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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 C 3 - 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.

Manganese-Catalyzed Regioselective Dehydrogenative C- versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation