Chen Pu, Tian Lin, Ji Xiaochen, Deng Guo-Jun, Huang Huawen
Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105, China.
School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China.
Org Lett. 2024 Apr 19;26(15):2939-2944. doi: 10.1021/acs.orglett.4c00454. Epub 2024 Apr 11.
A selective three-component 1,2-sulfonyl etherification of aryl 1,3-dienes enabled by copper catalysis to afford biologically interesting alkenyl 1,2-sulfone ether derivatives through C-S and C-O bond formation is described. The protocol proceeds with the sulfonyl chloride and alcohols under simple, mild, and base-free conditions, providing a straightforward route to sulfonylated allyl ether compounds with broad functional group tolerance and excellent chemo- and regioselectivity. Mechanistic studies indicate that the selective alkene difunctionalization includes a key copper-mediated single-electron transfer process.
描述了一种通过铜催化实现的芳基1,3 - 二烯的选择性三组分1,2 - 磺酰基醚化反应，该反应通过形成C - S和C - O键得到具有生物学意义的烯基1,2 - 砜醚衍生物。该方法在简单、温和且无碱的条件下，使用磺酰氯和醇进行反应，为具有广泛官能团耐受性以及优异化学和区域选择性的磺酰化烯丙基醚化合物提供了一条直接的合成路线。机理研究表明，选择性烯烃双官能化包括一个关键的铜介导的单电子转移过程。
