All Outputs (5)

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.