3 years ago

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

Bedford-Type Palladacycle-Catalyzed Miyaura Borylation
of Aryl Halides with Tetrahydroxydiboron in Water
Dinesh N. Sawant, Weiyuan Du, Arwa A. Makki, Anna Zernickel, Nagaiyan Sekar, Jörg Eppinger, Seema A. Ghorpade
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02771

DOI: 10.1021/acs.joc.7b02771

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