meta-Selective C−H Borylation of Benzylamine-, Phenethylamine-, and Phenylpropylamine-Derived Amides Enabled by a Single Anionic Ligand
Published version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
Davis, HJ
Genov, GR
Phipps, RJ
Abstract
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.
Description
Keywords
C-H-Aktivierung, Homogene Katalyse, Nichtkovalente Wechselwirkungen, Regioselektivität, Wasserstoffbrücken
Journal Title
Angewandte Chemie - International Edition
Conference Name
Journal ISSN
1433-7851
1521-3773
1521-3773
Volume Title
129
Publisher
John Wiley & Sons Ltd.
Publisher DOI
Sponsorship
Engineering and Physical Sciences Research Council (EP/N005422/1)
The Royal Society (uf130004)
EPSRC (1502977)
Engineering and Physical Sciences Research Council (EP/K039520/1)
The Royal Society (uf130004)
EPSRC (1502977)
Engineering and Physical Sciences Research Council (EP/K039520/1)
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.).