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    Bedford-type palladacycle catalyzed Miyaura-borylation of aryl halides with tetrahydroxydiboron in water

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    Type
    Article
    Authors
    Zernickel, Anna cc
    du, weiyuan cc
    Ghorpade, Seema
    Sawant, Dinesh
    Makki, Arwa cc
    Sekar, Nagaiyan
    Eppinger, Jörg cc
    KAUST Department
    Biological & Organometallic Catalysis Laboratories
    Biological 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/2010/07
    Date
    2018-01-30
    Online Publication Date
    2018-01-30
    Print Publication Date
    2018-02-16
    Permanent link to this record
    http://hdl.handle.net/10754/626747
    
    Metadata
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    Abstract
    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 Chemistry
    DOI
    10.1021/acs.joc.7b02771
    Additional Links
    http://pubs.acs.org/doi/10.1021/acs.joc.7b02771
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.joc.7b02771
    Scopus Count
    Collections
    Articles; Biological and Environmental Sciences and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; Chemical Engineering Program; KAUST Catalysis Center (KCC); KAUST Solar Center (KSC)

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