Independent Research

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

Submitted

“Directing Group-Free Alkene Dicarbofunctionalization.” 

29.Review. Yuan, M.; Gutierrez, O.#

WIREs Computational Molecular Science. 2021, ACCEPTED.

“Mechanisms, Challenges, and Opportunities of Dual Ni/Photoredox Catalyzed C(sp2)-C(sp3) Cross-Couplings. ” (Invited Article)

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.”