meta-Selective C−H Borylation of Benzylamine-, Phenethylamine-, and Phenylpropylamine-Derived Amides Enabled by a Single Anionic Ligand
Angewandte Chemie - International Edition
John Wiley & Sons Ltd.
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Davis, H., Genov, G., & Phipps, R. (2017). meta-Selective C−H Borylation of Benzylamine-, Phenethylamine-, and Phenylpropylamine-Derived Amides Enabled by a Single Anionic Ligand. Angewandte Chemie - International Edition, 129 (43), 13536-13540. https://doi.org/10.1002/ange.201708967
Selective functionalization at the meta position of arenes remains a significant challenge. In this work, we demonstrate that a single anionic bipyridine ligand bearing a remote sulfonate group enables selective iridium-catalyzed borylation of a range of common amine-containing aromatic molecules at the arene meta position. We propose that this selectivity is the result of a key hydrogen bonding interaction between the substrate and catalyst. The scope of this meta-selective borylation is demonstrated on amides derived from benzylamines, phenethylamines and phenylpropylamines; amine-containing building blocks of great utility in many applications.
C-H-Aktivierung, Homogene Katalyse, Nichtkovalente Wechselwirkungen, Regioselektivität, Wasserstoffbrücken
We are grateful to the EPSRC and Pfizer for a CASE studentship (H.J.D.), the EPSRC (EP/N005422/1, G.R.G.) and the Royal Society for a University Research Fellowship (R.J.P.).
Royal Society (uf130004)
External DOI: https://doi.org/10.1002/ange.201708967
This record's URL: https://www.repository.cam.ac.uk/handle/1810/268067
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