Sun Xiang, Ma Hong-Xing, Mei Tian-Sheng, Fang Ping, Hu Yulai
College of Chemistry and Chemical Engineering , Northwest Normal University , 967 Anning East Road , Lanzhou 730070 , China.
State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , China.
Org Lett. 2019 May 3;21(9):3167-3171. doi: 10.1021/acs.orglett.9b00867. Epub 2019 Apr 17.
Given the versatility and value of the structurally diverse organohalides and CF-containing compounds in organic synthesis, we reported a green, oxidant-free electrochemical method using undivided electrochemical cells for radical bromination, chlorination and trifluoromethylation-formyloxylation of the various alkenes with readily available halogen radical (NaCl, NaBr), trifluoromethyl radical (CFSONa) sources, and DMF as formyloxylation reagents. The protocol is operationally simple and robust and the Cl, Br or CF was directly oxidized at the anode, obviating the need for exogenous chemical oxidants.
鉴于结构多样的有机卤化物和含氟化合物在有机合成中的多功能性和价值，我们报道了一种绿色、无氧化剂的电化学方法，该方法使用未分隔的电化学电池，以易于获得的卤素自由基（氯化钠、溴化钠）、三氟甲基自由基（三氟甲磺酸钠）源以及作为甲酰氧基化试剂的N,N-二甲基甲酰胺，对各种烯烃进行自由基溴化、氯化和三氟甲基化-甲酰氧基化反应。该方案操作简单且稳定，氯、溴或三氟甲基在阳极直接被氧化，无需外源化学氧化剂。
