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SUBMITTED 

99. Perea, M. A.; Bucci, E. M.; Lalisse, R. F.; Mukherjee, P.; Raab, T. J.; Valloli, L. K.; Bird, M. J.; Gutierrez,O.;#

Doyle, A. D.#

Submitted.

"Leveraging Cooperative Dual Ni Catalysis for Photoredox-Enabled Alkyl–Alkyl Cross-Coupling" 

Link to paper

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IN PRESS

 

98. Peng, Q.; Hwang, M. U.; Renteria-Gomez, A.; Mukherjee, P.; Young, R. M.; Qui, Y.; Wasielewski, M. R.; Gutierrez, O.; Scheidt, K. A. Science 2024, 385, 1471-1477.

“Photochemical phosphorus-enabled scaffold remodeling of carboxylic acids.”

Link to paper

97. Wu, F.-P.; Lenz, M.; Suresh, A.; Gogoi, A. R.; Typer, J. T.; Daniliuc, C. G.; Gutierrez, O.;# Glorious, F.#

Chem. Sci. 2024, 15, 15205-15211.

"Nitrogen-to-functionalized carbon atom transmutation of pyridine" 

Link to paper

96. Maity, Tapas.;* Rentería-Gómez, Á.;* Gutierrez, O.#

ACS Catal. 202414, 13049–13054

"Stereoselective Fe-catalyzed Decoupled Cross-couplings: Chiral vinyl oxazolidinones as effective radical lynchpins for diastereoselective C(sp2)-C(sp3) bond formation " 

Link to paper

95. Guerrero, M.;* Rentería-Gómez, Á.;* Das, D.; Gutierrez, O.#

Org. Lett. 202426, In Print. DOI: 10.1021/acs.orglett.4c02515.

"Fe-catalyzed Fluoroalkyl(hetero)arylation of Vinyl Azaarenes: Rapid and Modular Synthesis of Unsymmetrical 1,1-Bis(hetero)arylalkanes " 

Link to paper

94.Rentería-Gómez, Á.; Gutierrez, O.;# 

Nature 2024, 631, 30-31.

"Atom-swap chemistry speeds synthesis of compounds for drug discovery"  

Link to paper 

93. Masson-Makdissi, J.;* Lalisse, R. F.;* Gutierrez, O.;# Levin, M. D.#

J. Am. Chem. Soc. 2024, 146, 17719-17727.

"Evidence for Dearomatizing Spirocyclization and Dynamic Effects in the Quasi-Stereospecific Nitrogen Deletion of Tetrahydroisoquinolines" 

Link to paper (ChemRxiv)

92. Sun, P. B.; Pomfret, M. N.; Elardo, M. J.; Lalisse, R. F.; Suresh, A.; Rentería-Gómez, Á.; Keating, S.; Chen, C.; Hilberg, S. L.; Chakma, P.; Wu, Y.; Bell, R. C.; Rowan, S. J.; Gutierrez, O.;# Golder, M. R.#

J. Am. Chem. Soc. 2024, 146, 19229-19238.

"Molecular Ball Joints: Mechanochemical Perturbation of Bullvalene Hardy-Cope Rearrangements in Polymer Networks"  

Link to paper 

91. Targos, K.; Gogoi, A. R.; Rentería-Gómez, Á.; Kim, M. K.; Gutierrez, O.;# Wickens, Z. K.#

J. Am. Chem. Soc. 2024, 146, 13689-13696.

"Mechanism of Z-Selective Allylic Functionalization via Thianthrenium Salts" 

Link to paper (ChemRxiv)

90. Laskar, R.; Dutta, S.; Spies, J. C.; Mukherjee, P.; Rentería-Gómez, Á.; Thielemann, R. E.; Daniliuc, C.G.; Gutierrez, O.;# Glorius, F.#

J. Am. Chem. Soc. 2024, 146, 10899-10907.

“Gamma-Amino Alcohols through EnT-Enabled Brook Rearrangement”

Link to paper (PubMed)

89. Wu, D.; Martin, R. T.; Piña, J.; Kwon, J.; Crockett, M. P.; Thomas, A. A.; Gutierrez, O.; Park, N. H.; Hedrick, J. L.; Campos, L. M.#

Angew. Chem. Int. Ed. 202463, e202401281.

