Direct Access to Trifluoromethylated Benzo[d]oxepines from o‑Alkynylaryl Aldehydes and Trifluorodiazoethane

Reported in this Letter is a silver-catalyzed reaction between o-alkynylaryl aldehydes and trifluorodiazoethane that enables an expedient synthesis of trifluoromethylated benzo­[d]­oxepines. The reaction works through a silver-promoted 6-endo-dig cyclization of o-alkynylbenzaldehydes for the generat...

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Bibliographic Details
Published in:Organic letters 2023-05, Vol.25 (17), p.3018-3022
Main Authors: Dhami, Anamika, Chandrasekharan, Sanoop P., Mohanan, Kishor
Format: Article
Language:English
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Summary:Reported in this Letter is a silver-catalyzed reaction between o-alkynylaryl aldehydes and trifluorodiazoethane that enables an expedient synthesis of trifluoromethylated benzo­[d]­oxepines. The reaction works through a silver-promoted 6-endo-dig cyclization of o-alkynylbenzaldehydes for the generation of an isochromenylium intermediate, which upon a ring-expansive addition of trifluorodiazoethane delivers a novel class of trifluoromethylated benzoxepine frameworks. This strategy was applied to the synthesis of phosphonylated benzo­[d]­oxepines using the Seyferth–Gilbert reagent.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00801