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Radical Trifluoromethylative Dearomatization of Indoles and Furans with CO2
ACS Catalysis ( IF 12.9 ) Pub Date : 2017-11-07 00:00:00 , DOI: 10.1021/acscatal.7b02533
Jian-Heng Ye 1 , Lei Zhu 2 , Si-Shun Yan 1 , Meng Miao 1 , Xin-Chi Zhang 1 , Wen-Jun Zhou 1 , Jing Li 1 , Yu Lan 2 , Da-Gang Yu 1
Affiliation  

Disclosed herein is a versatile and practical strategy for catalytic radical dearomatization. By means of this strategy, we realized the trifluoromethylative dearomatization of indoles and furans with CO2 via Cu catalysis. We also demonstrated the dearomatization of indoles with C-3 C–O bond formation to generate spirocyclic indolines. A variety of important CF3-containing spirocyclic indolines and spiroacetals can be synthesized with atmospheric CO2 under mild reaction conditions. Moreover, these multicomponent reactions feature high selectivity, good functional group tolerance, broad substrate scope, and easy scalability. Further theoretical investigation indicates that this transformation starts with deprotonation of the amine and CO2 insertion, after which CF3· radical addition to the indole followed by intramolecular C–O coupling affords the oxazolidone product.

中文翻译:

CO 2对吲哚和呋喃的自由基三氟甲基化脱芳香化作用

本文公开了用于催化自由基脱芳香化的通用且实用的策略。通过这种策略,我们通过Cu催化实现了CO 2对吲哚和呋喃的三氟甲基化脱芳香化作用。我们还证明了具有C-3 C–O键形成的吲哚脱芳香化生成螺环二氢吲哚。在温和的反应条件下,可以用大气CO 2合成各种重要的含CF 3的螺二氢吲哚和螺缩醛。此外,这些多组分反应具有高选择性,良好的官能团耐受性,广泛的底物范围和易于扩展的特点。进一步的理论研究表明,这种转变始于胺和CO 2的去质子化插入,然后将CF 3 ·自由基加到吲哚中,然后进行分子内C-O偶联,得到恶唑烷酮产物。
更新日期:2017-11-07
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