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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., …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.

Organoruthenium Complexes Containing Phosphinodicarboxamide Ligands (2023)
Journal Article
Nolla-Saltiel, R., Geer, A. M., Sharpe, H. R., Huke, C. D., Taylor, L. J., Linford-Wood, T. G., …Kays, D. L. (2023). Organoruthenium Complexes Containing Phosphinodicarboxamide Ligands. Inorganics, 11(9), Article 372. https://doi.org/10.3390/inorganics11090372

Ruthenium complexes of phosphinocarboxamide ligands, and their use to form metallacycles using halide abstraction/deprotonation reactions are reported. Thus, [Ru(p-cym){PPh2C(=O)NHR}Cl2; R = iPr (1), Ph (2), p-tol (3)] and [Ru(p-cym){PPh2C(=O)N(R)C(=... Read More about Organoruthenium Complexes Containing Phosphinodicarboxamide Ligands.

General Method for the Asymmetric Synthesis of N–H Sulfoximines via C–S Bond Formation (2020)
Journal Article
Mendonça Matos, P., Lewis, W., Argent, S. P., Moore, J. C., & Stockman, R. A. (in press). General Method for the Asymmetric Synthesis of N–H Sulfoximines via C–S Bond Formation. Organic Letters, 22(7), 2776-2780. https://doi.org/10.1021/acs.orglett.0c00761

A versatile method for the synthesis of enantioenriched N–H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent st... Read More about General Method for the Asymmetric Synthesis of N–H Sulfoximines via C–S Bond Formation.

Modular bismacycles for the selective C–H arylation of phenols and naphthols (2020)
Journal Article
Jurrat, M., Maggi, L., Lewis, W., & Ball, L. T. (2020). Modular bismacycles for the selective C–H arylation of phenols and naphthols. Nature Chemistry, 12(3), 260-269. https://doi.org/10.1038/s41557-020-0425-4

Given the important role played by 2-hydroxybiaryls in organic, medicinal and materials chemistry, concise methods for the synthesis of this common motif are extremely valuable. In seeking to extend the synthetic chemists’ lexicon in this regard,... Read More about Modular bismacycles for the selective C–H arylation of phenols and naphthols.

Influence of molecular design on radical spin multiplicity: characterisation of BODIPY dyad and triad radical anions (2020)
Journal Article
Mangham, B., Hanson-Heine, M. W. D., Davies, E. S., Wriglesworth, A., George, M. W., Lewis, W., …Champness, N. R. (2020). Influence of molecular design on radical spin multiplicity: characterisation of BODIPY dyad and triad radical anions. Physical Chemistry Chemical Physics, 22(8), 4429-4438. https://doi.org/10.1039/c9cp06427c

This journal is © the Owner Societies. A strategy to create organic molecules with high degrees of radical spin multiplicity is reported in which molecular design is correlated with the behaviour of radical anions in a series of BODIPY dyads. Upon re... Read More about Influence of molecular design on radical spin multiplicity: characterisation of BODIPY dyad and triad radical anions.

Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(I) migration (2019)
Journal Article
O'Brien, L., Karad, S. N., Lewis, W., & Lam, H. W. (2019). Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(I) migration. Chemical Communications, 55(76), 11366-11369. https://doi.org/10.1039/c9cc05205d

The synthesis of functionalized 1-tetralones by the rhodium(I)-catalyzed reaction of alkynyl malonates with arylboronic acids is described. These arylative cyclizations proceed via an alkenyl-to-aryl 1,4-Rh(I) migration as a key step. Preliminary res... Read More about Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(I) migration.

Developing a sustainable route to environmentally relevant metal-organic frameworks: ultra-rapid synthesis of MFM-300(Al) using microwave heating (2019)
Journal Article
Thomas-Hillman, I., Stevens, L. A., Lange, M., Möllmer, J., Lewis, W., Dodds, C., …Laybourn, A. (2019). Developing a sustainable route to environmentally relevant metal-organic frameworks: ultra-rapid synthesis of MFM-300(Al) using microwave heating. Green Chemistry, 21(18), 5039-5045. https://doi.org/10.1039/c9gc02375e

NO2, SO2 and CO2 are major air pollutants causing significant environmental and health problems. Metal-organic frameworks (MOFs), in particular [Al2(OH)2(C16O8H6)](H2O)6 (trivial names: NOTT-300/MFM-300(Al)), have shown great promise for capturing th... Read More about Developing a sustainable route to environmentally relevant metal-organic frameworks: ultra-rapid synthesis of MFM-300(Al) using microwave heating.

Ground and Excited States of Bis?4?Methoxybenzyl?Substituted Diketopyrrolopyrroles: Spectroscopic and Electrochemical Studies (2019)
Journal Article
Murphy, A. S., Killalea, C. E., Humphreys, J., Hume, P. A., Cliffe, M. J., Murray, G. J., …Amabilino, D. B. (2019). Ground and Excited States of Bis‐4‐Methoxybenzyl‐Substituted Diketopyrrolopyrroles: Spectroscopic and Electrochemical Studies. ChemPlusChem, 84(9), 1413-1422. https://doi.org/10.1002/cplu.201900286

A series of symmetrically bis?4?methoxybenzyl (4MB) N?substituted 1,4?diketopyrrolo[3,4?c]pyrrole (DPP) derivatives have been synthesized. The 4MB unit makes the DPP core soluble, and shows subtle modification of up to 0.2?eV in ground and excited st... Read More about Ground and Excited States of Bis?4?Methoxybenzyl?Substituted Diketopyrrolopyrroles: Spectroscopic and Electrochemical Studies.

