Substrate-controlled product divergence in the reaction of α-fluoro-β-ketoamides with arynes

An interesting substrate-controlled reactivity switch has been observed in the reaction of α-fluoro-β-ketoamides with arynes. The reaction of secondary α-fluoro-β-ketoamides with arynes provided access to α-aryl-α-fluoroacetamides through an arylation/deacylation sequence. Interestingly, the reactio...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-11, Vol.58 (93), p.12987-1299
Main Authors: Chandrasekharan, Sanoop P, Vaishanv, Narendra Kumar, Kant, Ruchir, Mohanan, Kishor
Format: Article
Language:English
Subjects:
Aromatic compounds
Substrates
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Summary:An interesting substrate-controlled reactivity switch has been observed in the reaction of α-fluoro-β-ketoamides with arynes. The reaction of secondary α-fluoro-β-ketoamides with arynes provided access to α-aryl-α-fluoroacetamides through an arylation/deacylation sequence. Interestingly, the reaction of tertiary α-fluoro-β-ketoamides resulted in the C-C σ-bond insertion reaction to afford 1,2-disubstituted arenes. An interesting substrate-controlled reactivity switch has been observed in the reaction of α-fluoro-β-ketoamides with arynes leading to the synthesis of two types of α-aryl-α-fluoroacetamides.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc04657a