Dr STEPHEN ARGENT's Outputs (74)

A Modular and Scalable Route to Protected Cyclopropane Amino Acid Building Blocks (2025)
Journal Article
Swan, C. T., Edmonds, A. G., Argent, S. P., & Mitchell, N. J. (2025). A Modular and Scalable Route to Protected Cyclopropane Amino Acid Building Blocks. Organic Letters, 27(18), 4800-4805. https://doi.org/10.1021/acs.orglett.5c01341

An improved method for the synthesis of noncanonical cyclopropane amino acids from common laboratory reagents is described, avoiding the use of neurotoxic oxidants or precious metal catalysts. Intramolecular isocyanate trapping via a Hofmann rearrang... Read More about A Modular and Scalable Route to Protected Cyclopropane Amino Acid Building Blocks.

A nanoscale chemical oscillator: reversible formation of palladium nanoparticles in ionic liquid (2025)
Journal Article
Lodge, R. W., Cull, W. J., Weilhard, A., Argent, S. P., Alves Fernandes, J., & Khlobystov, A. N. (2025). A nanoscale chemical oscillator: reversible formation of palladium nanoparticles in ionic liquid. Nanoscale, 17(16), 10105-10116. https://doi.org/10.1039/D4NR04150J

From the theory of chaos-to-order transitions to the origins of life on Earth, oscillating chemical reactions play a fundamental role in nature. This study demonstrates how chemical oscillators can exist at the nanoscale, bridging the gap between mol... Read More about A nanoscale chemical oscillator: reversible formation of palladium nanoparticles in ionic liquid.

Gold(I)‐Catalyzed Nucleophilic Propargylation of Azinium Ions via Hydroxydihydroazine Intermediates (2025)
Journal Article
Smithson, J., O'Brien, L., Jones, K. D., Argent, S. P., Wheelhouse, K. M., Woodward, S., Ermanis, K., & Lam, H. W. (2025). Gold(I)‐Catalyzed Nucleophilic Propargylation of Azinium Ions via Hydroxydihydroazine Intermediates. Chemistry - A European Journal, 31(9), Article e202404153. https://doi.org/10.1002/chem.202404153

The nucleophilic propargylation of azinium ions with a propargylboronate proceeds efficiently under gold(I) catalysis. A range of N-alkylated pyridinium, quinolinium, and pyrazinium ions undergo propargylation with good yields and high regioselectivi... Read More about Gold(I)‐Catalyzed Nucleophilic Propargylation of Azinium Ions via Hydroxydihydroazine Intermediates.

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.

Synthesis of the Bulky Phosphanide [P(SiiPr3)2]− and Its Stabilization of Low-Coordinate Group 12 Complexes (2024)
Journal Article
Churchill, O. P., Dase, A., Taylor, L. J., Argent, S. P., Coles, N. T., Walker, G. S., & Kays, D. L. (2024). Synthesis of the Bulky Phosphanide [P(SiiPr3)2]− and Its Stabilization of Low-Coordinate Group 12 Complexes. Inorganic Chemistry, 63(43), 20286-20294. https://doi.org/10.1021/acs.inorgchem.4c03134

Here, we report an improved synthesis of the bulky phosphanide anion [P(SiiPr3)2]− in synthetically useful yields and its complexation to group 12 metals. The ligand is obtained as the sodium salt NaP(SiiPr3)2 1 in a 42% isolated yield and a single s... Read More about Synthesis of the Bulky Phosphanide [P(SiiPr3)2]− and Its Stabilization of Low-Coordinate Group 12 Complexes.

Structural Transformations of Metal-Organic Cages through Tetrazine-Alkene Reactivity (2024)
Journal Article
Black, M. R., Bhattacharyya, S., Argent, S. P., & Pilgrim, B. S. (2024). Structural Transformations of Metal-Organic Cages through Tetrazine-Alkene Reactivity. Journal of the American Chemical Society, 146(41), 28233-28241. https://doi.org/10.1021/jacs.4c08591

The assembly of metal-organic cages is governed by metal ion coordination preferences and the geometries of the typically rigid and planar precursor ligands. PdnL2n cages are among the most structurally diverse, with subtle differences in the metal-l... Read More about Structural Transformations of Metal-Organic Cages through Tetrazine-Alkene Reactivity.

