Cobalt-catalysed acyl silane directed ortho C–H functionalisation of benzoyl silanes

Despite their synthetic utility, practical methods to prepare diversely functionalized aromatic acyl silanes (benzoyl silanes) remain scarce. We herein report that cobalt complexes can successfully engage acyl silanes as weakly coordinating directing groups to catalyse the ortho C–H functionalisatio...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-11, Vol.58 (90), p.12604-12607
Main Authors: Atkin, Liselle, Priebbenow, Daniel L.
Format: Article
Language:English
Subjects:
Alkynes
Catalysis
Chemical reactions
Cobalt compounds
Silanes
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Summary:Despite their synthetic utility, practical methods to prepare diversely functionalized aromatic acyl silanes (benzoyl silanes) remain scarce. We herein report that cobalt complexes can successfully engage acyl silanes as weakly coordinating directing groups to catalyse the ortho C–H functionalisation of benzoyl silanes. Under Cp*Co( iii ) catalysis, installation of allyl or amido functionality at the 2-position of benzoyl silanes was achieved, while reaction with internal alkynes led to a desilylative annulation to afford indenone scaffolds. A Co( ii )/dppp catalytic system was also investigated to achieve the acyl silane directed hydroarylative cyclisation of 1,6-enynes to access unique benzoyl silane derivatives.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc05350k