Pd-Catalyzed Dearomatization of Indole Derivatives via Intermolecular Heck Reactions

The Summary of main observation and conclusion Pd-catalyzed intermolecular dearomative Heck reaction of indoles with aryl iodides is described. The challenges on both reactivity and regioselectivity are addressed by the judicious regulation of the geometric and electronic properties of the substrates. An array of indoline derivatives bearing C2-quaternary center is obtained in good to excellent yields (up to 93%) with exclusive regioselectivity under operationally simple conditions. The mechanistic proposal is supported by detailed DFT calculations.