At the University of Maryland   



21. Chem. Sci. 2020, ASAP. (First appeared inChemRxiv. Preprint.

     Fe-Catalyzed Three-Component Dicarbofunctionalization of Unactivated Alkenes with Alkyl Halides and Grignard Reagents

      Liu, L.; Lee, W.; Youshaw, C. R.; Yuan, M.; Geherty, M. B.; Zavalij, P. Y.; Gutierrez, O.

20. Chem. Commun. 2020, ACCEPTED.

      Oxidation of 8-Thioguanosine Gives Redox-Responsive Hydrogels and Reveals Intermediates in a Desulfurization Pathway  

      Xiao, S.; Lee, W.; Chen, F.; Zavalij, P. Y.; Gutierrez, O.; Davis, J.  

19. ACS Catal. 2020, 10, 4451-4459.

      Engaging a-Fluorocarboxylic Acids Directly in Decarboxylative C-C Bond Formation.  

      Wang, H.; Liu, C.-F.; Song, Z.; Yuan, M.; Ho, Y. A.; Gutierrez, O.; Koh, M. J. 

  •       Highlighted in Chemistry World: LINK


18. 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.  

      Yuan, M.; Song, Z.; Badir, S. O.; Molander, G. A.; Gutierrez, O. 

  •       Top-20 most read paper in April-May: LINK

17. J. Am. Chem. Soc. 2020, 142, 6206-6215.

     Photocatalyzed Diastereoselective Isomerization Of Cinnamyl Chlorides to Cyclopropanes

      Xu, B.; Troian-Gautier, L.; Dykstra, R.; Martin, R.; Gutierrez, O.; Tambar, U. K.

16. Chem. Sci. 2020, 11, 3146. (First appeared in ChemRxiv. Preprint.

     Intra- and Intermolecular Fe-Catalyzed Dicarbofunctionalization of Vinyl Cyclopropanes

      Liu, L.; Lee, W.; Yuan, M.; Acha, C.; Geherty, M. B.; Williams, B. Gutierrez, O.

  •       Highlighted in SYNFACTS: LINK

  •       Back Inside Cover











15. ACS Catal. 2020, 10, 897-906.

      Mechanism of Iminium Salt-Catalyzed C(sp3)-H Amination: Factors Controlling Hydride Transfer versus H-Atom Abstraction

      Rotella, M. E.; Der, R.; Hilinski, M. K.; Gutierrez, O. 

14. Organometallics 2019, 38, 4054-4059

      Siloxide Podand Ligand as a Scaffold for Molybdenum Catalyzed Alkyne Metathesis and Isolation of a Dynamic

      Metallatetrahedrane Intermediate

      Thompson, R. R.; Rotella, M. E.; Du, P.; Zhou, X.; Fronczek, F. R.; Kumar, R.; Gutierrez, O.; Lee, S. 

13. ACS Catal. 2019, 9, 8835-8842.

      Oxa- and Azabenzonorbornadienes as Electrophilic Partners under Photoredox/Nickel Dual Catalysis

      Luo.; Gutierrez-Bonet, A.; Matsui, J. K.; Rotella, M. E.; Dykstra, R.; Gutierrez, O.; Molander, G. A. 

12. J. Am. Chem. Soc. 2019, 141, 14843-14852.

      The Role of Trichloroacetimidate To Enable Iridium-Catalyzed Regio- and Enantioselective Allylic Fluorination: A Combined 

      Experimental and Computational Study

      Sorlin, A. M.; Mixdorf, J. C.; Rotella, M.; Martin, R.; Gutierrez, O.; Nguyen, H. M. 

11. Chem2019, 5, 2388-2404

      The Role of Iodanyl Radicals as Critical Chain Carriers in Aerobic Hypervalent Iodine Chemistry

      Hyun, S.-M.; Yuan, M.; Maity, A.; Gutierrez, O.; Powers, D. C.


10. Tetrahedron. 2018, 75, 129-136.

      Radical-clock α-halo-esters as mechanistic probes for bisphosphine iron-catalyzed cross-coupling reactions

      Liu, L.; Lee, W.; Zhou, J.; Bandyopadhyay, S.; Gutierrez, O.

09. Org. Biomol. Chem. 2018, 17, 1767-1772.

      Mechanism of Nitrones and Allenoates Cascade Reactions for the Synthesis of Dihydro[1,2-a]indoles

      Lee, W.; Yuan, M.; Acha. C.; Onwu, A.; Gutierrez, O.


08. Angew. Chem. Int. Ed. 2018, 57, 17146-17150.

      Templating and Catalyzing [2 + 2] Photocycloaddition in Solution Using a Dynamic G‐Quadruplex

      Sutyak, K. B.; Lee, W.; Zavalij, P. V.; Gutierrez, O.; Davis, J. T.



07. Comment. Inorg. Chem. 2018, 38, 210-237.

      Mechanisms of Bisphosphine Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions: Inner-Sphere or Outer-Sphere Arylation?

      (invited contribution)

      Liu, L; Lee, W; Yuan, M.; Gutierrez, O. 


06. Angew. Chem. Int. Ed. 2018, 57, 15847-15851.

      Photoredox/Nickel-Catalyzed Single-Electron Tsuji-Trost Reaction: Development and Mechanistic Insight

      Matsui, J.; Gutierrez-Bonet, A.; Rotella, M.; Alam, R.; Gutierrez, O.; Molander, G. A

      Highlighted in SYNFACTS by Paul Knochel and Juri Skotnitzki! LINK   

      Highlighted: Top 10% most downloaded paper in a year!


05. Org. Lett. 2018, 20 6539-6543. 

      Divergent Reactivity in Pd-Catalyzed [3,3]-Sigmatropic Rearrangement of Allyloxy- and Propargyloxyindoles Revealed by 

      Computation and Experiment

      Gutierrez, O.; Hendrick, C. E.; Kozlowski, M. C.


04. J. Am. Chem. Soc. 2018, 140, 8037-8047.

      Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover

      Phelan, J. P.; Lang, S. B.; Compton, J. S.; Kelly, C. B.; Dykstra, R.; Gutierrez, O.; Molander, G. A.

      Highlights: Featured in the top 10 "Most Read Articles" in July 2018! 

      Highlighted in SYNFACTS by Paul Knochel and Moritz Balkenhohl! LINK     

      Highlighted in Organic Chemistry Portal by Reto Muellerl! LINK   

03. Chem. Sci2018, 9, 3186-3191.

     Engaging Sulfinate Salts via Ni/Photoredox Dual Catalysis Enables Facile Csp2–SO2R Coupling

     Cabrera-Afonso, M. J.;  Lu,Z.-P.; Kelly, C. B.;  Lang, S. B.; Dykstra, R.;  Gutierrez, O.; Molander, G. A.

 02. Adv. Synth. Catal. 2018, 360, 1426-1432.

     A Simple Procedure for the Synthesis of β -Hydroxyallenamides via Homoallenylation of Aldehydes

     Kim, B.-S.; Gutierrez, O.; Kozlowski, M.; Walsh, P. J.




01. J. Am. Chem. Soc. 2017, 139, 16126-16133.  

      Mechanism of Nakamura’s Bisphosphine Iron-Catalyzed Asymmetric C(sp2)-C(sp3) Cross-Coupling Reaction: The Role of Spin in

      Controlling Arylation Pathway

      Lee, W.; Zhou, J.; Gutierrez, O


PRE-University of Maryland 


29. Org. Lett. 201719, 5064-6067.   

      A Computational Investigation of the Ligand-Controlled Cu-Catalyzed Site-Selective Propargylation and Allenylation of Carbonyl        


      Zhou, Y.; Gutierrez, O.; Sader, A. C.; Patel, N. D.; Fandrick, D. R.; Busacca, C. A.; Frandrick, K. R.; Kozlowski, M.; Senanayake, C.

      H. H. 


28. Nature Chem. 2017, 9, 997-1004.

      Transition-metal-free chemo- and regioselective vinylation of azaallyls 

      Li, M.; Gutierrez, O.; Berritt, S.;  Pascual-Escudero, A.; Yeşilçimen, A.; Yang, X.; Adrio, J.; Huang, G.; Nakamaru-Ogiso,

      E.; Kozlowski, M. C.; Walsh, P. J.

      Highlighted in Phys.Org (link:




27. J. Am. Chem. Soc. 2016, 138, 15473-15481.

      Sequential C-H Arylation and Enantioselective Hydrogenation Enables Ideal Asymmetric Entry to the Indenopiperidine Core of an  

      11β-HSD-1 Inhibitor

      Wei, X.;Qu, B.; Zeng, X.; Savoie, J.; Fandrick, K. R.; Desrosiers, J.-N.; Tcyrulnikov, S.; Marsini, M. A.; Buono, F. G.;  Li, Z.; Yang

      B.-S.; Tang, W.; Haddad, N.; Gutierrez, O.; Wang, J.; Lee, H.; Ma, S.; Campbell, S.; Lorenz, J. C.; Eckhardt, M.; Himmelsbach, F.;

      Peters, S.; Patel, N. D.; Tan, Z.; Yee, N. K.; Song, J. J.; Roschangar, F.; Kozlowski, M. C.; Senanayake, C. H.


