Abstract
A mild aqueous protocol for palladium catalyzed Miyaura borylation of aryl iodides, aryl bromides and aryl chlorides with tetrahydroxydiboron (BBA) as a borylating agent is developed. The developed methodology requires low catalyst loading of Bedford-type palladacycle catalyst (0.05 mol %) and works best under mild reaction conditions at 40 °C in short time of 6 hours in water. In addition, our studies show that for Miyaura borylation using BBA in aqueous condition, maintaining a neutral reaction pH is very important for reproducibility and higher yields of corresponding borylated products. Moreover, our protocol is applicable for a broad range of aryl halides, corresponding borylated products are obtained in excellent yields up to 93% with 29 examples demonstrating its broad utility and functional group tolerance.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1842-1851 |
| Number of pages | 10 |
| Journal | The Journal of Organic Chemistry |
| Volume | 83 |
| Issue number | 4 |
| DOIs | |
| State | Published - Jan 30 2018 |
Bibliographical note
KAUST Repository Item: Exported on 2020-10-01Acknowledged KAUST grant number(s): FIC/2010/07
Acknowledgements: This work was supported by the King Abdullah University of Science and Technology (KAUST baseline funding and GCR grant FIC/2010/07). Authors are gratefully acknowledging support from King Abdullah University of Science and Technology (KAUST), Saudi Arabia.