Rhodium-Catalyzed Regioselective C7-Functionalization of N-Pivaloylindoles

The indole ring system is one of the most ubiquitous heterocycles in nature and plays an irreplaceable role in medicinal, material and agricultural chemistry. In the last decade, substantial progress has been made in the field of transition metal-catalyzed C-H bond functionalization, which has provided a green, general and straightforward approach for assembling substituted indoles. On account of the higher electron density at the 2- and 3-positions, a number of approaches have been reported for the introduction of a functional group at the 2-, 3-, 4- position of indole regioselectively. However, selective direct functionalization at the 7-position remains challenging, owing to the inherently poor reactivity of this carbon center. In our recent work, we have developed an efficient rhodium-catalyzed method for direct C-H functionalization at the C7 position using N-pivaloyl as a suitable directing group. Good to excellent yields of alkenylation products were observed with acrylates, styrenes, and vinyl phenyl sulfones, whereas the saturated alkylation products were obtained in good yield with α,β-unsaturated ketones. Further studies on mechanism and other related regioselective  C7 functionalization of indole reactions are currently under investigation (Angew. Chem. Int. Ed. 2016, 55, 321-325.).

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