Zuo Hang-Dong, Hao Wen-Juan, Zhu Chi-Fan, Guo Cheng, Tu Shu-Jiang, Jiang Bo
School of Chemistry & Materials Science, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China.
College of Chemistry and Molecular Engineering and Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 210009, Jiangsu P. R. China.
Org Lett. 2020 Jun 5;22(11):4471-4477. doi: 10.1021/acs.orglett.0c01470. Epub 2020 May 13.
A new electrochemical three-component annulation-iodosulfonylation of 1,5-enyne-containing -quinone methides (-QMs) has been established by using available arylsulfonyl hydrazides and potassium iodide under environmentally benign conditions. The electrosynthesis offers sustainable and efficient access to construct spirocyclohexadienone-containing ()-indenes without any additional catalyst or oxidant through a sulfonyl-radical-triggered 1,6-addition and an I-mediated -cyclization cascade. Notably, potassium iodide plays the triple role of an electrolyte, a redox catalyst, as well as an iodination reagent.
在环境友好的条件下,通过使用市售的芳基磺酰肼和碘化钾,建立了一种新的含1,5-烯炔的醌甲基化物(-QMs)的电化学三组分环化-碘磺酰化反应。该电合成方法提供了一种可持续且高效的途径,通过磺酰基自由基引发的1,6-加成和碘介导的环化串联反应,无需任何额外的催化剂或氧化剂即可构建含螺环己二烯酮的()-茚。值得注意的是,碘化钾起到了电解质、氧化还原催化剂以及碘化试剂的三重作用。