2 + 2 + 1] Heteroannulation of Alkenes with Enynyl Benziodoxolones and Silver Nitrite Involving C≡C bond Oxidative Cleavage: Entry to 3-Aryl-Δ2-isoxazolines.

Abstract

A copper-catalyzed [2 + 2 + 1] heteroannulation of alkenes with enynyl benziodoxolones and AgNO2 involving oxidative cleavage of the C≡C bond promoted by cooperative Zn(OTf)2, KOAc, and 4 Å MS for producing 3-aryl Δ2-isoxazolines is reported. Mechanistic studies indicate that AgNO2 serves as the N/O two-atom unit source, enabling the formation of three bonds through NO2 addition across the C≡C bond, NO-transfer, C≡C bond cleavage, and annulation cascades.