Palladium-Catalyzed Direct and Specific C-7 Acylation of Indolines with 1,2-Diketones

The indole scaffold is a ubiquitous and useful substructure, and extensive investigations have been conducted to construct the indole framework and/or realize indole modification. Nevertheless, the direct selective functionalization on the benzenoid core must overcome the high activity of the C-3 position and still remains highly challenging. Herein, a palladium-catalyzed direct and specific C-7 acylation of indolines in the presence of an easily removed directing group was developed. This strategy usually is considered as a practical strategy for the preparation of acylated indoles because indoline can be easily converted to indole under oxidation conditions. In particular, our strategy greatly improved the alkacylation yield of indolines for which only an unsatisfactory yield could be achieved in the previous studies. Furthermore, the reaction can be scaled up to gram level in the standard reaction conditions with a much lower palladium loading (1 mol %).

Automated summary

A palladium-catalyzed direct and specific C-7 acylation of indolines in the presence of an easily removed directing group has been developed in this study. This strategy greatly improved the yield of alkacylated indolines and can be scaled up to gram level with a lower palladium loading.