Bedford-type palladacycle catalyzed Miyaura-borylation of aryl halides with tetrahydroxydiboron in water
Type
ArticleAuthors
Zernickel, Anna
du, weiyuan

Ghorpade, Seema
Sawant, Dinesh
Makki, Arwa

Sekar, Nagaiyan
Eppinger, Jörg

KAUST Department
Biological & Organometallic Catalysis LaboratoriesBiological and Environmental Sciences and Engineering (BESE) Division
Chemical Engineering Program
Chemical Science Program
KAUST Catalysis Center (KCC)
KAUST Solar Center (KSC)
Office of the VP
Physical Science and Engineering (PSE) Division
Young Talent Development
KAUST Grant Number
FIC/2010/07Date
2018-01-30Online Publication Date
2018-01-30Print Publication Date
2018-02-16Permanent link to this record
http://hdl.handle.net/10754/626747
Metadata
Show full item recordAbstract
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 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.Citation
Zernickel 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.Sponsors
This 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.Publisher
American Chemical Society (ACS)Journal
The Journal of Organic ChemistryAdditional Links
http://pubs.acs.org/doi/10.1021/acs.joc.7b02771ae974a485f413a2113503eed53cd6c53
10.1021/acs.joc.7b02771