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    Manganese-Catalyzed Regioselective Dehydrogenative C- versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation

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    Name:
    Manuscript_accepted. Maganese.pdf
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    804.9Kb
    Format:
    PDF
    Description:
    Accepted manuscript
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    Type
    Article
    Authors
    Borghs, Jannik C.
    Zubar, Viktoriia
    Azofra Mesa, Luis cc
    Sklyaruk, Jan
    Rueping, Magnus cc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2020-05-13
    Online Publication Date
    2020-05-13
    Print Publication Date
    2020-06-05
    Embargo End Date
    2021-05-13
    Submitted Date
    2020-04-10
    Permanent link to this record
    http://hdl.handle.net/10754/662838
    
    Metadata
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    Abstract
    The first base metal-catalyzed regioselective dehydrogenative alkylation of indolines using readily available alcohols as the alkylating reagent is reported. A single air- and moisture-stable manganese catalyst provides access to either C3- or N-alkylated indoles depending on the solvent used. Mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation and hydrogen autotransfer strategy.
    Citation
    Borghs, J. C., Zubar, V., Azofra, L. M., Sklyaruk, J., & Rueping, M. (2020). Manganese-Catalyzed Regioselective Dehydrogenative C- versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation. Organic Letters. doi:10.1021/acs.orglett.0c01270
    Sponsors
    This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (FCC/1/1974). We thank KAUST Supercomputing Laboratory for use of the supercomputer Shaheen II and providing the computational resources.
    Publisher
    American Chemical Society (ACS)
    Journal
    Organic Letters
    DOI
    10.1021/acs.orglett.0c01270
    PubMed ID
    32401525
    Additional Links
    https://pubs.acs.org/doi/10.1021/acs.orglett.0c01270
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.orglett.0c01270
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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