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

Xue Lei, Lei Zheng, Chuanxin Zhang, Xiaodong Shi* and Yunfeng Chen*

*University of South Florida, 4202 E. Fowler Avenue, Tampa, Florida 33620, United States; Wuhan Institute of Technology, Wuhan 430073, P. R. China, Email: xmshiusf.edu, yfchenwit.edu.cn

X. Lei, L. Zheng, C. Zhang, X. Shi, Y. Chen, J. Org. Chem., 2018, 83, 1772-1778.

DOI: 10.1021/acs.joc.7b02595 (free Supporting Information)


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Abstract

A metal-free direct condensation of sodium arylsulfinates and β,β-disubstituted nitroalkenes provides allylic sulfones in excellent yields with a broad substrate scope under mild conditions. The key step of this process was a Lewis base-promoted equilibrium between nitroalkenes and allylic nitro compounds, which contain more reactive C=C bonds toward sulfonyl radical addition.

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proposed reaction mechanism



Key Words

allylic sulfones, TBHP


ID: J42-Y2018