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Despite a growing body of studies on directing-group (DG)-assisted C-H activation strategies, efficient exploitation of the used DG remains underexplored. We developed a rhodium-catalyzed C-H functionalization of indoles at the C4 position using alpha,beta-unsaturated enones as versatile DGs. Combined experimental and theoretical analyses revealed that the C-H activation process was reversible and the course of Rh-carbene generation controlled the overall site-selectivity of the C-H functionalization. The introduced malonate unit and the used enone DG were cyclized in a further C-C bond forming process to assemble 3,4-fused tricyclic indoles in an asymmetric manner. Telescoping the two reaction sequences provided rapid entry into this densely functionalized indole architecture from readily available chemical feedstock.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
,Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles