Liu Qing-Song, Qiu Wen-Jie, Niu Chuang, Wang Guan-Wu
Hefei National Research Center for Physical Sciences at the Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China.
J Org Chem. 2022 Dec 2;87(23):15754-15761. doi: 10.1021/acs.joc.2c01525. Epub 2022 Nov 15.
A novel and efficient palladium-catalyzed C-H activation reaction of [60]fullerene with arylphosphinic acids has been developed for the synthesis of [60]fullerene-fused phosphinolactones. A possible reaction mechanism is proposed to explain the generation of the obtained products. A representative product can be further electrochemically transformed into bis-benzylated 1,2- and 1,4-adducts of [60]fullerene. In addition, a [60]fullerene-fused phosphinolactone with a 12-membered ring can also be synthesized from the electrochemical ring expansion of the employed phosphinolactone with a 6-memebered ring with 1,2-bis(bromomethyl)benzene.
已开发出一种新颖且高效的钯催化[60]富勒烯与芳基次膦酸的C-H活化反应，用于合成[60]富勒烯稠合的膦内酯。提出了一种可能的反应机理来解释所得产物的生成。一种代表性产物可进一步电化学转化为[60]富勒烯的双苄基化1,2-和1,4-加合物。此外，具有12元环的[60]富勒烯稠合膦内酯也可通过所使用的具有6元环的膦内酯与1,2-双（溴甲基）苯的电化学扩环反应合成。
