Rhodium(III)-Catalyzed Regioselective C-H Allylation and Prenylation of Indoles at C4-Position

Herein, Rh(III)-catalyzed C4-selective C-H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. Scale-up experiment and mechanistic studies were also accomplished.

Automated summary

In this study, Rh(III)-catalyzed C-H allylation and prenylation of indoles using a weak carbonyl coordination directing group have been reported, providing various allylated and prenylated indoles in moderate to satisfied yields. These reactions demonstrate high functional-groups compatibility and broad substrate scope, making them potentially valuable in organic synthesis. Scale-up experiments and mechanistic studies were also conducted to further investigate this transformation.