Iron–iodine co-catalysis towards tandem C–N/C–C bond formation: one-pot regioselective synthesis of 2-amino-3-alkylindoles

Abstract

Herein, we report a novel iron and iodine cooperative catalytic system for intermolecular C2,3−H aminoalkylation of indoles with azoles and xanthenes as the coupling agents, which allows tandem C−N/C−C bond...

Strategies and Mechanisms of First-Row Transition Metal-Regulated Radical C–H Functionalization

“…303 Thereafter, Liang and co-workers reported the Fe/iodine cocatalyzed C(sp 3 )−H heteroarylation of xanthenes with indoles and azoles as coupling partners in 2022 (Scheme 32e). 304 These reactions allowed tandem C−N/ C−C bond formation for the regioselective synthesis of 2amino-3-alkylindoles .…”

Visible light irradiated photocatalytic C(sp3)–H phosphorylation of xanthenes and 9,10-dihydroacridines with P(O)–H compounds

“…Accordingly, the C(sp 3 )–H functionalization at the 9-position of these molecules remains a continuous area of interest for synthetic chemists. Recently, the direct construction of C(sp 3 )–C, C(sp 3 )–N, and C(sp 3 )–S bonds for the synthesis of 9-substituted xanthene derivatives has been realized by Cozzi, 3 Klussmann, 4 Jiao, 5 Yorimitsu, 6 Pericàs, 7 Zeng, 8 Loh, 9 Chen, 10 Li, 11 Gong, 12 Li, 13 Deb, 14 Wang, 15 and Liang 16 by using different strategies including transition metal catalysis, oxidative dehydrogenative cross-coupling, photoredox catalysis, and electrolysis. On the other hand, organophosphorus compounds bearing C(sp 3 )–P bonds have been of particular interest due to their broad applications in organic synthesis, medicinal chemistry, agrochemicals, flame retardants, and extractants.…”

“…The use of MsOH or TfOH instead of TsOH resulted in a lower yield (entries 14 and 15). Control experiments showed that visible light, PC, and the oxygen atmosphere are critical to the success of the reaction (entries [16][17][18]. Although the reaction could proceed under an air atmosphere, 3aa was obtained in a poor yield (entry 19).…”