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Monosubstituted, Anionic Imidazolyl Ligands from N−H NHC Precursors and Their Activity in Pd‐Catalyzed Cross‐Coupling Reactions

https://doi.org/10.1002/adsc.202000483

Martinez, Erin_E; Jensen, Christopher_A; Larson, Alexandra_J_S; Kenney, Karissa_C; Clark, Kyle_J; Nazari, S_Hadi; Valdivia‐Berroeta, Gabriel_A; Smith, Stacey_J; Ess, Daniel_H; Michaelis, David_J (June 2020, Advanced Synthesis & Catalysis)

Abstract We report that treatment of several 2‐diphenylphosphinoimidazoles with Pd(II) salts generates monosubstituted N−H NHC−Pd complexes via insertion into the C−P bond. Removal of the N−H proton in situ leads to anionic (X‐type) or imidazolyl‐Pd complexes that are highly stable and catalytically active, achieving up to 340,000 turnovers at 1 ppm catalyst loading in Suzuki‐Miyaura reactions. DFT‐calculated Tolman electronic parameters for the sterically small ligands suggest that these ligands are significantly more donating than traditional NHCs, which provides a rationale for rapid cross‐coupling catalysis. Excellent reactivity is also demonstrated in Sonogashira reactions. magnified image
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Allene Trifluoroacetoxylation with a 2-Phosphinoimidazole-Derived Bimetallic Rh(II) Catalyst

https://doi.org/10.1021/acscatal.3c02994

Forson, Kelton G; Owens, Rachel N; Parkman, Jacob A; Bohman, Benjamin O; Wayment, Coriantumr Z; McKnight, Caitlyn E; Davis, Rhen C; Stillwell, Lillian R; Kini-Lopes, Kamahao; Cole, Rebecca J; et al (October 2023, ACS Catalysis)

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Experiment and Theory of Bimetallic Pd-Catalyzed α-Arylation and Annulation for Naphthalene Synthesis

https://doi.org/10.1021/acscatal.1c02731

Ence, Chloe C.; Martinez, Erin E.; Himes, Samuel R.; Nazari, S. Hadi; Moreno, Mariur Rodriguez; Matu, Manase F.; Larsen, Samantha G.; Gassaway, Kyle J.; Valdivia-Berroeta, Gabriel A.; Smith, Stacey J.; et al (August 2021, ACS Catalysis)
null (Ed.)
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Effect of Precatalyst Oxidation State in C–N Cross-Couplings with 2-Phosphinoimidazole-Derived Bimetallic Pd(I) and Pd(II) Complexes

https://doi.org/10.1021/acs.organomet.1c00315

Martinez, Erin E.; Moreno, Mariur Rodriguez; Barksdale, Caleb A.; Michaelis, David J. (August 2021, Organometallics)
null (Ed.)
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Time-Resolved Ultraviolet–Infrared Experiments Suggest Fe–Cu Dinuclear Arene Borylation Catalyst Can Be Photoactivated

https://doi.org/10.1021/acs.organomet.1c00136

Davis, Jacob T.; Martinez, Erin E.; Clark, Kyle J.; Kwon, Doo-Hyun; Talley, Michael R.; Michaelis, David J.; Ess, Daniel H.; Asplund, Matthew C. (June 2021, Organometallics)
null (Ed.)
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2-Phosphinoimidazole Ligands: N–H NHC or P–N Coordination Complexes in Palladium-Catalyzed Suzuki–Miyaura Reactions of Aryl Chlorides

https://doi.org/10.1021/acs.organomet.1c00165

Martinez, Erin E.; Larson, Alexandra J.; Fuller, Sydney K.; Petersen, Kathryn M.; Smith, Stacey J.; Michaelis, David J. (June 2021, Organometallics)
null (Ed.)
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Boron-Templated Dimerization of Allylic Alcohols To Form Protected 1,3-Diols via Acid Catalysis

https://doi.org/10.1021/acs.orglett.9b03760

Nazari, S. Hadi; Forson, Kelton G.; Martinez, Erin E.; Hansen, Nicholas J.; Gassaway, Kyle J.; Lyons, Nathan M.; Kenney, Karissa C.; Valdivia-Berroeta, Gabriel A.; Smith, Stacey J.; Michaelis, David J. (December 2019, Organic Letters)

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Synthesis of chiral titanium-containing phosphinoamide ligands for enantioselective heterobimetallic catalysis

https://doi.org/10.1016/j.tet.2019.04.063

Ence, Chloe C.; Walker, Whitney K.; Stokes, Ryjul W.; Martinez, Erin E.; Sarager, Spencer M.; Smith, Stacey J.; Michaelis, David J. (June 2019, Tetrahedron)

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C–N Bond Formation from Allylic Alcohols via Cooperative Nickel and Titanium Catalysis

https://doi.org/10.1021/acs.joc.8b01474

Nazari, S. Hadi; Tiempos-Flores, Norma; Forson, Kelton G.; Bourdeau, Jefferson E.; Michaelis, David J. (July 2018, The Journal of Organic Chemistry)

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Nickel-Catalyzed Suzuki Cross Couplings with Unprotected Allylic Alcohols Enabled by Bidentate N -Heterocyclic Carbene (NHC)/Phosphine Ligands

https://doi.org/10.1021/acscatal.7b03079

Nazari, S. Hadi; Bourdeau, Jefferson E.; Talley, Michael R.; Valdivia-Berroeta, Gabriel A.; Smith, Stacey J.; Michaelis, David J. (December 2017, ACS Catalysis)

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