jo7b02595_si_003.cif (504.75 kB)

Allylic C–S Bond Construction through Metal-Free Direct Nitroalkene Sulfonation

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posted on 22.01.2018 by Xue Lei, Lei Zheng, Chuanxin Zhang, Xiaodong Shi, Yunfeng Chen
A metal-free, open-flask protocol was developed for the preparation of allylic sulfones through direct condensation of sodium arylsulfinates and β,β-disubstituted nitroalkenes. The key step of this process was the Lewis base-promoted equilibrium between nitroalkenes and allylic nitro compounds. Through this process, the readily available conjugated nitroalkenes can be easily converted into allylic nitro compounds, which contain more reactive CC bonds toward the sulfonyl radical addition. As a result, allylic sulfones were prepared in excellent yields with a broad substrate scope under mild conditions.