Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 43, Pages 13351-13355Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201708967
Keywords
C-H activation; homogeneous catalysis; hydrogen bonding; noncovalent interactions; regioselectivity
Categories
Funding
- EPSRC
- Pfizer
- EPSRC [EP/N005422/1]
- Royal Society
- EPSRC [EP/K039520/1, EP/N005422/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/N005422/1, EP/K039520/1] Funding Source: researchfish
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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.
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