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

Organofunctionalized borotungstate polyoxometalates as tunable photocatalysts for oxidative dimerization of amines (2024)
Journal Article
Tsang, N., Kibler, A. J., Argent, S. P., Lam, H. W., Jones, K. D., & Newton, G. N. (2024). Organofunctionalized borotungstate polyoxometalates as tunable photocatalysts for oxidative dimerization of amines. Chemical Science, 15(36), 14685-14691. https://doi.org/10.1039/d4sc03534h

Organofunctionalized borotungstate Keggin polyoxometalates, (nBu4N)3H[HBW11O39(P(O)Ph)2] (PBW11), (nBu4N)3H[HBW11O39(As(O)Ph)2] (AsBW11), and (nBu4N)4[HBW11O39(PhSiOSiPh)] (SiBW11), were synthesized and structurally characterized. Cyclic voltammetry... Read More about Organofunctionalized borotungstate polyoxometalates as tunable photocatalysts for oxidative dimerization of amines.

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, 136(40), Article e202410954. https://doi.org/10.1002/ange.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)
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.

Controlling Noncollinear Ferromagnetism in van der Waals Metal-Organic Magnets (2024)
Journal Article
Pitcairn, J., Ongkiko, M. A., Iliceto, A., Speakman, P. J., Calder, S., Cochran, M. J., Paddison, J. A., Liu, C., Argent, S. P., Morris, A. J., & Cliffe, M. J. (2024). Controlling Noncollinear Ferromagnetism in van der Waals Metal-Organic Magnets. Journal of the American Chemical Society, 146(28), 19146–19159. https://doi.org/10.1021/jacs.4c04102

Van der Waals (vdW) magnets both allow exploration of fundamental 2D physics and offer a route toward exploiting magnetism in next generation information technology, but vdW magnets with complex, noncollinear spin textures are currently rare. We repo... Read More about Controlling Noncollinear Ferromagnetism in van der Waals Metal-Organic Magnets.

Benzene-1,2,4,5-tetrol (2024)
Journal Article
Weare, B. L., Hoggett, S., Cull, W. J., Argent, S. P., Khlobystov, A. N., & Brown, P. D. (2024). Benzene-1,2,4,5-tetrol. IUCrData, 9(6), Article x240612. https://doi.org/10.1107/S2414314624006126

The crystal structure of the title compound was determined at 120 K. It crystallizes in the triclinic space group P\overline{1} with four independent molecules in the asymmetric unit. In the crystal, each symmetry-unique molecule forms π–π stacks on... Read More about Benzene-1,2,4,5-tetrol.

Total synthesis, biological evaluation and biosynthetic re-evaluation of Illicium-derived neolignans (2024)
Journal Article
Arnold, R. E., Saska, J., Mesquita-Ribeiro, R., Dajas-Bailador, F., Taylor, L., Lewis, W., Argent, S., Shao, H., Houk, K. N., & Denton, R. M. (2024). Total synthesis, biological evaluation and biosynthetic re-evaluation of Illicium-derived neolignans. Chemical Science, 15(30), 11783-11793. https://doi.org/10.1039/d4sc03232b

We report the first total syntheses of simonsol F (3), simonsinol (5), fargenin (4), and macranthol (6) in addition to syntheses of simonsol C (2), simonsol G (1), and honokiol (14). The syntheses are based upon a phosphonium ylide-mediated cascade r... Read More about Total synthesis, biological evaluation and biosynthetic re-evaluation of Illicium-derived neolignans.

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. (in press). 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.

Porous isoreticular non-metal organic frameworks (2024)
Journal Article
O’Shaughnessy, M., Glover, J., Hafizi, R., Barhi, M., Clowes, R., Chong, S. Y., Argent, S. P., Day, G. M., & Cooper, A. I. (2024). Porous isoreticular non-metal organic frameworks. Nature, 630(8015), 102-108. https://doi.org/10.1038/s41586-024-07353-9

Metal–organic frameworks (MOFs) are useful synthetic materials that are built by the programmed assembly of metal nodes and organic linkers1. The success of MOFs results from the isoreticular principle2, which allows families of structurally analogou... Read More about Porous isoreticular non-metal organic frameworks.