Tripodal O-N-O bis-Phenolato Amine Titanium(IV) Complexes Show High In Vitro Anti-Cancer Activity (2019)
Journal Article
Abid, M., Nouch, R., Bradshaw, T. D., Lewis, W., & Woodward, S. (2019). Tripodal O-N-O bis-Phenolato Amine Titanium(IV) Complexes Show High In Vitro Anti-Cancer Activity. European Journal of Inorganic Chemistry, 2019(22), 2774-2780. https://doi.org/10.1002/ejic.201900510

The octahedral titanium(IV) complexes trans,mer‐[Ti{R3N(CH2C6H2‐2‐O‐4‐R2‐6‐R1)2}2] (R1 = Me, OMe, Cl; R2 = Me, OMe, F, Cl; R3 = Me, Et; not all combinations) are synthesised in two steps from simple phenols in 36‐53% overall yield. The highly crystal... Read More about Tripodal O-N-O bis-Phenolato Amine Titanium(IV) Complexes Show High In Vitro Anti-Cancer Activity.

A Highly Active Bidentate Magnesium Catalyst for Amine‐Borane Dehydrocoupling: Kinetic and Mechanistic Studies (2019)
Journal Article
Ried, A., Taylor, L., Geer, A., Williams, H., Lewis, W., Blake, A., & Kays, D. L. (2019). A Highly Active Bidentate Magnesium Catalyst for Amine‐Borane Dehydrocoupling: Kinetic and Mechanistic Studies. Chemistry - A European Journal, 25(27), 6840-6846. https://doi.org/10.1002/chem.201901197

A magnesium complex (1) featuring a bidentate aminopyridinato ligand is a remarkably selective catalyst for the dehydrocoupling of amine-boranes. This reaction proceeds to completion with low catalyst loadings (1 mol%) und... Read More about A Highly Active Bidentate Magnesium Catalyst for Amine‐Borane Dehydrocoupling: Kinetic and Mechanistic Studies.

Restricting shuttling in bis(imidazolium)…pillar[5]arene rotaxanes using metal coordination (2018)
Journal Article
Langer, P., Yang, L., Pfeiffer, C. R., Lewis, W., & Champness, N. R. (2018). Restricting shuttling in bis(imidazolium)…pillar[5]arene rotaxanes using metal coordination. Dalton Transactions, 48(1), 58-64. https://doi.org/10.1039/c8dt04096f

Metal coordination to a series of bis(imidazolium)…pillar[5]arene [2]rotaxanes through the formation of metal-carbene bonds facilitates a new strategy to restrict the shuttling motion in [2]rotaxanes. Whereas the pillar[5]arene macrocycle rapidly shu... Read More about Restricting shuttling in bis(imidazolium)…pillar[5]arene rotaxanes using metal coordination.

Thionated perylene diimide–phenothiazine dyad: synthesis, structure, and electrochemical studies (2018)
Journal Article
Pearce, N., Davies, E. S., Lewis, W., & Champness, N. R. (2018). Thionated perylene diimide–phenothiazine dyad: synthesis, structure, and electrochemical studies. ACS Omega, 3(10), 14236-14244. https://doi.org/10.1021/acsomega.8b02457

Perylene diimides (PDIs) are promising candidates for n-type semiconductor materials and, thus, for use in organic electronics. Thionation of the imide moiety provides an e?cient strategy to control the donor?acceptor gap of these types of compounds... Read More about Thionated perylene diimide–phenothiazine dyad: synthesis, structure, and electrochemical studies.

Controlling the two-dimensional self-assembly of functionalized porphyrins via adenine–thymine Quartet formation (2018)
Journal Article
Blunt, M. O., Hu, Y., Toft, C. W., Slater, A. G., Lewis, W., & Champness, N. R. (2018). Controlling the two-dimensional self-assembly of functionalized porphyrins via adenine–thymine Quartet formation. Journal of Physical Chemistry C, 122(45), 26070-26079. https://doi.org/10.1021/acs.jpcc.8b08888

The development of supramolecular synthons capable of driving hierarchical two-dimensional (2D) self-assembly is an important step toward the growth of complex and functional molecular surfaces. In this work, the formation of nucleobase quartets cons... Read More about Controlling the two-dimensional self-assembly of functionalized porphyrins via adenine–thymine Quartet formation.

