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- Title
Remote Editing of Stacked Aromatic Assemblies for Heteroannular C−H Functionalization by a Palladium Switch between Aromatic Rings.
- Authors
Yu, Zhiqian; Liu, Qianhui; Li, Qian; Huang, Zhenmei; Yang, Yudong; You, Jingsong
- Abstract
An approach allowing remote editing of stacked aromatic assemblies for heteroannular C−H functionalization would represent a transformative chemical toolbox that may make the diversification of complex molecules in a straightforward manner. However, such a C−H activation is usually less kinetically and thermodynamically favorable than homoannular ortho C−H activation and remains a fundamental challenge. Herein we disclose an engineer's approach, using a transient ligand as an interim bridge between two aryl rings (analogues to mountaintops) to anchor the metal center on the remote heteroannular C−H bond. As a proof‐of‐concept, we present the palladium‐catalyzed heteroannular C−H olefination of stacked aromatic assemblies with olefins and allylation with vinyl acetates using L‐tert‐leucine acid as a transient ligand. Mechanistic investigations suggest an unusual olefin coordination‐promoted interannular palladium migration process determinative for reversal of the site‐selectivity.
- Subjects
PALLADIUM; ENGINEERS; ALKENES; ALLYLATION; VINYL acetate
- Publication
Angewandte Chemie, 2022, Vol 134, Issue 48, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202212079