Nitro-Spirocyclization of Biaryl Ynones with <i>tert</i>-Butyl Nitrite: Access to NO<sub>2</sub>-Substituted Spiro[5,5]trienones
Yang Li, Li‐Jun Li, Changyou Guo, Qinqin Yan, Hongxun Zhou, Ying Wang, Zhong‐Quan Liu, Zejiang Li
Abstract
A metal/peroxide-free involved simple cascade 6- exo -trig spirocyclization of tert -butyl nitrite with biaryl ynones has been finished, which resulted in various NO 2 -modified spiro[5,5]trienones with good regioselectivity/yields. A variety of scaled-up experiments, reduction/epoxidation operations, and mechanistic studies were performed to verify the merits and spirocyclization process of this radical system. Finally, the structure of the spirocycles was confirmed by single-crystal X-ray diffraction.
Topics & Concepts
RegioselectivityNitriteNitroPeroxideChemistryCombinatorial chemistryCascadeMedicinal chemistryOrganic chemistryCatalysisNitrateChromatographyAlkylOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions