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Rh(III)-Catalyzed [3 + 2] Annulation of Aniline Derivatives with Vinylsilanes via C–H Activation/Alkene Cyclization: Access to Highly Regioselective Indoline Derivatives
ACS Catalysis ( IF 12.9 ) Pub Date : 2021-09-22 , DOI: 10.1021/acscatal.1c03603
Shrikant M. Khake 1 , Naoto Chatani 1
Affiliation  

The Rh(III)-catalyzed reaction of aniline derivatives that contain a pyrimidine directing group with vinylsilanes results in the formation of C3-substituted indoline derivatives in a highly regioselective manner via a C–H activation/alkene cyclization cascade. The results of the mechanistic experiments indicate that C–H bond cleavage is not the rate-determining step and that the reaction proceeds via the formation of a six-membered rhodacycle as a key catalytic species through a pyrimidine-directed electrophilic ortho-C–H rhodation.

中文翻译:

Rh(III)-催化的 [3 + 2] 苯胺衍生物与乙烯基硅烷通过 C–H 活化/烯烃环化的环化:获得高度区域选择性的二氢吲哚衍生物

含有嘧啶导向基团的苯胺衍生物在 Rh(III) 催化下与乙烯基硅烷反应,通过C-H 活化/烯烃环化级联反应以高度区域选择性的方式形成 C3 取代的二氢吲哚衍生物。机理实验的结果表明,C-H 键断裂不是速率决定步骤,反应通过形成六元红环作为关键催化物种通过嘧啶定向的亲电-C-H 进行。罗丹宁。
更新日期:2021-10-01
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