1. Dearomative Dual Functionalization of Aryl Iodanes.
- Author
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Zhao, Weizhao, Huang, Xin, Zhan, Yaling, Zhang, Qifeng, Li, Dongyang, Zhang, Yage, Kong, Lichun, and Peng, Bo
- Subjects
SIGMATROPIC rearrangements ,AROMATICITY ,NUCLEOPHILES ,ARYL group ,FUNCTIONAL groups - Abstract
Herein we describe the dearomatization of aryl iodanes through an unprecedented "rearrangement/addition" sequence. The process consists of two stages. First, a rapid [3,3] sigmatropic rearrangement of the aryl iodane with an α‐stannyl nitrile affords a highly electrophilic dearomatized intermediate at −78 °C. A low‐temperature rearrangement then enables the unstable dearomatized species to be trapped in situ with various nucleophiles. As a consequence, the reaction not only breaks the aromaticity of the aryl iodane but also sequentially installs two different functional groups, thus resulting in a polysubstituted alicyclic product. [ABSTRACT FROM AUTHOR]
- Published
- 2019
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