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Metal-free and selective cleavage of unstrained carbon–carbon single bonds: Synthesis of β-ketosulfones from β-chlorohydrins and sodium sulfinates
Version 2 2017-10-16, 13:40
Version 1 2017-08-21, 18:55
journal contribution
posted on 2017-10-16, 13:40 authored by Yanni Li, Deqiang Liang, Yu Chang, Xiangguang Li, Shaoguang Fu, Yunli Yuan, Baoling WangA metal-free protocol for the selective cleavage of unstrained C–C single bonds was developed. Under the catalysis of KI and in the presence of NaHCO3, the readily available α-chloro-β-hydroxy ketones underwent bond breaking and sulfonylation smoothly to afford β-ketosulfones with high efficiency and broad substrate scope. Mechanism investigations, both experimental and theoretical, showed that a retro-aldol cleavage/nucleophilic substitution sequence might be involved.