“Cyclopropenimine-Mediated CO 2 Activation for the Synthesis of Polyurethanes and Small-Molecule Carbonates and Carbamates”

Link to paper (PubMed)

88. Alvarez, E. M.; Ullah, M.; Stewart, G.; Lalisse, R.; Gutierrez, O.; Malapit, C. A.

J. Am. Chem. Soc. 2024, 146, 3591–3597.

"Site-selective electrochemical arene C–H amination"

Link to paper (PubMed)

87. Wu, F.-W.; Chintawar, C. C.; Lalisse, R.; Mukherjee, P.; Dutta, S.; Tyler, J.; Daniluc, C. G.; Gutierrez, O.;# Glorius, F.#

Nature Catal. 2024, 7, 242–251.

“Ring expansion of indene by photoredox-enabled functionalized carbon-atom insertion"

Link to paper

  • Highlighted in Nature Catalysis by Paolo Costa "Drug design via single-carbon atom insertion": LINK

  • Highlighted in Chem Europe "Chemists develop new approach to inserting single carbon atoms": LINK

86. Lin, L. Q.; Rentería-Gómez, A.; Martin, R.; Ong, K. Z. W.; Parris, A.; Gutierrez, O.;#Koh, M. J.#

Angew. Chem. Int. Ed. 2024, 63, e202317935

“Selective1,2-Hydroarylation(Alkenylation)ofgem-Difluoroalkenesto Access(CF2H) Motifs”

Link to paper (PubMed)

85. Wei,; S.; Smith-Jones, J.; Lalisse, R. F.; Hestenes, J. C.; Chen, D.; Danielsen, S. P. O.; Bell, R. C.; Churchill, E. M.; Munich, N. A.; Marbella, L. E.; Gutierrez, O.; Rubinstein, M.; Nelson, A.; Campos, L. M.  

Adv. Mat. 2024, e2113961. DOI. 10.1002/adma.202313961

"Light-Induced Living Polymer Networks with Adaptive Functional Properties"  

Link to paper (PubMed)

84. Chen, W.; Elumalai, P.; Mamlouk, H.; Rentería-Gómez, A.; Veeranna, Y.; Shetty, S.; Kumar, D.; Al-Rawashdeh, M.; Gupta, S. S.; Gutierrez, O.;# Zhou, H.;# Madrahimov. S. T.#  

Adv. Sci. 2024, i2309540. DOI: 10.1002/advs.202309540
Monodentate-phosphinoamine Nickel complex supported on Metal-Organic Framework for high performance ethylene dimerization

Link to paper (PubMed)

83. Mandal, H.; Ogunyemi, O.; Nicholson, J.; Orr, M. E.; Lalisse, R. F.; Rentería-Gómez, Á.; Gogoi, A. R.; Gutierrez, O.;# Michaudel, Q.; Goodson III, T.#

J. Phys. Chem. C. 2024, 128, 6, 2518–2528

“Linear and Nonlinear Optical Properties of All-cis and All-trans Poly(p-phenylene vinylene) ”

Link to paper (PubMed)

82. Youshaw, C. R.; Yang, M.-H.; Gogoi, A. R.; Rentería-Gómez, Á.; Liu, L.; Morehead, L. K.; Gutierrez, O.;#

Org. Lett. 202325, 8320-8325.

“Iron-Catalyzed Enantioselective Multicomponent Cross-Couplings of a-Boryl Radicals”

Link to paper (ChemRxiv(PubMed)

81. Sar, D.; Yin, S.;* Grygus, J.;* Rentería-Gómez, Á.;* Garcia, M.; Gutierrez, O.#

Chem. Sci. 2023, 14, 13007-13013. 

“Expanding Chemical Space of Enol Silyl Ethers: Catalytic Dicarbofunctionalization Enabled by Iron Catalysis”

Link to paper

 

80. Usman, F. O.; Gogoi, A. R.; Mixdorf, J. C.; Gutierrez, O.;# Nguyen, H. N.#

Angew. Chem. Int. Ed. 2023, 62, e202314843.

“Rhodium-Catalyzed Asymmetric Synthesis of 1,2-Disubstituted Allylic Fluorides”

Link to paper

  • Highlighted in SYNFACTS by Martin Oestreich: LINK

79. Renteria-Gomez, A.; Guerrero, M.;* Ramirez-Lopez, M.;* Gutierrez, O.#

Org. Lett. 2023, 25, 7440-7445.