PdII-Mediated Oxidative Amination for Access to a 9-Azabicyclo[4.2.1]nonane Compound Library and Anatoxin-a (2018)
Journal Article
Dawood, R. S., Chidipudi, S. R., O'Connor, D. C., Lewis, W., Hamza, D., Pearce, C. A., …Stockman, R. A. (2018). PdII-Mediated Oxidative Amination for Access to a 9-Azabicyclo[4.2.1]nonane Compound Library and Anatoxin-a. European Journal of Organic Chemistry, 2018(40), 5558-5561. https://doi.org/10.1002/ejoc.201801209

© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Intramolecular oxidative amination of readily accessible aminocyclooct-4-enes provides rapid and regioselective access to the 9-azabicyclo[4.2.1]nonane framework characteristic of the natural produc... Read More about PdII-Mediated Oxidative Amination for Access to a 9-Azabicyclo[4.2.1]nonane Compound Library and Anatoxin-a.

Host–guest selectivity in a series of isoreticular metal–organic frameworks: observation of acetylene-to-alkyne and carbon dioxide-to-amide interactions (2018)
Journal Article
Humby, J. D., Benson, O., Smith, G. L., Argent, S. P., da Silva, I., Cheng, Y., …Schröder, M. (2018). Host–guest selectivity in a series of isoreticular metal–organic frameworks: observation of acetylene-to-alkyne and carbon dioxide-to-amide interactions. Chemical Science, 10(4), 1098-1106. https://doi.org/10.1039/c8sc03622e

In order to develop new porous materials for applications in gas separations such as natural gas upgrading, landfill gas processing and acetylene purification it is vital to gain understanding of host-substrate interactions at a molecular level. Here... Read More about Host–guest selectivity in a series of isoreticular metal–organic frameworks: observation of acetylene-to-alkyne and carbon dioxide-to-amide interactions.

Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols (2018)
Journal Article
Panchal, H., Clarke, C., Bell, C., Karad, S. N., Lewis, W., & Lam, H. W. (2018). Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols. Chemical Communications, 54(87), 12389-12392. https://doi.org/10.1039/c8cc06388e

Nickel-catalyzed, highly diastereoselective annulations between activated allenes and 2-acetylarylboronic acid or 2-formylarylboronic acids are reported. No ligand for nickel is required, and the reactions proceed efficiently at room temperature to g... Read More about Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols.

Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative cyclizations of N-tosyl alkynamides (2018)
Journal Article
Gillbard, S. M., Chung, C., Karad, S. N., Panchal, H., Lewis, W., & Lam, H. W. (2018). Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative cyclizations of N-tosyl alkynamides. Chemical Communications, 54(83), 11769-11772. doi:10.1039/c8cc06649c

The synthesis of multisubstituted pyrroles by the nickel-catalyzed reaction of N-tosylalkynamides with arylboronic acids is reported. These reactions are triggered by alkyne arylnickelation, followed by cyclization of the resulting alkenylnickel spec... Read More about Synthesis of multisubstituted pyrroles by nickel-catalyzed arylative cyclizations of N-tosyl alkynamides.

Selective reduction and homologation of carbon monoxide by organometallic iron complexes (2018)
Journal Article
Sharpe, H. R., Geer, A. M., Taylor, L. J., Gridley, B. M., Blundell, T. J., Blake, A. J., …Kays, D. L. (2018). Selective reduction and homologation of carbon monoxide by organometallic iron complexes. Nature Communications, 9, Article 3757. https://doi.org/10.1038/s41467-018-06242-w

Carbon monoxide is a key C1 feedstock for the industrial production of hydrocarbons, where it is used to make millions of tonnes of chemicals, fuels, and solvents per annum. Many transition metal complexes can coordinate CO2 but the formation of new... Read More about Selective reduction and homologation of carbon monoxide by organometallic iron complexes.

Combining continuous flow oscillatory baffled reactors and microwave heating: Process intensification and accelerated synthesis of metal-organic frameworks (2018)
Journal Article
Laybourn, A., López-Fernández, A. M., Thomas-Hillman, I., Katrib, J., Lewis, W., Dodds, C., …Kingman, S. W. (2019). Combining continuous flow oscillatory baffled reactors and microwave heating: Process intensification and accelerated synthesis of metal-organic frameworks. Chemical Engineering Journal, 356, 170-177. https://doi.org/10.1016/j.cej.2018.09.011

We have constructed a continuous flow oscillatory baffled reactor (CF-OBR) equipped with a homogeneous and controllable microwave applicator in an entirely novel design. This affords a new route to chemical production incorporating many of the princi... Read More about Combining continuous flow oscillatory baffled reactors and microwave heating: Process intensification and accelerated synthesis of metal-organic frameworks.

Influence of hydrogen-bonding interactions on nuclearity and structure of palladium tiara-like complexes (2018)
Journal Article
Martin, H. J., Pfeiffer, C. R., Davies, E. S., Davis, A. L., Lewis, W., & Champness, N. R. (2018). Influence of hydrogen-bonding interactions on nuclearity and structure of palladium tiara-like complexes. ACS Omega, 3(8), 8769-8776. https://doi.org/10.1021/acsomega.8b01133

The role of intramolecular hydrogen-bonding interactions upon the nuclearity of palladium tiara-like complexes is reported herein. The synthesis of three palladium tiaras is described with three related thiolate ligands that vary in their hydrogen-bo... Read More about Influence of hydrogen-bonding interactions on nuclearity and structure of palladium tiara-like complexes.