Wang Dan, Du Jing, Lin Wan-Li, Li Yue-Sheng, Dong Zhi-Bing
School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, China.
Hubei Key Laboratory of Radiation Chemistry and Functional Materials, School of Nuclear Technology and Chemistry & Biology, Hubei University of Science and Technology, Xianning 437100, China.
J Org Chem. 2023 Dec 15;88(24):16906-16914. doi: 10.1021/acs.joc.3c01730. Epub 2023 Nov 29.
A stereoselective and environmentally friendly thiolation of terminal alkynes was reported. Thiuram disulfide reagents (tetramethylthiuram disulfide and tetraethylthiuram disulfide) that reacted with alkynes in dimethyl sulfoxide (DMSO)/HO could give ()-vinyl sulfides in good yields (up to 88%). This protocol features broad substrate scope, good stereoselectivity, high atom economy, good yields, and is transition metal-free. Mechanistic studies revealed that water and DMSO served as hydrogen sources, which greatly highlighted the unique reactivity of this special reaction involving two H-atom donors.
报道了一种立体选择性且环境友好的末端炔烃硫醇化反应。二硫化秋兰姆试剂（四甲基二硫化秋兰姆和四乙基二硫化秋兰姆）在二甲基亚砜（DMSO）/水体系中与炔烃反应，能够以良好的产率（高达88%）得到（）-乙烯基硫醚。该方法具有底物范围广、立体选择性好、原子经济性高以及产率良好等特点，且无需过渡金属。机理研究表明，水和DMSO作为氢源，这极大地突出了这种涉及两个氢原子供体的特殊反应的独特反应活性。
