Journal of Organic Chemistry p. 1842 - 1851 (2018)
Update date:2022-08-11
Topics:
Zernickel, Anna
Du, Weiyuan
Ghorpade, Seema A.
Sawant, Dinesh N.
Makki, Arwa A.
Sekar, Nagaiyan
Eppinger, J?rg
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 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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