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Dr MIRIAM O'DUILL's Outputs (21)

Structure and thermal stability of phosphorus-iodonium ylids (2024)
Journal Article
Greener, A., Argent, S. P., Clarke, C. J., & O’Duill, M. L. (2024). Structure and thermal stability of phosphorus-iodonium ylids. Beilstein Journal of Organic Chemistry, 20, 2931-2939. https://doi.org/10.3762/bjoc.20.245

Hypervalent iodine(III) reagents have become indispensable tools in organic synthesis, but gaps remain in the functionalities they
can transfer. In this study, a fundamental understanding of the thermal stability of phosphorus-iodonium ylids is obta... Read More about Structure and thermal stability of phosphorus-iodonium ylids.

Structure and thermal stability of phosphorus-iodonium ylids (2024)
Preprint / Working Paper
Greener, A., P. Argent, S., Clarke, C., & L. O'Duill, M. Structure and thermal stability of phosphorus-iodonium ylids

Hypervalent iodine(III) reagents have become indispensable tools in organic synthesis, but gaps remain in the functionalities they can transfer. In this study, a fundamental understanding of the thermal stability of phosphorus-iodonium ylids is obtai... Read More about Structure and thermal stability of phosphorus-iodonium ylids.

2,2‐Difluoroethylation of Heteroatom Nucleophiles via a Hypervalent Iodine Strategy (2024)
Journal Article
Das, S., McIvor, C., Greener, A., Suwita, C., Argent, S. P., & O'Duill, M. L. (2024). 2,2‐Difluoroethylation of Heteroatom Nucleophiles via a Hypervalent Iodine Strategy. Angewandte Chemie International Edition, 63(40), Article e202410954. https://doi.org/10.1002/anie.202410954

The 2,2-difluoroethyl group is an important lipophilic hydrogen bond donor in medicinal chemistry, but its incorporation into small molecules is often challenging. Herein, we demonstrate electrophilic 2,2-difluoroethylation of thiol, amine and alcoho... Read More about 2,2‐Difluoroethylation of Heteroatom Nucleophiles via a Hypervalent Iodine Strategy.

2,2-Difluoroethylation of heteroatom nucleophiles via a hypervalent iodine strategy (2024)
Preprint / Working Paper
Das, S., McIvor, C., Greener, A., Suwita, C., Argent, S., & O'Duill, M. 2,2-Difluoroethylation of heteroatom nucleophiles via a hypervalent iodine strategy

The 2,2-difluoroethyl group is an important lipophilic hydrogen bond donor in medicinal chemistry, but its incorporation into small molecules is often challenging. Herein, we demonstrate electrophilic 2,2 difluoroethylation of thiol, amine and alcoho... Read More about 2,2-Difluoroethylation of heteroatom nucleophiles via a hypervalent iodine strategy.

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)
Preprint / 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.

Copper-Catalyzed Chan–Lam Cyclopropylation of Phenols and Azaheterocycles (2018)
Journal Article
Derosa, J., O’Duill, M. L., Holcomb, M., Boulous, M. N., Patman, R. L., Wang, F., Tran-Dubé, M., McAlpine, I., & Engle, K. M. (2018). Copper-Catalyzed Chan–Lam Cyclopropylation of Phenols and Azaheterocycles. Journal of Organic Chemistry, 83(7), 3417-3425. https://doi.org/10.1021/acs.joc.7b03100

Small molecules containing cyclopropane-heteroatom linkages are commonly needed in medicinal chemistry campaigns yet are problematic to prepare using existing methods. To address this issue, a scalable Chan-Lam cyclopropylation reaction using potassi... Read More about Copper-Catalyzed Chan–Lam Cyclopropylation of Phenols and Azaheterocycles.

Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization (2017)
Journal Article
O’Duill, M. L., Matsuura, R., Wang, Y., Turnbull, J. L., Gurak, J. A., Gao, D.-W., Lu, G., Liu, P., & Engle, K. M. (2017). Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization. Journal of the American Chemical Society, 139(44), 15576-15579. https://doi.org/10.1021/jacs.7b08383

Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselectiv... Read More about Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization.

Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl (2017)
Journal Article
Derosa, J., Cantu, A. L., Boulous, M. N., O’Duill, M. L., Turnbull, J. L., Liu, Z., De La Torre, D. M., & Engle, K. M. (2017). Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl. Journal of the American Chemical Society, 139(14), 5183-5193. https://doi.org/10.1021/jacs.7b00892

A regioselective anti-hydrochlorination of unactivated alkynes is reported. The reaction utilizes in situ generated HCl as the source of both the Cl - and H + and is catalyzed by palladium(II) acetate, with loadings as low as 25 ppm. Removable picoli... Read More about Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl.

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 International Edition, 54(29), 8402-8406. https://doi.org/10.1002/anie.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.

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., Tredwell, M., Sandford, G., R. Moore, P., Huiban, M., K. Luthra, S., Passchier, J., Solin, O., & 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., Wheelhouse, K., Rassias, G., Thompson, A. L., & 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.