Ag-Catalyzed Annulation of o‑Alkynylaryl Aldehydes, Amines, and Diazo Compounds: Construction of Trifluoromethyl- and Cyano-Functionalized Benzo[d]azepines

Ag-Catalyzed Annulation of o‑Alkynylaryl Aldehydes, Amines, and Diazo Compounds: Construction of Trifluoromethyl- and Cyano-Functionalized Benzo[d]azepines

A Ag-catalyzed three-component annulation protocol, which uses o-alkynylaryl aldehydes, amines, and trifluorodiazoethane or diazoacetonitrile, to forge a new class of trifluoromethyl- and cyano-functionalized benzo­[d]­azepine is presented in this Letter. The key transformations involved in this rea...

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Veröffentlicht in:Organic letters 2023-08, Vol.25 (31), p.5806-5811
Hauptverfasser: Chandrasekharan, Sanoop P., Dhami, Anamika, Mohanan, Kishor
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container_issue 31
container_start_page 5806
container_title Organic letters
container_volume 25
creator Chandrasekharan, Sanoop P.
Dhami, Anamika
Mohanan, Kishor
description A Ag-catalyzed three-component annulation protocol, which uses o-alkynylaryl aldehydes, amines, and trifluorodiazoethane or diazoacetonitrile, to forge a new class of trifluoromethyl- and cyano-functionalized benzo­[d]­azepine is presented in this Letter. The key transformations involved in this reaction are the transient formation of the isoquinolinium intermediate and the subsequent ring-expansive addition of in situ-formed silver trifluorodiazoethylide to this intermediate. The practicality of this protocol is illustrated by realizing access to a wide range of densely functionalized benzo­[d]­azepines.
doi_str_mv 10.1021/acs.orglett.3c02053
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title Ag-Catalyzed Annulation of o‑Alkynylaryl Aldehydes, Amines, and Diazo Compounds: Construction of Trifluoromethyl- and Cyano-Functionalized Benzo[d]azepines
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