Manna Manash Kumar, Bhunia Samir Kumar, Jana Ranjan
Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical, Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata-700032, West Bengal, India.
Chem Commun (Camb). 2017 Jun 22;53(51):6906-6909. doi: 10.1039/c7cc03053c.
Herein, we report a ruthenium-catalyzed 1,2-carboamination through C-H activation for the synthesis of 2-arylindolines from readily available, inexpensive, protected anilines and vinyl arenes. In earlier reports, indoline synthesis through C-H activation was demonstrated using sterically or electronically biased olefins suppressing β-hydride elimination. However, in the present protocol a ruthenium(ii)-catalyzed indoline synthesis via interrupted Heck-type manifold with unbiased styrenes is demonstrated. Mechanistically, the reaction proceeds through pyrimidine directed electrophilic ortho metalation, alkene insertion, amine coordination, and reductive elimination to construct the indoline nucleus.
在此，我们报道了一种钌催化的通过C-H活化进行的1,2-碳胺化反应，用于从易得、廉价的受保护苯胺和乙烯基芳烃合成2-芳基吲哚啉。在早期报道中，通过使用空间位阻或电子偏向的烯烃抑制β-氢消除，展示了通过C-H活化合成吲哚啉。然而，在本方法中，展示了一种通过具有非偏向苯乙烯的间断Heck型历程的钌（II）催化吲哚啉合成。从机理上讲，该反应通过嘧啶导向的亲电邻位金属化、烯烃插入、胺配位和还原消除来构建吲哚啉核。
