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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.