Regioselective Thiol-yne Reaction of Thiol with ((Methyl-d<sub>3</sub>)sulfonyl)ethyne: Synthesis of (2-((Methyl-d<sub>3</sub>)sulfonyl)vinyl)sulfides
作者:Ji-Min Cao、Xin-Yu Liu、Weidong Rao、Shu-Su Shen、Daopeng Sheng、Shun-Yi Wang
DOI:10.1021/acs.joc.3c02100
日期:2024.1.5
Herein, we have developed a new method for the synthesis of ((methyl-d3)sulfonyl)ethyne, which is cost-effective and environmentally friendly and can be synthesized at the gram level. As an ideal thiol-yne reagent, it can be reacted with various types of thiols to afford (Z)- and (E)-type vinyl sulfides under different conditions with high selectivity. In addition, it can complete the conformational
在此,我们开发了一种合成((甲基-d 3 )磺酰基)乙炔的新方法,该方法经济有效且环境友好,并且可以在克级合成。作为一种理想的硫醇炔试剂,它可以与各种类型的硫醇在不同条件下高选择性地反应生成( Z )型和( E )型乙烯基硫醚。此外,它可以在合适的条件下完成Z型到E型产品的构象转变,并且还可以顺利进行进一步的衍生化。所有产品的氘含量均大于99%。初步的机理研究支持了可见光介导的自由基过程,为直接引入氘代甲基提供了一种新颖有效的合成策略,丰富了含C-S键化合物的构建方法。
Challenger et al., Journal of the Chemical Society, 1953, p. 292,304