Trapping of Arynes with In Situ Generated Aryltrifluoromethylnitrones Enables Access to Trifluoromethylated Benzoxazolines

Herein, we report a rare example of trapping arynes using in situ generated aryltrifluoromethylnitrone to access an important class of trifluoromethylated benzoxazolines. This three-component strategy involves a nitrone formation/[3 + 2] cycloaddition/thermal rearrangement cascade and furnishes trif...

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Bibliographic Details
Published in:Organic letters 2023-10, Vol.25 (41), p.7551-7556
Main Authors: Jamali, Muhammad Fahad, Ahmad, Mumtaz, Chandrasekharan, Sanoop P., Mohanan, Kishor
Format: Article
Language:English
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Summary:Herein, we report a rare example of trapping arynes using in situ generated aryltrifluoromethylnitrone to access an important class of trifluoromethylated benzoxazolines. This three-component strategy involves a nitrone formation/[3 + 2] cycloaddition/thermal rearrangement cascade and furnishes trifluoromethylated benzoxazolines in high yields. The scope of the reaction is quite broad with respect to aryltrifluorodiazoethanes, nitrosoarenes, and arynes. The proposed reaction pathway is supported through the isolation and characterization of the key reaction intermediates phenyltrifluoromethylnitrone and benzisoxazoline.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02895