Manganese-Catalyzed Regioselective Dehydrogenative C- versus N‑Alkylation Enabled by a Solvent Switch: Experiment and Computation
Jannik C. Borghs, Viktoriia Zubar, Luis Miguel Azofra, Jan Sklyaruk, Magnus Rueping
Organic Letters, (2020)
Catalysts, Indoles, Aromatic compounds, Alcohols, Organic reactions
The first base metal-catalyzed regioselective dehydrogenative alkylation of indolines using readily available alcohols as the alkylating reagent is reported. A single air- and moisture-stable manganese catalyst provides access to either C3- or N-alkylated indoles depending on the solvent used. Mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation and hydrogen autotransfer strategy.