Iridium‐Catalysed C−H Borylation of Fluoroarenes: Insights into the Balance between Steric and Electronic Control of Regioselectivity
Ding, Mingyan; Reuven, Jonathan A.; Hones, Andrew C.; Fox, Mark A.; Steel, Patrick G.
Jonathan A. Reuven
Andrew C. Hones
Dr Mark Fox email@example.com
Professor Patrick Steel firstname.lastname@example.org
The iridium catalysed C−H borylation of polyfluorinated arenes and heteroarenes occurs rapidly and efficiently. As with other borylation reactions, whilst steric parameters dominate, an underlying electronic influence on reaction selectivity can be observed. Notably borylation regioselectivity in fluorinated (hetero)arenes is determined by purely electronic effects except for ortho-borylation between two fluorine atoms where steric effects of fluorine substituents become apparent. Borylation at the para position with respect to fluorine is disfavoured whereas a strong electronic preference for borylation para to the azinyl nitrogen of pyridine is observed. When these features co-operate high selectivity can be expected. For these reactions, computations based on transition state, rather than intermediate, energies in iridium geometries showed excellent agreement between predicted and observed selectivities.
Ding, M., Reuven, J. A., Hones, A. C., Fox, M. A., & Steel, P. G. (2022). Iridium‐Catalysed C−H Borylation of Fluoroarenes: Insights into the Balance between Steric and Electronic Control of Regioselectivity. European Journal of Organic Chemistry, 2022(47), https://doi.org/10.1002/ejoc.202201005
|Journal Article Type||Article|
|Online Publication Date||Dec 16, 2022|
|Deposit Date||Dec 16, 2022|
|Publicly Available Date||Dec 16, 2022|
|Journal||European Journal of Organic Chemistry|
|Peer Reviewed||Peer Reviewed|
Published Journal Article
Publisher Licence URL
© 2022 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH<br /> <br /> This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
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