Bedford-type palladacycle catalyzed Miyaura-borylation of aryl halides with tetrahydroxydiboron in water
Sawant, Dinesh Nanaji
KAUST DepartmentKAUST Solar Center (KSC)
Physical Sciences and Engineering (PSE) Division
Chemical Science Program
Biological and Environmental Sciences and Engineering (BESE) Division
Chemical and Biological Engineering Program
KAUST Catalysis Center (KCC)
KAUST Grant NumberFIC/2010/07
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AbstractA 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.
CitationZernickel A, Du W, Ghorpade S, Sawant DN, Makki AA, et al. (2018) Bedford-type palladacycle catalyzed Miyaura-borylation of aryl halides with tetrahydroxydiboron in water. The Journal of Organic Chemistry. Available: http://dx.doi.org/10.1021/acs.joc.7b02771.
SponsorsThis 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.
PublisherAmerican Chemical Society (ACS)
JournalThe Journal of Organic Chemistry