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Synthesis of 2-Arylphenols via Formal Bismuth(V)-Mediated C–O Arylation of Guaiacols (2025)
Journal Article
Ansarian, N. F., & Ball, L. T. (2025). Synthesis of 2-Arylphenols via Formal Bismuth(V)-Mediated C–O Arylation of Guaiacols. Organic Letters, 27(11), 2769-2774. https://doi.org/10.1021/acs.orglett.5c00593

We report a new C-O arylation strategy for the synthesis of 2-arylphenols from bio-abundant guaiacols. Functionalization of the strong C-O bond is achieved through a sequence of arylative dearomatization, mediated selectively by an electrophilic bism... Read More about Synthesis of 2-Arylphenols via Formal Bismuth(V)-Mediated C–O Arylation of Guaiacols.

Development and Scale-Up of a New Sulfone-Based Bismacycle as a Universal Precursor for Bi(V)-Mediated Electrophilic Arylation (2024)
Journal Article
Fox, A., & Ball, L. T. (2024). Development and Scale-Up of a New Sulfone-Based Bismacycle as a Universal Precursor for Bi(V)-Mediated Electrophilic Arylation. Organic Process Research and Development, 28(2), 632-639. https://doi.org/10.1021/acs.oprd.3c00509

The scope and practical utility of bismuth(V)-mediated electrophilic arylation have been greatly improved by the recent development of user-friendly protocols based on modular bismacycle reagents. Here, we report the scalable synthesis of a new bench... Read More about Development and Scale-Up of a New Sulfone-Based Bismacycle as a Universal Precursor for Bi(V)-Mediated Electrophilic Arylation.

Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Aryboronic Acids (2023)
Journal Article
Sivanandan, S. T., Guiry, P. J., Owen, B., & Ball, L. (2023). Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Aryboronic Acids. Journal of Organic Chemistry, 88(14), 9730-9736. https://doi.org/10.1021/acs.joc.3c00361

Bismacycles featuring a sulfone-bridged scaffold have recently been developed as versatile and convenient electrophilic arylating agents. Here, we report that the exocyclic aryl group, which is ultimately transferred to a nucleophilic coupling partne... Read More about Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Aryboronic Acids.

Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Arylboronic Acids (2023)
Journal Article
Sivanandan, S. T., Owen, B., Guiry, P. J., & Ball, L. T. (2023). Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Arylboronic Acids. Journal of Organic Chemistry, 88(14), 9730–9736. https://doi.org/10.1021/acs.joc.3c00361

Bismacycles featuring a sulfone-bridged scaffold have recently been developed as versatile and convenient electrophilic arylating agents. Here, we report that the exocyclic aryl group, which is ultimately transferred to a nucleophilic coupling partne... Read More about Synthesis of Highly Functionalized Bismacycles via Post-Transmetallation Modification of Arylboronic Acids.

Photochemically Mediated Ring Expansion of Indoles and Pyrroles with Chlorodiazirines: Synthetic Methodology and Thermal Hazard Assessment (2023)
Journal Article
Joynson, B. W., Cumming, G. R., & Ball, L. T. (2023). Photochemically Mediated Ring Expansion of Indoles and Pyrroles with Chlorodiazirines: Synthetic Methodology and Thermal Hazard Assessment. Angewandte Chemie International Edition, 62(31), Article e202305081. https://doi.org/10.1002/anie.202305081

We demonstrate that arylchlorodiazirines serve as photo-activated halocarbene precursors for the selective one-carbon ring expansion of N-substituted pyrroles and indoles to the corresponding pyridinium and quinolinium salts. Preliminary investigatio... Read More about Photochemically Mediated Ring Expansion of Indoles and Pyrroles with Chlorodiazirines: Synthetic Methodology and Thermal Hazard Assessment.

Coaxial Dielectric Spectroscopy as an In-Line Process Analytical Technique for Reaction Monitoring (2023)
Journal Article
Dalligos, D. M., Pilling, M. J., Dimitrakis, G., & Ball, L. T. (2023). Coaxial Dielectric Spectroscopy as an In-Line Process Analytical Technique for Reaction Monitoring. Organic Process Research and Development, 27(6), 1094-1103. https://doi.org/10.1021/acs.oprd.3c00081

The suitability of broadband dielectric spectroscopy (DS) as a tool for in-line (in situ) reaction monitoring is demonstrated. Using the esterification of 4-nitrophenol as a test-case, we show that multivariate analysis of time-resolved DS data – col... Read More about Coaxial Dielectric Spectroscopy as an In-Line Process Analytical Technique for Reaction Monitoring.

