Yang Zheng, Hao Wen-Juan, Wang Shu-Liang, Zhang Jin-Peng, Jiang Bo, Li Guigen, Tu Shu-Jiang
School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou, Jiangsu, 221116, People's Republic of China.
Department of Public Health, Xuzhou Medical College , Xuzhou, Jiangsu 221000, People's Republic of China.
J Org Chem. 2015 Sep 18;80(18):9224-30. doi: 10.1021/acs.joc.5b01684. Epub 2015 Aug 27.
A new TBHP/TBAI-mediated reaction of propargyl alcohols with sulfonyl hydrazides in the presence of HOAc has been established, in which a wide variety of allenyl sulfones were obtained in moderate to excellent yields. Mechanistic studies indicate that this transformation involves HOAc-promoted sulfonohydrazide intermediate formation, sequential C-O, C-N, and N-S bond cleavage, and C-S bond formation. Significantly, this sulfonohylation proceeds in a radical process and shows highly functional group compatibility and excellent regioselectivity, with a short reaction time and inexpensive reagents.
已建立了一种在醋酸存在下，叔丁基过氧化氢/四丁基碘化铵介导的炔丙醇与磺酰肼的新反应，该反应能以中等至优异的产率得到多种烯丙基砜。机理研究表明，这种转化涉及醋酸促进的磺酰肼中间体形成、依次的碳-氧、碳-氮和氮-硫键断裂以及碳-硫键形成。值得注意的是，这种磺酰化反应以自由基过程进行，具有高度的官能团兼容性和优异的区域选择性，反应时间短且试剂廉价。
