Merging Cu-catalysed C-H functionalisation and intramolecular annulations: computational and experimental studies on an expedient construction of complex fused heterocycles

HAMILTON, Alexander, WOTTON, Timothy, PORTER, Jack, GREWAL, Karmjit, CHIRILA, Paula, FORBES, Sarah, COLES, Simon, HORTON, Peter and WHITEOAK, Christopher (2020). Merging Cu-catalysed C-H functionalisation and intramolecular annulations: computational and experimental studies on an expedient construction of complex fused heterocycles. Organic Chemistry Frontiers.

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Link to published version:: https://doi.org/10.1039/D0QO00283F
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    Abstract

    Intramolecular reactions provide a unique and easy opportunity to access complex heterocyclic compounds with higher complexity than intermolecular conversions. This report details how, previously unknown fused dihydrobenzofuran-isoquinolone compounds, exhibiting an unusually strained shared aromatic unit, can be readily obtained from simply prepared benzamide derivatives bearing a tethered alkyne moiety, using copper C-H bond functionalisation catalysis. The mechanism has been proposed based on detailed DFT and topological analysis studies, and shows that the two key heterocycles are formed during distinct mechanistic steps; the dihydrobenzofuran arises from a migratory insertion and the isoquinolone from the following reductive elimination, resulting in an efficient Double Annulation Reaction (DAR). Actually, the results present an unprecedented migratory insertion of alkynes with benzamides when using copper as catalyst with the 8-aminoquinoline directing group and also study why the intermolecular variant is not operative.

    Item Type: Article
    Uncontrolled Keywords: 0305 Organic Chemistry
    Identification Number: https://doi.org/10.1039/D0QO00283F
    SWORD Depositor: Symplectic Elements
    Depositing User: Symplectic Elements
    Date Deposited: 31 Mar 2020 16:24
    Last Modified: 31 Mar 2020 16:24
    URI: http://shura.shu.ac.uk/id/eprint/26087

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