Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064, P.R. China.
College of Chemistry and Chemical Engineering, Neijiang Normal University, Neijiang, 641112, P.R. China.
Angew Chem Int Ed Engl. 2016 Aug 16;55(34):10022-6. doi: 10.1002/anie.201603352. Epub 2016 Jul 14.
Reported is the first oxy-trifluoromethylation of allylamines with carbon dioxide (CO2 ) using copper catalysis, thus leading to important CF3 -containing 2-oxazolidones. It is also the first time CO2 , a nontoxic and easily available greenhouse gas, has been used to tune the difunctionalization of alkenes from amino- to oxy-trifluoromethylation. Of particular note, this multicomponent reaction is highly chemo-, regio-, and diastereoselective under redox-neutral and mild reaction conditions. Moreover, these reactions feature good functional-group tolerance, broad substrate scope, easy scalability and facile product diversification. The important products could also be formed with either spirocycles or two adjacent tetrasubstituted carbon centers.
报道了首例铜催化下二氧化碳（CO2）与烯丙胺的氧三氟甲基化反应，从而得到了重要的含 CF3 的 2-噁唑烷酮。这也是首次使用无毒且易于获得的温室气体 CO2 来调节烯烃的双官能团化反应，从氨基到氧三氟甲基化。值得特别注意的是，该多组分反应在氧化还原中性和温和的反应条件下具有高度的化学选择性、区域选择性和非对映选择性。此外，这些反应还具有良好的官能团耐受性、广泛的底物范围、易于规模化和易于进行产物多样化。重要的产物也可以形成螺环或两个相邻的四取代碳中心。
