New Strategies for the Arylation of Weak Nucleophiles
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New Strategies for the Arylation of Weak Nucleophiles
Wed, 19/03/2025 - 14:00 to 15:00
Location:
Speaker:
Prof. Liam Ball
Affiliation:
University of Nottingham
Synopsis:
The catalytic cross-coupling of C-, N- and O-nucleophiles is an essential tool for the pharmaceutical and agrochemical industries. However, despite the highly sophisticated state of the art, the arylation of weak nucleophiles remains challenging due to the low rate of reductive elimination from highly polarized M−R bonds. We have developed a suite of methods for the electrophilic arylation of weak nucleophiles with non-toxic Bi(V) reagents. This methodology relies on in situ generation of a reactive Bi(V) arylating agent from a bench-stable Bi(III) precursor via telescoped B-to-Bi transmetallation and oxidation. Insight from experimental and computational mechanistic studies has revealed the key role that the identity of the Bi(V) intermediate plays in controlling reactivity and selectivity, ultimately allowing extension of our methodology from the ortho-selective arylation of phenols1 to O-H,2 C(sp3)-H3 and meta-selective4 arylation.
References:
1. Jurrat, M.; Maggi, L.; Lewis, W.; Ball, L. T. Nature Chem. 2020, 12, 260.
2. Ruffell, K.; Gallegos, L. C.; Ling, K. B.; Paton, R. S.; Ball, L. T. Angew. Chem. Int. Ed. 2022, 61, e202212873.
3. Ruffell, K.; Argent, S. P.; Ling, K. B.; Ball, L. T. Angew. Chem. Int. Ed. 2022, 61, e202210840.
4. Senior, A.; Ruffell, K.; Ball, L. T. Nature Chem. 2023, 15, 386.
Biography:
Liam Ball completed his Master’s degree at the University of Bristol in 2009. He obtained his PhD from the same institution in 2014 under the supervision of Dr Chris Russell and Professor Guy Lloyd-Jones FRS, and moved with Prof. Lloyd-Jones to Edinburgh for postdoctoral research. Liam began his independent career at Nottingham in 2015, was promoted to Associate Professor in 2021, and to Full Professor in 2024. He currently holds a UKRI Future Leaders Fellowship, in 2024 was awarded the RSC Hickinbottom Award, the RSC-BMOS Early Career Award, the RSC Inorganic Reaction Mechanisms Early Career Award, and in 2025 was named a Laureate of the Blavatnik Awards for Young Scientists in the UK.