Abstract
A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C−H activator and ethylene synthon via a retro-Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
| Original language | English |
|---|---|
| Pages (from-to) | 7166-7170 |
| Number of pages | 5 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 56 |
| Issue number | 25 |
| Online published | 16 May 2017 |
| DOIs | |
| Publication status | Published - 12 Jun 2017 |
| Externally published | Yes |
Funding
We thank RGC of Hong Kong (CRF: C5023-14G, GRF: 15336716 and PolyU11/CRF/13E) for financial and X-ray equipment support; and Prof. Gavin C. Tsui (CUHK) and Prof. Man-Kit Leung (NTU, Taiwan) for helpful discussions to this manuscript.
Research Keywords
- cross-coupling
- C−H functionalization
- decarboxylation
- palladium
- polycyclic aromatic hydrocarbons
RGC Funding Information
- RGC-funded
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