Wang Junchao, Sun Kai, Chen Xiaolan, Chen Tong, Liu Yan, Qu Lingbo, Zhao Yufen, Yu Bing
College of Chemistry and Molecular Engineering , Zhengzhou University , Zhengzhou 450001 , China.
The Key Laboratory for Chemical Biology of Fujian Province , Xiamen University , Xiamen 361005 , China.
Org Lett. 2019 Mar 15;21(6):1863-1867. doi: 10.1021/acs.orglett.9b00465. Epub 2019 Mar 6.
A novel and efficient CF radical-involved external-catalyst-free trifluoromethylation/cyclization methodology to access a group of new trifluoromethylated dihydroisoquinolinones was developed, by reacting different N-allylbenzamides with Togni-II in one pot under mild reaction conditions. Meanwhile, this external-catalyst-free trifluoromethylation/cyclization protocol was also well suitable for being employed to synthesize many valuable trifluoromethylated N-acetylindolines, by reacting N-aryl- N-allylacetamides with Togni-II. In both reactions, the amide groups of reactants themselves acted as the catalysts to promote the generation of the CF radical required for the following radical-cascade trifluoromethylation/cyclization reactions.
通过在温和反应条件下将不同的N-烯丙基苯甲酰胺与Togni-II一锅反应，开发了一种新颖且高效的、涉及CF自由基的无外部催化剂的三氟甲基化/环化方法，用于合成一系列新型三氟甲基化二氢异喹啉酮。同时，这种无外部催化剂的三氟甲基化/环化方案也非常适合用于合成许多有价值的三氟甲基化N-乙酰基吲哚啉，即将N-芳基-N-烯丙基乙酰胺与Togni-II反应。在这两个反应中，反应物自身的酰胺基团充当催化剂，以促进后续自由基级联三氟甲基化/环化反应所需的CF自由基的生成。
