Para-Selective Dehydrogenative Phenothiazination of Hydroquinolines and Indolines.

Nitrogen-containing heterocyclic systems, such as hydroquinolines, indolines, and phenothiazines, are prevalent in pharmaceuticals, natural products, and organic materials. It is therefore important to develop novel reaction strategies that give access to such biologically relevant scaffolds. This report demonstrates a novel robust, para-selective C-N bond formation between phenothiazines and quinolines or indolines under extremely mild and user-friendly conditions. Furthermore, we bring forward a surprising discovery arising from the homocoupling of indolines through an unprecedented C5-H functionalization.