Enantioselective de novo synthesis of 14-hydroxy-6-oxomorphinans (2024)
Journal Article
Moore, J. C., Modell, L., Glenn, J. R., Jones, K. D., Argent, S. P., Lane, J. R., Canals, M., & Lam, H. W. (2024). Enantioselective de novo synthesis of 14-hydroxy-6-oxomorphinans. Chemical Communications, 60(47), 6007-6010. https://doi.org/10.1039/d4cc01788a

The enantioselective de novo synthesis of pharmacologically important 14-hydroxy-6-oxomorphinans is described. 4,5-Desoxynaltrexone and 4,5-desoxynaloxone were prepared using this route and their biological activities against the opioid receptors wer... Read More about Enantioselective de novo synthesis of 14-hydroxy-6-oxomorphinans.

Mechanistic investigations of the Fe(ii) mediated synthesis of squaraines (2024)
Journal Article
Liu, Y., Coles, N. T., Cajiao, N., Taylor, L. J., Davies, E. S., Barbour, A., Morgan, P. J., Butler, K., Pointer-Gleadhill, B., Argent, S. P., McMaster, J., Neidig, M. L., Robinson, D., & Kays, D. L. (2024). Mechanistic investigations of the Fe(ii) mediated synthesis of squaraines. Chemical Science, 15(25), 9599-9611. https://doi.org/10.1039/D4SC01286K

The scission and homologation of CO is a fundamental process in the Fischer–Tropsch reaction. However, given the heterogeneous nature of the catalyst and forcing reaction conditions, it is difficult to determine the intermediates of this reaction. He... Read More about Mechanistic investigations of the Fe(ii) mediated synthesis of squaraines.

Iodoetherification as a strategy towards sp 3-rich scaffolds for drug discovery (2024)
Journal Article
Barnes, L., Birkinshaw, T. N., Senior, A. J., Siles Brügge, O., Lewis, W., Argent, S. P., Moody, C. J., & Nortcliffe, A. (2024). Iodoetherification as a strategy towards sp 3-rich scaffolds for drug discovery. Bioorganic and Medicinal Chemistry, 101, Article 117636. https://doi.org/10.1016/j.bmc.2024.117636

Functionalised tetrahydropyran and spirooxepane scaffolds were prepared utilising an iodoetherification strategy and elaborated to demonstrate their potential use in library synthesis. The iodoetherification products could be readily transformed to t... Read More about Iodoetherification as a strategy towards sp 3-rich scaffolds for drug discovery.

Probing the Mechanism of Action of Bis(phenolato) Amine (ONO Donor Set) Titanium(IV) Anticancer Agents (2024)
Journal Article
Musa, M., Abid, M., Bradshaw, T. D., Boocock, D. J., Coveney, C., Argent, S. P., & Woodward, S. (2024). Probing the Mechanism of Action of Bis(phenolato) Amine (ONO Donor Set) Titanium(IV) Anticancer Agents. Journal of Medicinal Chemistry, 67(4), 2732-2744. https://doi.org/10.1021/acs.jmedchem.3c01874

The need for anticancer therapies that overcome metallodrug resistance while minimizing adverse toxicities is targeted, herein, using titanium coordination complexes. Octahedral titanium­(IV) trans, mer-[Ti­{R1N­(CH2–2-MeO-4-R1-C6H2)2}2] [R1 = Et, al... Read More about Probing the Mechanism of Action of Bis(phenolato) Amine (ONO Donor Set) Titanium(IV) Anticancer Agents.

Selective electrochemical CO 2 conversion with a hybrid polyoxometalate (2023)
Journal Article
Kuramochi, S., Cameron, J. M., Fukui, T., Jones, K. D., Argent, S. P., Kusaka, S., Shiraishi, R., Tamaki, Y., Yatsu, T., Shiga, T., Ishitani, O., Oshio, H., & Newton, G. N. (2023). Selective electrochemical CO 2 conversion with a hybrid polyoxometalate. Chemical Communications, 59(72), 10801-10804. https://doi.org/10.1039/d3cc02138f

A multi-component coordination compound, in which ruthenium antenna complexes are connected to a polyoxotungstate core is presented. This hybrid cluster effectively promotes the electrochemical conversion of CO2 to C1 feedstocks, the selectivity of w... Read More about Selective electrochemical CO 2 conversion with a hybrid polyoxometalate.