Amides and thioamides have been found to serve as nucleophiles for a mild an efficient alkene hydro-functionalization reaction that gives selectivity for the anti-Markovnikov regioisomeric products. This method employs a 9-mesityl-10-methylacridinium tetrafluoroborate complex as a photoredox catalyst, alongside catalytic quantities of thiophenols, which act as hydrogen atom donors. This method can be used for the rapid construction of nitrogen-containing, unsaturated heterocycles. Tuning the electronic properties of the thiophenol co-catalyst has been found to be necessary to obtain high yields with challenging substrates.

Anti-Markovnikov alkene hydrofunctionalizations using amide an thioamide nucleophiles

248th National Meeting (2014)

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