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Nitro-Spirocyclization of Biaryl Ynones with tert-Butyl Nitrite: Access to NO2‑Substituted Spiro[5,5]trienones

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posted on 2023-03-22, 20:04 authored by Yang Li, Lijun Li, Changyou Guo, Qinqin Yan, Hongxun Zhou, Ying Wang, Zhong-Quan Liu, Zejiang Li
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 NO2-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.

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