26. Chem. Sci2016, 7, 5581-5586.

      Nickel-Catalyzed C-3 Direct Arylation of Pyridinium Ions for the Synthesis of 1-Azafluorenes

      Desrosiers, J. N.; Wei, X.; Gutierrez, O.; Savoie, J.; Qu, B.; Zeng, X.; Lee, H.; Grinberg, N.; Haddad, N.; Yee, N. K.; Roschangar, F.;                Song, J. J.; Kozlowski, M. C.; Senanayake, C. H.


25. Magn. Reson. Chem. 2016, DOI: 10.1002/mrc.4466 

      Application of a Computer-assisted Structure Elucidation Program for the Structural Determination of a New Terpenoid Aldehyde with       an Unusual Skeleton

      Li, X.-N.; Ridge, C. D.; Mazzola, E. P.; Sun, J.; Gutierrez, O.; Moser, A.; DiMartino, J. C.; MacDonald, S. A.; Chen, P. ​​


24. J. Am. Chem. Soc. 2016, 138, 3631-3634.

      Dynamically Complex [6+4] and [4+2] Cycloadditions in the Biosynthesis of Spinosyn A

      Patel, A.; Chen, Z.; Yang, Z.; Gutierrez, O.; Liu, H.-v.; Houk, K. N.; Singleton, D. A.


23. J. Am. Chem. Soc. 2016, 138, 487-490.

      Mechanism of Rh2(II)-Catalyzed Indole Formation—The Catalyst Does Not Control Product Selectivity

      Harrison, G. J.; Gutierrez, O.; Jana, N.; Driver, T.; Tantillo, D. J. 




22. J. Am. Chem. Soc. 2015, 137, 11491-11497.

      Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights

      Wanner, B.; Kreituss, I.; Gutierrez, O.; Kozlowski, M. C.; Bode, J. W.


21. J. Am. Chem. Soc. 2015, 137, 4896-4899.

      Nickel-Catalyzed Cross-Coupling of Photoredox Generated Radicals: Uncovering a General Manifold for Stereoconvergence

      in Nickel-Catalyzed Cross-Couplings

      Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.; Kozlowski, M. C.


20. Org. Lett. 2015, 17, 1742-1745.

      Development and Origin of Diastereoselectivity of a Practical and Asymmetric Route to Sitagliptin and Derivatives

      Gutierrez, O.; Dattatray, M.; Dwivedi, M.; Gudimalla, N.; Chandrashekar, E. R. R.; Vilas, D. H.; Bhattacharya, A.; Bandichhor, R.;

      Kozlowski, M. C.


19. BOOK:  Understanding Organometallic Reaction Mechanisms and Catalysis. Editor Valentin Ananikov. Wiley-VCH. Weinheim 2015.

      Computational Studies on Sigmatropic Shifts via Alkene and Alkyne Activation by Palladium and Gold

      Gutierrez, O.; Kozlowski, M. C.




18. J. Am. Chem. Soc. 2014, 136, 11783-11791.

      Concerted Amidation of Activated Esters: Reaction Path and Origins of Selectivity in the Kinetic Resolution of Cyclic Amines via   

      NHC and Hydroxamic Acid Co-Catalyzed Acyl Transfer    

      Allen, S. E.; Hsieh, S.-Y.; Gutierrez, O.; Bode, J. W.; Kozlowksi, M. C.


17. Organometallics, 2014, 33, 5371-5377 .

      Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones

      Raffier, L.; Gutierrez, O.; Stanton, G. R.; Kozlowski, M. C.; Walsh, P. J.


16. Org. Lett. 2014, 16, 468-471.

       Stereocontrol in Asymmetric SE’ Reactions of γ-Substituted α,β-Unsaturated Aldehydes

       Williams, D. R.; Atwater, B, A.; Ke, P.; Gutierrez, O.; Tantillo, D. J.




15. Angew. Chem. Int. Ed. 2013, 53, 1279-1282.

      Through-Bond/Through-Space Anion Relay Chemistry Exploiting Vinylepoxides as Bifunctional Linchpins

      Chen, M. Z.; Gutierrez, O.; Smith III, A. B.