Skeletal Editing: Interconversion of Arenes and Heteroarenes (2023)
Journal Article
Joynson, B. W., & Ball, L. T. (2023). Skeletal Editing: Interconversion of Arenes and Heteroarenes. Helvetica Chimica Acta, 106(3), Article e202200182. https://doi.org/10.1002/hlca.202200182

Skeletal editing involves making specific point-changes to the core of a molecule through the selective insertion, deletion or exchange of atoms. It thus represents a potentially powerful strategy for the step-economic modification of complex substra... Read More about Skeletal Editing: Interconversion of Arenes and Heteroarenes.

meta-Selective C–H arylation of phenols via regiodiversion of electrophilic aromatic substitution (2022)
Journal Article
Senior, A., Ruffell, K., & Ball, L. T. (2022). meta-Selective C–H arylation of phenols via regiodiversion of electrophilic aromatic substitution. Nature Chemistry, https://doi.org/10.1038/s41557-022-01101-0

Electrophilic aromatic substitution is among the most widely used mechanistic manifolds in organic chemistry. Access to certain substitution patterns is, however, precluded by intrinsic and immutable substituent effects that ultimately restrict the d... Read More about meta-Selective C–H arylation of phenols via regiodiversion of electrophilic aromatic substitution.

Umpolung Synthesis of Pyridyl Ethers by Bi(V)‐Mediated O‑Arylation of Pyridones (2022)
Journal Article
Ruffell, K., Gallegos, L., Ling, K., Paton, R. S., & Ball, L. T. (2022). Umpolung Synthesis of Pyridyl Ethers by Bi(V)‐Mediated O‑Arylation of Pyridones. Angewandte Chemie International Edition, 61(51), Article e202212873. https://doi.org/10.1002/anie.202212873

We report that O-selective arylation of 2- and 4-pyridones with arylboronic acids is affected by a modular, bismacycle-based system. The utility of this umpolung approach to pyridyl ethers, which is complementary to conventional methods based on S N... Read More about Umpolung Synthesis of Pyridyl Ethers by Bi(V)‐Mediated O‑Arylation of Pyridones.

Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/SN2-Displacement of Kukhtin–Ramirez Intermediates (2022)
Journal Article
Calcatelli, A., Denton, R. M., & Ball, L. T. (2022). Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/SN2-Displacement of Kukhtin–Ramirez Intermediates. Organic Letters, https://doi.org/10.1021/acs.orglett.2c03201

We report a concise and modular approach to α,α-diaryl α-amino esters from readily available α-keto esters. This mild, one-pot protocol proceeds via ketone umpolung, with in situ formation of a Kukhtin-Ramirez intermediate preceding sequential electr... Read More about Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/SN2-Displacement of Kukhtin–Ramirez Intermediates.

Bismuth-Mediated α-Arylation of Acidic Diketones with ortho-Substituted Boronic Acids (2022)
Journal Article
Ruffell, K., Argent, S. P., Ling, K. B., & Ball, L. T. (2022). Bismuth-Mediated α-Arylation of Acidic Diketones with ortho-Substituted Boronic Acids. Angewandte Chemie International Edition, 61(40), Article e202210840. https://doi.org/10.1002/anie.202210840

The α-arylation of cyclic and fluoroalkyl 1,3-diketones is made challenging by the highly stabilized nature of the corresponding enolates, and is especially difficult for sterically demanding aryl partners. As a general solution to this problem, we r... Read More about Bismuth-Mediated α-Arylation of Acidic Diketones with ortho-Substituted Boronic Acids.

Generation of Thiyl Radicals from Air-Stable, Odorless Thiophenol Surrogates: Application to Visible-Light-Promoted C–S Cross-Coupling (2022)
Journal Article
Swan, C., Maggi, L., Park, M., Taylor, S., Shepherd, W., & Ball, L. T. (2022). Generation of Thiyl Radicals from Air-Stable, Odorless Thiophenol Surrogates: Application to Visible-Light-Promoted C–S Cross-Coupling. SYNTHESIS, 15(54), 3399-3408. https://doi.org/10.1055/s-0041-1737816

The synthetic versatility of thiophenols is offset by their air-sensitivity and foul odor. It is demonstrated that S-aryl isothiouronium salts can be used as precursors to thiyl radicals, extending the practical benefits of these air-stable, odorless... Read More about Generation of Thiyl Radicals from Air-Stable, Odorless Thiophenol Surrogates: Application to Visible-Light-Promoted C–S Cross-Coupling.

