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

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 and Magnus Rueping
Organic letters, Vol.22(11), pp.4222-4227
05/06/2020
PMID: 32401525

Abstract

Chemistry Chemistry, Organic Physical Sciences Science & Technology
The first base metal-catalyzed regioselective dehydrogenative alkylation of indolines using readily available alcohols as the alkylating reagent is reported. A single air- and moisturestable 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.

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