“Regioselective Fluoroalkylarylation of Enamides Enabled by an Iron-Catalyzed Multicomponent Radical Cross-Coupling Stategy”

Link to paper (ChemRxiv)

 

78. Andreettta, P.; Martin, R. T.; Souliah, C.; Rentería-Gómez, Á.; Song, Z.; Khorramshashi Bayat, Y.; Ivlev, S.; Gutierrez, O.;# Casitas, A.#

Angew. Chem. Int. Ed. 202362, e202310129

“Experimental and Computational Studies on Cobalt(I)-Catalyzed Regioselective Allylic Alkylation Reactions”

Link to paper

  • Highlighted in Organic Process Research & Development (OPR&D): LINK

77. Aguilera, M. C.; Gogoi, A. R.; Lee, W.; Liu, L.; Brennessel, W.; Gutierrez, O.;# Neidig, M. L.#

ACS Catal. 202313, 8987-8996.

“Insight into Radical Initiation, Solvent Effects and Biphenyl Production in Iron-Bisphosphine Cross-Couplings”

Link to paper

76. Crockett, M. P.; Piña, J.; Gogoi, A. R.; Lalisse, R. F.; Nguyen, A. V.; Gutierrez, O.#; Thomas, A. A.#

J. Am. Chem. Soc. 2023, 145, 10743–10755.

“Breaking the tert-Butyllithium Contact Ion Pair: A Gateway to Alternate Selectivity in Lithiation Reactions”

Link to paper

75. Peng, Q.; Gogoi, A. R.; Renteria-Gomez, A.; Gutierrez, O.#; Scheidt, K. A.#

Chem 2023, 9, 1983-1993.

“Visible Light-Induced Coupling of Carboxylic Acids with Alcohols/Amines via Phosphorous Linchpin Strategy”

Link to paper

  • Highlighted in Science by Yoshihiro Ishihara and Junichiro Yamaguchi in Chem: LINK

74. Day, C. S.; Renteria-Gomez, A.; Ton, S. J.; Gogoi, A.; Gutierrez, O.;# Martin, R.#

Nat. Catal. 2023, 6, 244-253.

“Elucidating Electron Transfer Events in Polypyridine Nickel Complexes”

Link to paper

  • Highlighted in Nature Catalysis by Shengchun. Wang and Aiwen Lei: LINK

73. Zhou, M.; Tsien, J.; Dykstra, R.; Hughes, J. M.; Peters, B. K.; Merchant, R. R.; Gutierrez, O.#; Quin, T.#

Nat. Chem. 2023, 15, 550-559.

Alkyl Sulfinates as Cross-Coupling Partners: Programmable and Stereospecific Installation of C(sp3) Bioisosteres

Link to paper

72. Yang, Y.; Tsien, J.; Dykstra, R.; Chen, S.-J.; Wang, J. B.; Merchant, R. R.; Hughes, J. M. E.; Peters, B. K. Gutierrez, O.#; Quin, T.#

Nat. Chem. 2023, 16, 285–293.

Exploring Uncharted Chemical Space: Programmable Late-Stage Functionalization of Bridge-substituted BCP bis-Boronates

Link to paper

71. Matsuo, B.; Majhi, J.; Granados, A.; Sharique, M.; Martin, R. T.; Gutierrez, O.#; Molander, G. A.#

Chem. Sci. 2023, 14, 2379-2385.

“Transition metal-free photochemical C–F activation for the preparation of difluorinated-oxindole derivatives”

Link to paper

70. Zhu, J. L.; Schull, C. R.; Tam, A. T.; Renteria-Gomez, A.; Gogoi, A. R.; Gutierrez, O.#; Scheidt, K. A.#

J. Am. Chem. Soc. 2023, 145, 1535-1541.

“Photoinduced Acylations Via Azolium-Promoted Intermolecular Hydrogen Atom Transfer”

Link to paper

69. Dherange, B. D.; Yuan, M.; Kelly, C. B.;# Reiher, C. A.; Grosanu, C.; Berger, K. J.; Gutierrez, O.;# Levin, M.#

J. Am. Chem. Soc. 2023, 145, 17-24.

“Direct Deaminative Functionalization”

Link to paper

  • Highlighted in IN THE PIPELINE by Derek Lowe: LINK

  • Highlighted in Organic Process Research & Development (OPR&D): LINK

 

68. Li, X.; Yuan, M.; Chen, F.; Quing, F.-L.; Gutierrez, O.;# Chu, L.#

Chem 2023, 9, 154-169.

