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[17] In this context, the development of efficient and mild methods for indole borylation has attracted increasing attention for research on the preparation of complex indoles. Although the use of a 1-adamantanoyl group can provide the desired indole C-H borylation products with high reactivity and selectivity, removing the directing group requires additional steps (Figure 4). Keywords: C-H bond activation; borylation; indoles; BBr 3; site selectivity; metal-free reaction EN C-H bond activation borylation indoles BBr 3 site selectivity metal-free reaction 2220 2226 7 10/31/23 20231127 NES 231127 Graph The indole ring system is one the most common heterocycles, present in many natural products and pharmaceuticals. [22] C2-Borylated indoles are versatile synthetic intermediates used to build 2,3-disubstituted indole skeletons as key intermediates in total syntheses of natural products and pharmaceuticals (Figure 1 A). [Extracted from the article]