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The direct CH-alkylation of indoles using carboxylic acids is presented for the first time. The catalytic system based on the combination of Co(acac) 3 and 1,1,1-tris(diphenylphosphinomethyl)-ethane (Triphos, L1 ), in the presence of Al(OTf) 3 as co-catalyst, is able to perform the reductive alkylation of 2-methyl-1 H -indole with a wide range of carboxylic acids. The utility of the protocol was further demonstrated through the C3 alkylation of several substituted indole derivatives using acetic, phenylacetic or diphenylacetic acids. In addition, a careful selection of the reaction conditions allowed to perform the selective C3 alkenylation of some indole derivatives. Moreover, the alkenylation of C2 position of 3-methyl-1 H -indole was also possible. Control experiments indicate that the aldehyde, in situ formed from the carboxylic acid hydrogenation, plays a central role in the overall process. This new protocol enables the direct functionalization of indoles with readily available and stable carboxylic acids using a non-precious metal based catalyst and hydrogen as reductant.

Cobalt-catalysed reductive C–H alkylation of indoles using carboxylic acids and molecular hydrogen