Independent Research

33. Rotella, M. E.; Sar, D.; Liu, L.; Gutierrez, O.# 

Chem. Commun. 2021, in press.

“Fe-Catalyzed dicarbofunctionalization of electron-rich alkenes with Grignard reagents and (fluoro)alkyl halides.” Part of the 2021 Emerging Investigators Issue.

Link to paper

32. Liu, L.; Aguilera, M. C.; Lee, W.; Youshaw, C. R.; Neidig, M. L.;#  Gutierrez, O.# 

Science 2021374, 432-439.

“General method for iron-catalyzed multicomponent radical cascades-cross-couplings.” 

Free-Access Link to the Paper

  • Highlighted in Science by Guillaume Lefèvre: LINK

  • Featured  in Texas A&M Science by Shana K. Hutchins "Texas A&M Chemist Helps Pave Way for Cheaper, Faster, Safer Chemical Synthesis Using Iron as Catalyst"  LINK

  • This work was highlighted by the University of Rochester "A big leap forward in using iron catalysts for pharmaceuticals"  LINK

 

31. Wang, H.; Liu, C.F.; Martin, R. T.; Gutierrez, O.; #  Koh, M. J. # 

Submitted

“Directing Group-Free Alkene Dicarbofunctionalization.” 

 

30. Berger, K. J.; Driscoll, J. L.; Yuan, M.; Dherange, B. D.;  Gutierrez, O.; #  Levin, M. D. # 

J. Am. Chem. Soc. 2021, in press. doi.org/10.1021/jacs.1c09779 

“Direct Deamination of Primary Amines via Isodiazene Intermediates.”

Link to paper

29.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. ”

(Invited Article)

Link to paper

28. Liu, C.F.; Wang, H.; Martin, R. T.; Gutierrez, O.; #  Koh, M. J. # 

Nat. Catal. 20214, 674-683.

“A General Olefin Functionalization/Isomerization Strategy for Stereoselective Alkene Synthesis.” 

Link to paper

 

27. 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.”

Link to paper

 

26. 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.”

Link to paper

 

25. 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.”

Link to paper

 

  • Highlighted with VIP (Very Important Publication) designation

 

24.  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.”

Link to paper

23.  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.”

Link to paper

 

22.  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.”

Link to paper

21.  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 Grignard Reagents.”

Link to paper

  • Featured in Org. Chem by Douglass F. Taber under Highlights: Reactions of Alkenes LINK

  • Highlighted in Organic Chemistry Portal by Reto Muellerl! LINK   

  • Highlighted in SYNFACTS by Mark Lautens: LINK

 

20.  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.”

Link to paper

19.  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.”

Link to paper

  • Highlighted in SYNFACTS: LINK

 

18.  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.”

Link to paper

17. 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.”  

Link to paper

16. 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.” 

Link to paper

 

  • Highlighted in Chemistry World:LINK

     

15.  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”

Link to paper

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

Organometallics 2019, 38, 4054-4059.

“Siloxide Podand Ligand as a Scaffold for Molybdenum Catalyzed Alkyne Metathesis and Isolation of a Dynamic Metallatetrahedrane Intermediate.”

Link to paper

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

ACS Catal. 2019, 9, 8835-8842.

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

Link to paper

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

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.”

Link to paper

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

Chem 2019, 5, 2388-2404.

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

Link to paper

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

Tetrahedron 2019, 75, 129-136.

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

Link to paper

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

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

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

Link to paper

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

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

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

Link to paper

7. Review. Liu, L; Lee, W; Yuan, M.; Gutierrez, O.#

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?”

Link to paper

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

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

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

Link to paper

  • Highlighted in SYNFACTS by Paul Knochel and Juri Skotnitzki! LINK   

  • Highlighted as Top 10% most downloaded paper in a year!

 

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

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

“Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover.”

Link to paper

  •  Highlighted as 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   

 

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

Chem. Sci. 2018, 9, 3186-3191.

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

Link to paper

3. Lee, W.; Zhou, J.; Gutierrez, O.; #

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

“Mechanism of Nakamura’s Iron-Catalyzed Asymmetric Cross-coupling Reaction: The Role of Spin in Controlling Selectivity.”

Link to paper

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

Magn. Reson. Chem. 2017, 55, 210-213.

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

Link to paper

 

1. Mazzola, E. P.; # Gutierrez, O. #; Fraenkel, G. A.; Chow, A.; Doyle, M. P.; Mandler, M.; Dykstra, R.; Garg, D.; Ridge, C. D.

Concepts in Mag. Res. 2016, 45A:e21424.

“Unusually Large Scalar Coupling Between Geminal Protons in a Saturated Pyrimidine.”

Link to paper

Mentored Research

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

Org. Lett. 2018, 20, 6539-6543. 

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

 

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

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

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

 

25. Li, M.; Gutierrez, O.; Berritt, S.; Pascual-Escudero, A.; Yeşilçimen. A.; Tang, X.; Adrio, J.; Huang, G.; Nakamaru-Ogiso, E.; Kozlowski, M. C.; Walsh, J. P.

Nat. Chem. 2017. 9, 997-1004.

“Transition-Metal-Free Chemo- and Regioselective Vinylation of Azaallyls.”

 

24. 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.

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.”

 

23. 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. 

Chem. Sci. 2016, 7, 5581-5586.

“Nickel-catalyzed C-3 direct arylation of pyridinium ions for the synthesis of 1-azafluorenes.”

 

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

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

“Dynamically Complex Enzyme-Catalyzed [6+4] and [4+2].”

 

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

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

“Mechanism of R2(II)-Catalyzed Indole Formation—The Catalyst Does Not Control Product Selectivity.”

 

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

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

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

 

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

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.”

 

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

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

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

 

17. Raffier, L.; Gutierrez, O.; Stanton, G. R.; Kozlowski, M. C.; Walsh, P. J. Organometallics, 2014, 33, 5371-5377.

“Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones.”

 

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

 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.”

 

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

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

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

 

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

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

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

 

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

Chem. Sci. 2013, 4, 3997-4003.

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

 

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

 

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

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

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

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

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

“Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the Protodepalladation Steps.”

 

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

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.”

 

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

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

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

 

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

 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."

 

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

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."

 

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

Nat. Chem. 2012, 4, 405-409.

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

 

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

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.”

 

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

Organometallics. 2010, 29, 3541-3545.

“Transition Metal Intervention for a Classic Reaction - Assessing the Feasibility of Ni(0)- promoted [1,3] Sigmatropic Shifts of Bicyclo[3.2.0]hept-2-enes.”

 

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

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.”

 

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

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

 “Nature of Intermediates in Organo-SOMO Catalysis of α-Arylation of Aldehydes.”

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

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

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