innovations in bioactive small molecule synthesis

publications

C-H functionalization

We are currently investigating new catalytic strategies
for the selective modification of C–H bonds in complex molecules, to enable  precision molecular editing  
as a drug discovery strategy.

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heterocycles: methods and targets

Nitrogen-containing heterocyclic are common in pharmaceuticals and are a defining feature of alkaloid natural products. We seek to develop fundamentally new synthetic approaches with broad applicability.

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recent News

new NIH Funding

We have received a new R35 (MIRA) award from the NIH! It will support projects on new C–H functionalization and Diels-Alder reactions.

Anna at the GRC

PhD student Anna Davis was selected from among all poster presenters to give a short talk at the Organic Reactions & Processes GRC. Congrats!

Ian's fellowship

PhD student Ian Winchester has been awarded a training grant fellowship from the UVA Comprehensive Cancer Center. Congrats!

publications

Metal-Free Homogeneous O2 Reduction by an Iminium-Based Electrocatalyst

E. N. Cook, A. E. Davis, M. K. Hilinski, C. W. Machan, J. Am. Chem. Soc. 2024, 146, 7931-7935.

Amine Organocatalysis of Remote, Chemoselective C(sp3)–H Hydroxylation

P. L. Hahn, J. M. Lowe, Y. Xu, K. L. Burns, M. K. Hilinski, ACS Catal. 2022, 12, 4302-4309.

Vinylazaarenes as Dienophiles in Lewis Acid-Promoted Diels-Alder Reactions

A. E. Davis, J. M. Lowe, M. K. Hilinski, Chem. Sci. 2021, 12, 15947-15952.

1,1,1-Trifluoro-2-hexanone

S. L. Johnson and M. K. Hilinski, e-EROS Encyclopedia of Reagents for Organic Synthesis [Online], John Wiley & Sons, 2020.

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

M. E. Rotella, R. M. B. Dyer, M. K. Hilinski, and O. Gutierrez, ACS Catal., 2020, 10, 897-906.

Intermolecular Scandium Triflate-Promoted Nitrene Transfer [5+1] Cycloadditions of Vinylcyclopropanes

J. E. Laudenschlager, L. A. Combee, M. K. Hilinski, Org. Biomol. Chem. 2019, 17, 9413-9417.

Rh(II)-Catalyzed Nitrene-Transfer [5+1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes

L. A. Combee, S. L. Johnson, J. E. Laudenschlager, M. K. Hilinski, Org. Lett. 2019, 21, 2307-2311.

Organocatalytic Atom-Transfer C(sp3)-H Oxidation

S. L. Johnson, L. A. Combee, M. K. Hilinski, Synlett 2018, 29, 2331-2336.

Selective Heteroaryl N-Oxidation of Amine-Containing Molecules

R. M. B. Dyer, P. L. Hahn, M. K. Hilinski, Org. Lett. 2018, 20, 2011-2014.

Organocatalytic, Dioxirane-Mediated C–H Hydroxylation Under Mild Conditions Using Oxone

W. G. Shuler, S. L. Johnson, M. K. Hilinski, Org. Lett. 2017, 19, 4790-4793.

An Iminium Salt Organocatalyst for Selective Aliphatic C–H Hydroxylation

D. Wang, W. G. Shuler, C. J. Pierce, M. K. Hilinski, Org. Lett. 2016, 18, 3826-3829.

Intermolecular Electrophilic Addition of Epoxides to Alkenes: [3+2] Cycloadditions Catalyzed by Lewis Acids

W. G. Shuler, L. A. Combee, I. D. Falk, M. K. Hilinski, Eur. J. Org. Chem. 2016, 3335–3338.