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

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Type
Article
Authors
Borghs, Jannik C.
Zubar, Viktoriia
Azofra Mesa, Luis cc
Sklyaruk, Jan
Rueping, Magnus cc
KAUST Department
Chemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2020-05-13
Online Publication Date
2020-05-13
Print Publication Date
2020-06-05
Embargo End Date
2021-05-13
Submitted Date
2020-04-10
Permanent link to this record
http://hdl.handle.net/10754/662838

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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.
Citation
Borghs, J. C., Zubar, V., Azofra, L. M., Sklyaruk, J., & Rueping, M. (2020). Manganese-Catalyzed Regioselective Dehydrogenative C- versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation. Organic Letters. doi:10.1021/acs.orglett.0c01270
Sponsors
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.
Publisher
American Chemical Society (ACS)
Journal
Organic Letters
DOI
10.1021/acs.orglett.0c01270
PubMed ID
32401525
Additional Links
https://pubs.acs.org/doi/10.1021/acs.orglett.0c01270
Collections
Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)