14. Chem. Sci. 2013, 4, 3997-4003.

      Mechanism of Triflimide-Catalyzed [3,3]-Sigmatropic Rearrangements of N-Allylhydrazones – Predictions and Experimental


     Gutierrez, O.; Strick, B, F.; Thomson, R. J.; Tantillo, D. J.


13. Chem. Sci. 2013, 4, 3894-3898.

      Carbonium vs. Carbenium Ion-like Transition State Geometries for Carbocation Cyclization – How Strain Associated with

      Bridging Affects 5-exo vs. 6-endo Selectivity

      Gutierrez, O.; Harrison, J. G.; Felix, R. J.; Guzman, F. C.; Gagné, M. R.; Tantillo, D. J.


12. J. Org. Chem. 2013, 78, 5685-5690.

     Gold(I)-Catalyzed Formation of Bicyclo[4.2.0]oct-1-enes

     Felix, R. J.; Gutierrez, O.; Tantillo, D. J.; Gagné, M. R.


11. J. Org. Chem. 2013, 78, 4744-4761.

     Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the

     Protodepalladation Steps

     Dickstein, J. S.; Curto, J. M.; Gutierrez, O.; Mulrooney, C. A.; Kozlowski, M. C.




10. Nature Chem. 2012, 4, 405-409. 

      A Au-Catalyzed Enantioselective Cope Rearrangement of Achiral 1,5- Dienes

      Felix, R. J.; Weber, D.; Gutierrez, O.; Tantillo, D. J.; Gagné, M. R.


09. J. Org. Chem. 2012, 77, 8845-8850.

     Analogies Between Synthetic and Biosynthetic Reactions in which [1,2]-Alkyl Shifts are Combined with Other Events-Dyotropic,

     Schmidt and Carbocation Rearrangements

     Gutierrez, O.; Tantillo, D. J.


08. Chem. Eur. J. 2012, 18, 11029-11035.

      Reexamining the Mechanisms of Competing [3,3] and [3,5] Sigmatropic Shifts of 1,3,7-Octatriene

      Gutierrez, O.; Harrison, J. G.; Pemberton, R. P.; Tantillo, D. J.


07. J. Am. Chem. Soc. 2012, 134, 6528-6531.

     Stereocontrol in a Combined Allylic Azide Rearrangement and Intramolecular Schmidt Reaction: Application to Asymmetric

     Synthesis of Pinnaic Acid

     Liu, R.; Gutierrez, O.; Tantillo, D. J.; Aubé, J.


06. J. Mass Spectrom. 2012, 47, 676-686.

     Fragmentation of Oxime and Silyl-oxime Ether Odd-electron Positive Ions by the McLafferty Rearrangement: New Insights on

     Structural Factors that Promote α, β-Fragmentation

     Laulhe, S.; Bogdanov, B.; Johannes, L. M.; Gutierrez, O.; Harrison, J. G.; Tantillo, D. J.; Zhang, X.; Nantz, M. H.


05. J. Org. Chem. 2012, 77, 640-647.
     Mechanism of the Acid Promoted Intramolecular Schmidt Reaction. Theoretical Assessment of the Importance of Lone

     Pair-Cation, Cation-pi and Steric Effects in Controlling Regioselectivity

     Gutierrez, O.; Aubé, J.; Tantillo, D. J.




04. Organometallics 2010, 29, 3541-3545.

      Transition Metal Intervention for a Classic Reaction - Assessing the Feasibility of Ni(0)- promoted [1,3] Sigmatropic Shifts of


      Gutierrez, O.; Tantillo, D. J.


03. J. Org. Chem. 2010, 75, 6933-6940.
     Synthesis of a trans, syn, trans-Dodecahydrophenanthrene via a Bicyclic Transannular Diels-Alder Reaction: Intermediate for the

     Synthesis of Fusidic Acid

     Jung, M E.; Zhang, T.-H.; Lui, R. M.; Gutierrez, O.; Houk, K. N.


02. J. Am. Chem. Soc. 2010, 132, 6001-6005.

     Nature of Intermediates in Organo-SOMO Catalysis of α-Arylation of Aldehydes

     Um, J. M.; Gutierrez, O.; Schoenebeck, F.; Houk, K. N.; MacMillan. D. W. C.




01.Org. Lett. 2009, 11, 4298-4301.

     Origin of Stereoselectivity in the Imidazolidinone-Catalyzed Reductions of Cyclic α, β- Unsaturated Ketones

     Gutierrez, O.; Iafe, R.; Houk, K. N.


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