Song Zhi-Jie, Bao Yu, Sun Yun-Jia, Yan Shenghu, Zhang Yue, Li Guigen, Wang Jia-Yin
School of Pharmacy, Continuous Flow Engineering Laboratory of National Petroleum and Chemical Industry, Changzhou University, Changzhou, Jiangsu 213164, China.
Jiangsu CheeShine Performance Materials Company with Limited Liability, Huaian, Jiangsu 223001, China.
J Org Chem. 2024 Apr 5;89(7):4877-4887. doi: 10.1021/acs.joc.4c00052. Epub 2024 Mar 8.
General and convenient visible-light-promoted alkylsulfonylation and cyanoalkylsulfonylation of MBH adducts have been developed through the multicomponent insertion of sulfur dioxide, enabling the assembly of two C-S bonds to generate structurally diverse allylic alkylsulfones (43 examples in total). The reaction of MBH adducts with potassium alkyltrifluoroborates and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct afforded sulfones with generally good yields. Notably, the addition of ,,','-tetramethylethylenediamine as a base into the photocatalytic system led to yielding an alkyl sulfonyl unit and cyano group-anchored trisubstituted alkenes by utilizing cycloketone oxime esters as C-radical precursors. Both of these reactions have constructed two C-S bonds, and all desired products were obtained in moderate to excellent yields with complete stereospecificity.
通过二氧化硫的多组分插入反应，开发了通用且便捷的可见光促进的MBH加合物的烷基磺酰化和氰基烷基磺酰化反应，实现了两个C-S键的构建，从而生成结构多样的烯丙基烷基砜（共43个实例）。MBH加合物与烷基三氟硼酸钾和1,4-二氮杂双环[2.2.2]辛烷双（二氧化硫）加合物的反应通常能以良好的产率得到砜。值得注意的是，在光催化体系中加入作为碱的N,N,N',N'-四甲基乙二胺，利用环酮肟酯作为C-自由基前体，可生成烷基磺酰基单元和氰基锚定的三取代烯烃。这两种反应都构建了两个C-S键，所有所需产物均以中等至优异的产率获得，且具有完全的立体专一性。
