innovations in bioactive small molecule synthesis

publications

C-H functionalization
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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!

about us

We are a synthetic organic chemistry research laboratory at the University of Virginia.

© Copyright 2021 Michael Hilinski
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publications

A First-in-Class Small Molecule Inhibitor Targeting AVIL Exhibits Safety and Antitumor Efficacy in Preclinical Models of Glioblastoma

Z. Xie, P. L. Janczyk, R. Cornelison, S. Lynch, B. Leifer, P. Hahn, J. D. Dooley, A. Fierti, X. Shi, Z. Zhang, T. Li, Q. Wang, A. Zhang, M. Glowczyk, L. Marrah, A. Koeler, J. W. Mandell, M. Hilinski, H. Li, Sci. Transl. Med. 2026, 18, eadt1211.

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.

Organocatalytic Olefin Aziridination via Iminium-Catalyzed Nitrene Transfer: Scope, Limitations, and Mechanistic Insight

S. L. Johnson and M. K. Hilinski, J. Org. Chem. 2019, 84, 8589-8595.

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 Nitrenoid Transfer: Metal-Free Selective Intermolecular C(sp3)-H Amination Catalyzed by an Iminium Salt

L. A. Combee, B. Raya, D. Wang, M. K. Hilinski, Chem. Sci. 2018, 9, 935-939.

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.

Chemoselective Hydroxylation of Aliphatic sp3 C–H Bonds Using a Ketone Catalyst and Aqueous H2O2

C. J. Pierce, M. K. Hilinski, Org. Lett. 2014, 16, 6504–6507.