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Alex Bugarin

Alex Bugarin

Assistant Professor

Office: 205 Chemistry Research Building (CRB)
Phone:817-272 9399

B.S. Universidad Autonoma de Zacatecas, Mexico, 2003
M.S. University of Texas at El Paso, 2005
Ph.D. Texas A&M University, 2011
Post Doctorate:  University of California, Santa Barbara, 2012

Research in the Bugarin group focuses on catalytic reaction development with applications in natural product synthesis. Areas of fundamental interest include: the identification of new reactivity patterns, the evolution of related catalytic processes, and the development of new synthetic strategies. Specifically, we are pursuing new chemistry using azides, nucleophilic and electrophilic catalysis via N-heterocyclic carbenes, synergistic catalysis, redox economy, and metal-catalyzed tandem processes.

Bugarin alpha-allenols synthesisBugarin catalysis

Dr. Bugarin received his BS in chemistry, pharmacy, and biology from Universidad Autónoma de Zacatecas in 2003, his MS from UTEP in 2005, and his Ph.D. from Texas A&M University in 2011. His doctoral training under the direction of Dr. Brian T. Connell focused on asymmetric catalysis, including ligand, catalyst, and reaction design. He then spent one year as a postdoctoral associate with Professor Javier Read de Alaniz at UC Santa Barbara working on the mild aerobic oxidation of hydroxylamines and hydrazines. Dr. Bugarin joined the faculty at UT Arlington in Fall 2012. His research interests are in the development of new organic and organometallic reactions, or more specifically, the efficient construction of carbon–nitrogen bonds, redox economy, synergistic catalysis, and their application in total synthesis, materials, and bioactive molecules.

Wanigasekara, M. S.; Huang, X.; Chakrabarty, J.; Bugarin, A.;* Chowdhury, S.*“Enrichment and Identification of Reactive Arginine Residues in Proteins by Bio-orthogonal Click Chemistry" ACS Omega. 2018, 3, 14229-14235. DOI: 10.1021/acsomega.8b01729

Barragan, E.; Noonikara Poyil, A.; Yang, C-H.; Wang, H.; Bugarin, A.* “Metal-Free Cross- Couplings of π−Conjugated Triazenes with Unactivated Arenes Via Photoactivation” Org. Chem. Front. In press DOI: 10.1039/c8qo00938d

Marichev, K. O.; Patil, S. A.; Bugarin, A.* “Recent Advances in the Synthesis, Structure Diversity, and Applications of Mesoionic 1,2,3-triazol-5-ylidene Metal Complexes” Tetrahedron 2018, 74, 2523-2546. DOI: 10.1016/j.tet.2018.04.013

Patil, V.; Patil, S. A.; Patil, R.; Bugarin, A. E.; Beaman, K.; Patil, S. A. “Exploration of (Hetero)Aryl Derivated Thienylchalcones for Antiviral and Anticancer Activities” Med. Chem. 2018, Accepted Manuscript. DOI: 10.2174/1573406414666180524074648

Patil, V.; Barragan, E.; Patil, S. A.; Patil, S.; Bugarin, A.* “A Practical Method, NaOCl- Mediated, to Prepare Thiabendazoles via Intramolecular Amination Reaction” Tetrahedron Lett. 2017, 58, 3474-3477. DOI: 10.1016/j.tetlet.2017.07.086

Barragan, E.; Bugarin, A.* “π−Conjugated Triazenes: Intermediates that Undergo Oxidations and Substitution Reactions” J. Org. Chem. 2017, 82. 1499-1506. DOI: 101.021/acs.joc.6b02705. Top 10% highest cited per year and field

Prasad, S.; C.R., S.; Huang, X.; Patil, S. A.; Bugarin, A.;* Patil, S.* “Non-Symmetrically p- Nitrobenzyl- and p-Cyanobenzyl-Substituted N-Heterocyclic Carbene-Silver(I) Complexes: Synthesis, Characterization and Antibacterial Studies” J. Coord. Chem. 2017, 70, 600-614. DOI: 10.1080/00958972.2016.1276574.

Xu, C.; Yepez, G.; Wei, Z.; Liu, F.; Bugarin, A.; Hong, Y.* "Development of Dopant-Free Conductive Bioelastomers" Nature Sci. Rep. 2016, 6, 34451. DOI: 10.1038/srep34451.

Huang, X.; Bugarin, A.* “Direct Synthesis of α-Allenols from TMS-Protected Alkynes and Aldehydes Mediated by TBAF.” Chem. Eur. J. 2016, 22, 12696-12700. DOI: 10.1002/chem. 201603250. Now, a name reaction on ReactionFlash, an app by Reaxys®.

Patil, V.; Barragan, E.; Patil, S. A.; Patil, S.: Bugarin, A.* “Direct Synthesis and Antimicrobial Evaluation of Structurally Complex Chalcones” ChemistrySelect 2016, 1, 3647-3650. DOI: 10.1002/slct.201600703.

Xu, C.; Yepez, G.; Wei, Z.; Liu, F.; Bugarin, A.; Hong, Y.* “Synthesis and Characterization of Conductive, biodegradable, Elastomeric, Polyurethanes for Biomedical Applications” J. Biomed. Mater. Res. Part A. 2016, 104, 2305-2314. DOI: 10.1002/jbm.a.3576

Patil, S.; Bugarin, A.,* “Fifty Years of π−Conjugated Triazenes” Eur. J. Org. Chem. 2016, 860- 870. DOI: 10.1002/ejoc.201501218. Top 10% highest cited

Huang, X.; Fulton, B.; White, K.; Bugarin, A.* “Metal-Free, Regio- and Stereoselective Synthesis of Linear (E)-Allylic Compounds using C, N, O, and S Nucleophiles” Org. Lett. 2015, 17, 2594-2597. Highlighted on the Organic Chemistry Portal.

