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Programmable Deuteration of Indoles via Reverse Deuterium Exchange (2023)
Journal Article
Fitzgerald, L. S., McNulty, R. L., Greener, A., & O'Duill, M. L. (2023). Programmable Deuteration of Indoles via Reverse Deuterium Exchange. Journal of Organic Chemistry, 88(15), 10772-10776. https://doi.org/10.1021/acs.joc.3c00819

Methods for selective deuterium incorporation into drug-like molecules have become extremely valuable due to the commercial, mechanistic, and biological importance of deuterated compounds. Herein, we report a programmable labeling platform that allow... Read More about Programmable Deuteration of Indoles via Reverse Deuterium Exchange.

Undirected, Pd-catalysed deuteration of indoles with programmable regioselectivity (2022)
Working Paper
Fitzgerald, L., McNulty, R., Greener, A., & O'Duill, M. Undirected, Pd-catalysed deuteration of indoles with programmable regioselectivity

Methods for selective deuterium-incorporation into drug-like molecules have become extremely valuable due to the commercial and biological importance of deuterated compounds. Selective C2-deuteration of indoles currently requires the installation of... Read More about Undirected, Pd-catalysed deuteration of indoles with programmable regioselectivity.

A Guide to Directing Group Removal: 8?Aminoquinoline (2021)
Journal Article
Fitzgerald, L. S., & O'Duill, M. L. (2021). A Guide to Directing Group Removal: 8?Aminoquinoline. Chemistry - A European Journal, 27(33), 8411-8436. https://doi.org/10.1002/chem.202100093

The use of directing groups allows high levels of selectivity to be achieved in transition metal‐catalyzed transformations. Efficient removal of these auxiliaries after successful functionalization, however, can be very challenging. This review provi... Read More about A Guide to Directing Group Removal: 8?Aminoquinoline.

Controlling the crystal structure of precisely spaced polyethylene-like polyphosphoesters (2020)
Journal Article
Haider, T., Suraeva, O., O’Duill, M. L., Mars, J., Mezger, M., Lieberwirth, I., & Wurm, F. R. (2020). Controlling the crystal structure of precisely spaced polyethylene-like polyphosphoesters. Polymer Chemistry, 11(20), 3404-3415. https://doi.org/10.1039/d0py00272k

Understanding polymer crystallization is important for polyethylene-like materials. A small fraction of monomers with functional groups within the polyethylene chain can act as crystallization “defects”. Such defects can be used to control the crysta... Read More about Controlling the crystal structure of precisely spaced polyethylene-like polyphosphoesters.

Protodepalladation as a Strategic Elementary Step in Catalysis (2018)
Journal Article
Engle, K., & O’Duill, M. (2018). Protodepalladation as a Strategic Elementary Step in Catalysis. SYNTHESIS, 50(24), 4699-4714. https://doi.org/10.1055/s-0037-1611064

Protodepalladation is the redox-neutral conversion of a C–Pd(II) bond into a C–H bond via reaction with a Brønsted acid. It is the microscopic reverse of Pd(II)-mediated C–H cleavage. In the context of catalytic reaction development, protodepalladati... Read More about Protodepalladation as a Strategic Elementary Step in Catalysis.

Cross-Coupling of [2-Aryl-1,1,2,2-tetrafluoroethyl](trimethyl)silanes with Aryl Halides (2015)
Journal Article
O’Duill, M., Dubost, E., Pfeifer, L., & Gouverneur, V. (2015). Cross-Coupling of [2-Aryl-1,1,2,2-tetrafluoroethyl](trimethyl)silanes with Aryl Halides. Organic Letters, 17(14), 3466-3469. https://doi.org/10.1021/acs.orglett.5b01510

The synthesis of arylCF2CF2SiMe3 and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-arylethanes is reported. The use of pyridine as an alternative to phenanthroline, and t... Read More about Cross-Coupling of [2-Aryl-1,1,2,2-tetrafluoroethyl](trimethyl)silanes with Aryl Halides.

Recruitment and Immobilization of a Fluorinated Biomarker Across an Interfacial Phospholipid Film using a Fluorocarbon Gas (2015)
Journal Article
Yang, G., O'Duill, M., Gouverneur, V., & Krafft, M. P. (2015). Recruitment and Immobilization of a Fluorinated Biomarker Across an Interfacial Phospholipid Film using a Fluorocarbon Gas. Angewandte Chemie, 127(29), 8522-8526. https://doi.org/10.1002/ange.201502677

Perfluorohexane gas when introduced in the air atmosphere above a film of phospholipid self-supported on an aqueous solution of C2F5-labeled compounds causes the recruitment and immobilization of the latter in the interfacial film. When the phospholi... Read More about Recruitment and Immobilization of a Fluorinated Biomarker Across an Interfacial Phospholipid Film using a Fluorocarbon Gas.

Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes (2013)
Journal Article
Mizuta, S., S. R. Stenhagen, I., O’Duill, M., Wolstenhulme, J., K. Kirjavainen, A., J. Forsback, S., …Gouverneur, V. (2013). Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes. Organic Letters, 15(11), 2648-2651. https://doi.org/10.1021/ol4009377

Treatment of readily available α,α-difluoro- and α-fluoroarylacetic acids with Selectfluor under Ag(I) catalysis led to decarboxylative fluorination. This operationally simple reaction gave access to tri- and difluoromethylarenes applying a late-stag... Read More about Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes.

Trifluoromethylation of Allylsilanes under Photoredox Catalysis (2013)
Journal Article
Mizuta, S., Engle, K. M., Verhoog, S., Galicia-López, O., O’Duill, M., Médebielle, M., …Gouverneur, V. (2013). Trifluoromethylation of Allylsilanes under Photoredox Catalysis. Organic Letters, 15(6), 1250–1253. https://doi.org/10.1021/ol400184t

A new catalytic method to access allylic secondary CF3 products is described. These reactions use the visible light excited Ru(bpy)3Cl2·6H2O catalyst and the Togni or Umemoto reagent as the CF3 source. The photoredox catalytic manifold delivers enant... Read More about Trifluoromethylation of Allylsilanes under Photoredox Catalysis.

Catalytic Hydrotrifluoromethylation of Unactivated Alkenes (2013)
Journal Article
Mizuta, S., Verhoog, S., Engle, K. M., Khotavivattana, T., O’Duill, M., Wheelhouse, K., …Gouverneur, V. (2013). Catalytic Hydrotrifluoromethylation of Unactivated Alkenes. Journal of the American Chemical Society, 135(7), 2505–2508. https://doi.org/10.1021/ja401022x

A visible-light-mediated hydrotrifluoromethylation of unactivated alkenes that uses the Umemoto reagent as the CF3 source and MeOH as the reductant is disclosed. This effective transformation operates at room temperature in the presence of 5 mol % Ru... Read More about Catalytic Hydrotrifluoromethylation of Unactivated Alkenes.