Widely-used boronic esters as synthetically-versatile directing groups for C–H activation and hydrogen isotope exchange

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Townsley, Conor and Smith, Connor and Lindsay, David and Liwicki, Gemma M. and Measom, Nicholas D. and Paterson, Laura and Kerr, William (2026) Widely-used boronic esters as synthetically-versatile directing groups for C–H activation and hydrogen isotope exchange. Chemical Science. ISSN 2041-6539 (https://doi.org/10.1039/D5SC09113F)

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Abstract

Herein we report the first use of accessible boron-containing compounds as highly effective directing groups for C–H activation and hydrogen isotope exchange. Selective ortho-activation and functionalisation at aromatic C-sp2 centres have been achieved across an array of aryl boronic ester species using an iridium-based, NHC/phosphine catalyst system at low loadings. The process is robust, with a wide scope of over 30 substrates, and delivers excellent levels of deuterium incorporation in a selective manner. Further utilisation of the resulting boron-containing isotopologues in cross-coupling chemistry has allowed the late-stage preparation of previously less accessible site-selectively labelled structures. This strategy has been exemplified via the preparation of an isotopically-labelled, biologically-active drug molecule.

ORCID iDs

Townsley, Conor, Smith, Connor, Lindsay, David ORCID logoORCID: https://orcid.org/0000-0003-4498-5094, Liwicki, Gemma M., Measom, Nicholas D., Paterson, Laura ORCID logoORCID: https://orcid.org/0009-0006-5976-7099 and Kerr, William ORCID logoORCID: https://orcid.org/0000-0002-1332-785X;
CORE (COnnecting REpositories)