Phosphine-Catalyzed Aryne Oligomerization: Direct Access to α,ω-Bisfunctionalized Oligo(ortho-arylenes) (2021)
Journal Article
Bürger, M., Ehrhardt, N., Barber, T., Ball, L. T., Namyslo, J. C., Jones, P. G., & Werz, D. B. (2021). Phosphine-Catalyzed Aryne Oligomerization: Direct Access to α,ω-Bisfunctionalized Oligo(ortho-arylenes). Journal of the American Chemical Society, 143(40), 16796-16803. https://doi.org/10.1021/jacs.1c08689

A phosphine-catalyzed oligomerization of arynes using selenocyanates was developed. The use of JohnPhos as a bulky phosphine is the key to accessing α,ω-bisfunctionalized oligo(ortho-arylenes) with RSe as the substituent at one terminus and CN as the... Read More about Phosphine-Catalyzed Aryne Oligomerization: Direct Access to α,ω-Bisfunctionalized Oligo(ortho-arylenes).

Bismuth(V)-Mediated C–H Arylation of Phenols and Naphthols (2020)
Journal Article
Senior, A., & Ball, L. T. (2021). Bismuth(V)-Mediated C–H Arylation of Phenols and Naphthols. SYNLETT, 32(03), 235-240. https://doi.org/10.1055/s-0040-1706294

We recently reported a general and practical strategy for the Bi(V)-mediated C–H arylation of phenols and naphthols. Our telescoped protocol proceeds via transmetallation from readily available arylboronic acids to a stable Bi(III) precursor, oxidati... Read More about Bismuth(V)-Mediated C–H Arylation of Phenols and Naphthols.

Kinetic Analysis of Domino Catalysis: A Case Study on Gold-Catalyzed Arylation (2020)
Journal Article
Ball, L. T., Corrie, T., Cresswell, A., & Lloyd-Jones, G. C. (2020). Kinetic Analysis of Domino Catalysis: A Case Study on Gold-Catalyzed Arylation. ACS Catalysis, 10(18), 10420–10426. https://doi.org/10.1021/acscatal.0c03178

Domino catalysis is a well-explored route to increasing the efficiency of multistep reactions. However, the kinetic features required for efficient turnover of a process where "multiple transformations are effected by a single catalytic mechanism"hav... Read More about Kinetic Analysis of Domino Catalysis: A Case Study on Gold-Catalyzed Arylation.

Organobismuth Redox Manifolds: Versatile Tools for Synthesis (2020)
Journal Article
Ruffell, K., & Ball, L. T. (2020). Organobismuth Redox Manifolds: Versatile Tools for Synthesis. Trends in Chemistry, 2(10), 867-869. https://doi.org/10.1016/j.trechm.2020.07.008

Bismuth’s ability to manoeuvre between oxidation states supports several distinct reaction manifolds. Recent advances in the design, synthesis and application of organobismuth reagents and catalysts illustrate the potential of these redox manifolds a... Read More about Organobismuth Redox Manifolds: Versatile Tools for Synthesis.

Expanding Ligand Space: Preparation, Characterization, and Synthetic Applications of Air-Stable, Odorless Di-tert-alkylphosphine Surrogates (2020)
Journal Article
Barber, T., Argent, S. P., & Ball, L. T. (2020). Expanding Ligand Space: Preparation, Characterization, and Synthetic Applications of Air-Stable, Odorless Di-tert-alkylphosphine Surrogates. ACS Catalysis, 10, 5454-5461. https://doi.org/10.1021/acscatal.0c01414

The di-tert-alkylphosphino motif is common to many best-in-class ligands for late-transition-metal catalysis. However, the structural diversity of these privileged substructures is currently limited by the need to manipulate highly toxic, highly reac... Read More about Expanding Ligand Space: Preparation, Characterization, and Synthetic Applications of Air-Stable, Odorless Di-tert-alkylphosphine Surrogates.

Polyurethanes and Polyallophanates via Sequence-Selective Copolymerization of Epoxides and Isocyanates (2020)
Journal Article
Jurrat, M., Pointer-Gleadhill, B. J., Ball, L. T., Chapman, A., & Adriaenssens, L. (2020). Polyurethanes and Polyallophanates via Sequence-Selective Copolymerization of Epoxides and Isocyanates. Journal of the American Chemical Society, 142(18), 8136-8141. https://doi.org/10.1021/jacs.0c03520

Aryl isocyanates are introduced as comonomers for ring-opening copolymerization (ROCOP) with epoxides. Informed by studies of reaction kinetics, we show that divergent sequence selectivity for AB- and ABB-type copolymers can be achieved with a single... Read More about Polyurethanes and Polyallophanates via Sequence-Selective Copolymerization of Epoxides and Isocyanates.