Bugarin, A.; Connell, B. T.* “Z-Selective, Mg-Mediated Synthesis of α,β-Unsaturated-β-Iodo Morita-Baylis-Hillman-type Adducts” Tetrahedron Lett. 2015, 56, 3285-3287

Bhawal R.P.; Sadananda S.C.; Bugarin A., Laposa B.; Chowdhury S.M. "Mass spectrometry cleavable strategy for identification and differentiation of prenylated peptides" Anal Chem. 2015 87, 2178-2186.

Patil S.; Bugarin A.; "Crystal structure of (E)-1,3-dimethyl-2-[3-(3-nitro-phen-yl)triaz-2-en-1-yl-idene]-2,3-di-hydro-1H-imidazole" Acta Crystallogr Sect E Struct Rep Online. 2014 70(Pt 10):224-7.

Yepremyan, M.; Yepremyan, A.; Bugarin, A.* "Surgical Glue: A Brief Overview" Austin J Biomed. Eng. 2014, 1,(4) 3.

Patil, S., White, K.; Bugarin, A.* "Novel Triazene Dyes from N-Heterocyclic Carbenes and Azides: Synthesis, Stability, and Spectroscopic Properties" Tetrahedron Lett. 2014, 55, 4826-4829.

Bugarin, A.* Martinez, L. E. Cooke, P. Islam, T. & Noveron, J. C. "Solid-phase organic synthesis of 2-tridecanyl-1,4-naphthoquinone and 2-tridecanyl-1,4-naphthodiol that form redox-active micelles and vesicles". Bioorg. Chem. 2014, 56, 62-66.

Sandoval, D.; Frazier, C, P.; Bugarin, A.; Read de Alaniz, J. "Electrophilic α-Amination Reaction of -Ketoesters Using N-Hydroxycarbamates: Merging Aerobic Oxidation and Lewis Acid Catalysis" J. Am. Chem. Soc. 2012, 134, 18948-18951.

Frazier, C, P.; Bugarin, A.; Engelking, J. R.; Read de Alaniz, J. "Copper-Catalyzed Aerobic Oxidation of N-Substituted Hydroxylamines: Efficient and Practical Access to Nitroso Compounds" Org. Lett. 2012, 14, 3620-3623.

Bugarin, A.; Connell, B. T. "A Highly Active and Selective Palladium(II) PheBox Catalyst for the Formation of α-Aryl Ketones via Cross-Coupling" Chem. Comm. 2011, 47, 7218-7220. (Highlightedas a cutting-edge contribution).

Bugarin, A.; Connell, B. T. "MgI2-Accelerated Enantioselective Morita Baylis–Hillman Reactions of Cyclopentenone Utilizing a Chiral DMAP Nucleophile"Chem. Comm. 2010, 46, 2644-2646. (Highlighted on Synfacts, 2010, 7, 788 and on the Organic Chemistry Portal).

Buddhadeb, G.; Bugarin, A.; Connell B.T.; North, S. W. "OH radical Initiated Oxidation of 1,3-Butadiene: Isomeric Selective Study of the Dominant Addition Channel" J. Phys. Chem. A. 2010, 114, 5299-5305.

Bugarin, A.; Jones K. D.; Connell, B. T. "Efficient, Direct α-Methylenation of Carbonyls Mediated by Diisopropylammonium Trifluoroacetate" Chem. Comm. 2010, 46, 1715-1717.

Buddhadeb, G.; Bugarin, A.; Connell B.T.; North, S. W. "OH Initiated Oxidation of Isoprene: Isomeric Selective Study for the Dominant Addition Channel" J. Phys. Chem. A. 2010, 114, 2553-2560.

Bugarin, A.; Connell, B. T. "Acceleration of the Morita-Baylis-Hillman Reaction by a Simple Mixed Catalyst System" J. Org. Chem. 2009, 74, 4638-4641.Highlighted on the Organic Chemistry Portal.

Bugarin, A.; Connell, B. T. "Chiral Nickel(II) and Palladium(II) NCN-Pincer Complexes Based on Substituted Benzene: Synthesis, Structure, and Lewis Acidity" Organometallics 2008,27, 4357-4369.

Yong, J. K.; Bugarin, A.; Connell, B. T. Hot Article: "Conversion of Nitrosobenzenes to isoxazolidines: An Efficient Cascade Process Utilizing Reactive Nitrone Intermediates" Chem. Comm. 2008, 44, 3522-3524.

2008 - 2011   SACNAS conference and membership waiver, presented by SACNAS. 2010

2011               Outstanding tutor award, Presented by TAMU-SACNAS chapter.

April 2011      U.S. Senator Phil Gramm Doctoral Fellowship.

Feb. 2011      Thomas J. Hairston Memorial Graduate Scholarship.

Summer 2010 Department of Bioorganic Chemistry, Life Technologies, Austin, TX

May 2010       Marie and Jim Galloway Graduate Scholarship.

May 2010       Best total synthesis proposal award, presented by Texas A&M.

Oct. 2009       The DuPont Award for general and organic chemistry to graduate oral symposia.

May 2007       Best total synthesis proposal award, presented by Texas A&M.

Nov. 2006      Outstanding Graduate Student in Chemistry, presented by UTEP.

April 2005      Outstanding Master of Chemistry in Research, presented by UTEP.

Dec - 2002     National Institute of Nuclear Research, ININ, Estado de Mexico, MX

2001-2003     Regional Center of Nuclear Studies, UAZ, Zacatecas, MX

May 2000       Placed first for the State Delegation in the National Chemistry Olympics.

May 1997       Placed first in the 11th National Mathematics Olympics, MX.

May 1997       Placed first at the Physics state championship, presented by CBTa (Mexico).