Ion-Pair-Directed meta -Selective C-H Borylation of Aromatic Quaternary Ammonium Salts
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Peer-reviewed
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Authors
Mihai, MT
Phipps, RJ
Abstract
We recently reported the use of ion pairing as a key noncovalent interaction to control regioselectivity in the iridium-catalyzed C–H borylation of aromatic quaternary ammonium salts. Two classes of substrates, benzylamine- and aniline-derived ammonium salts were selectively borylated at the meta position by employing a newly developed anionic ligand for the iridium. It was proposed that the ligand interacts with the cationic substrate via an ion-pairing interaction, positioning the substrate in the optimal orientation for selective activation of the
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Keywords
ion pairing, iridium, borylation, meta selectivity, C-H activation
Journal Title
Synlett
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Journal ISSN
0936-5214
1437-2096
1437-2096
Volume Title
28
Publisher
Georg Thieme Verlag KG
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Sponsorship
The Royal Society (uf130004)
Engineering and Physical Sciences Research Council (EP/N005422/1)
Engineering and Physical Sciences Research Council (EP/N005422/1)
We are grateful to AstraZeneca for a studentship (M.T.M.) through the AZ-Cambridge PhD Program and the Royal Society for a University Research Fellowship (R.J.P.).