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Bedford-Type Palladacycle-Catalyzed Miyaura Borylation of Aryl Halides with Tetrahydroxydiboron in Water
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