduate Fellowship, East Tennessee State University                                                        2003 – 2004

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