期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 4, 页码 1842-1851出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02771
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资金
- King Abdullah University of Science and Technology (KAUST)
- King Abdullah University of Science and Technology (GCR grant) [FIC/2010/07]
- King Abdullah University of Science and Technology (KAUST), Saudi Arabia
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 degrees C in short time of 6 h 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.
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