Abstract
Direct β-arylation of thiophene derivatives with bromide as directing group is disclosed. The reaction is conducted with PdCl2/(p-tolyl)3P as catalyst, silver carbonate as additive, and aryl iodide as coupling partner, affording brominated biaryl compounds as product. Control experiments indicated that the presence of bromide group enhances the reactivity of the C-H bond, enabling β-arylation. Furthermore, the C-Br bond can be easily converted into many useful functional groups through a wide range of methodologies. The mechanistic study suggests that silver salt plays a key role in the C-H bond-activation step.
| Original language | English |
|---|---|
| Pages (from-to) | 4025-4032 |
| Number of pages | 8 |
| Journal | Synthesis (Germany) |
| Volume | 54 |
| Issue number | 18 |
| DOIs | |
| State | Published - Aug 21 2022 |
| Externally published | Yes |
Funding
Part of this work was conducted at Center for Nanophase Materials Sciences, which is a DOE Office of Science User Facility. Dr. Hong-Hai Zhang is currently supported by the Center for Structural Molecular Biology, sponsored by the office of Biological and Environmental Research. Dr. Kunlun Hong is supported by the Center for Nanophase Materials Sciences, which is a DOE Office of Science User Facility. This research was started by Hong-Hai Zhang as professor at Nanjing Tech University.
Keywords
- bromide
- silver
- thiophene
- β-arylation