Organic photoredox catalyzed C(sp3)-H functionalization of saturated aza-heterocycles via a cross-dehydrogenative coupling reaction.

Herein we present a novel protocol to access α-functionalized saturated aza-heterocycles, and a variety of nucleophilic groups, such as indole, naphthol, phenol, pyrrole, furyl, nitromethyl, and cyano, could be easily installed into saturated aza-heterocycles. Furthermore, a range of biologically valuable 3,3'-diindolylmethane derivatives could also be readily accessed under mild photocatalytic conditions.

Organic photoredox catalyzed dealkylation/acylation of tertiary amines to access amides.

A mild metal-free C-N bond activation strategy for the direct conversion of inert tertiary amines with acyl chlorides into tertiary amides via organic photoredox catalysis is presented. In this protocol, a novel organic photocatalyst (Cz-NI-Ph) that showed excellent catalytic performance during C-N bond cleavage is developed. Moreover, this reaction features green and mild conditions, broad substrate scope, and readily available raw materials.

Organic photoredox catalytic amino-heteroarylation of unactivated olefins to access distal amino ketones.

Here we describe a metal-free amino-heteroarylation of unactivated olefins via organic photoredox catalysis, providing a concise and efficient approach for the rapid synthesis of various δ (ß, ε)-amino ketones under mild conditions. This protocol demonstrates that the new photocatalyst Cz-NI developed by our group has an excellent photoredox catalytic performance. Finally, a series of mechanistic experiments and DFT calculations indicate that this transformation undergoes a photoredox catalytic sequential radical addition/functional group migration process.