Selective C–H acylation of indoles with α-oxocarboxylic acids at the C4 position by palladium catalysis?

Chemical Communications Pub Date: 2019-06-18 DOI: 10.1039/C9CC03893K

Abstract

The first Pd-catalyzed direct C–H acylation of indoles at the C4 position with α-oxocarboxylic acids using a ketone directing group is described. This reaction exhibits high regioselectivity with the tolerance of a wide scope of functional groups to afford diverse acylated indoles in moderate-to-good yields. The control experiments evidence the generation of acyl radicals via K2S2O8 promoted decarboxylation of α-oxocarboxylic acids and the involvement of a PdII/PdIV catalytic cycle. Importantly, the synthetically useful selectivity observed might be applied to prepare indole derivatives with anti-tumor activity as tubulin inhibitors.

Graphical abstract: Selective C–H acylation of indoles with α-oxocarboxylic acids at the C4 position by palladium catalysis
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