“Three-component enantioselective alkenylation of organophosphonates via nickel metallaphotoredox catalysis”

Link to paper

67. Tan.; G.; Paulus, F.;Renteria-Gomez, A.; Lalisse, R.F.; Daniliuc, C. G.;  Gutierrez, O.#; Glorius, F.#

J. Am. Chem. Soc. 2022, 144, 21664-21673.

Highly Selective Radical Relay 1,4-Oxyimination of Two Electronically Differentiated Olefins”

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  • Highlighted in SYNFACTS by Benjamin List: LINK

66. Dhungana, R. K.; Granados, A.; Ciccone, V.;  Martin, R. T.; Majhi, J.; Sharique, M.;  Gutierrez, O.#; Molander, G. A.#

ACS Catal. 2022, 12, 15750-15757.

“Trifunctionalization of Cinnamyl Alcohols Provides Access to Brominated a,a-Difluoro-g-Lactones via Photoinduced Radical-Polar-Radical Mechanism”

Link to paper

65. Altundas, B.; Alwedi, E.; Song, Z.; Gogoi, A. R.; Dykstra, R.; Gutierrez, O.;# Fleming, F. F.#

Nat. Commun. 2022, 13, 6444.

“Dearomatization of Aromatic Asmic Isocyanides to Complex Cyclohexadienes”

Link to paper

64. Renteria-Gomez, A.;* Lee, W.;* Yin, S.; Davis, M.; Gogoi, A. R; Gutierrez, O.#

ACS Catal. 2022, 12, 11547-11556.

“General and Practical Route to Diverse 1-(Difluoro)alkyl-3-aryl Bicyclo[1.1.1]pentanes Enabled by an Fe-Catalyzed Multicomponent Radical Cross-Coupling Reaction”

Link to paper  (ChemRxiv)

 

63. Majhi, J.; Dhungana, R. K.; Renteria-Gomez, A.; Sharique, M.; Li, Dong, W.; Gutierrez, O.#; Molander, G. A.#

J. Am. Chem. Soc. 2022, 144, 15871-15878.

“Metal-Free Photochemical Imino-Alkylation of Alkenes with Bifunctional Oxime Esters”

Link to paper

62. Wen, Y.; Renteria-Gomez, A.; Day, G. S.; Smith, M. F.; Yan, T-H.; Osman K., R.; Gutierrez, O.# Sharma, V. K.; # Ma, X.; # Zhou, H.-C.#

J. Am. Chem. Soc. 2022, 144, 11840-11850.

“Integrated Photocatalytic Reduction and Oxidation of Perfluorooctanoic Acid by Metal–Organic Frameworks: Key Insights into the Degradation Mechanisms.”

Link to paper

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

Chem. Commun. 2021, 57, 12508-12511.

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

Link to paper

 

60. 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

  • Highlighted by the National Science Foundation under NSF Research News "Low-Cost Iron Catalyst Produces Less Expensive Pharmaceutical Compounds!" LINK

  • Highlighted by the NSF as The Discovery Files episode GIVING PRESCRIPTIONS IRON! The Discovery Files radio feature is distributed nationally by the CBS Radio Network and carried by other radio stations across the country, from Los Angeles to Washington, D.C. The radio series is also distributed internationally to 177 countries by the American Forces Network.

  • 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

 

 

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

Nat. Chem. 2022, 14, 188-195.

“Directing-group-free catalytic dicarbofunctionalization of unactivated alkenes.” 

Link to paper

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

J. Am. Chem. Soc. 2021, 143, 17366-17373.

“Direct Deamination of Primary Amines via Isodiazene Intermediates.”

Link to paper

57.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

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

Nat. Catal. 20214, 674-683.

“Olefin functionalization/isomerization enables stereoselective alkene synthesis.” 

Link to paper

 

55. 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

 

54. 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

 

53. 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

 

52.  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

51.  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

 

50.  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

49.  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 alkyl halides and 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

48.  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

47.  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

 

46.  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

45. 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

44. 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

     

43.  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

42.  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

41.  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

40.  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

39.  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

38.  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

37. 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

36. 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

35. 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

34. 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!

 

33.  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   

 

32. 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

31. 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

30. 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

 

29. 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

Prior to Independent Career (UCLA, UC Davis, and UPenn)

28. 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

 

27. 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.” 

 

26. 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.”

 

25. 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.”

 

24. 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.”

 

23. 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].”

 

22. 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.”

 

21. 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.”

 

20. 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.”

 

19. 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.”

 

18. 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.”

 

17. 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.”

 

16. 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.”

 

15. 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.”

 

14. 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.”

 

13. 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.”

 

12. 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.”

11. 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.”

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