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

Jannik C. Borghs, Viktoriia Zubar, Luis Azofra Mesa, Jan Sklyaruk, Magnus Rueping

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30 Scopus citations

Abstract

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.
Original languageEnglish (US)
JournalOrganic Letters
DOIs
StatePublished - May 13 2020

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (FCC/1/1974). We thank KAUST Supercomputing Laboratory for use of the supercomputer Shaheen II and providing the computational resources.

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