Manganese-Catalyzed Regioselective Dehydrogenative C- versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation
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ArticleKAUST Department
Chemical Science ProgramKAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2020-05-13Online Publication Date
2020-05-13Print Publication Date
2020-06-05Embargo End Date
2021-05-13Submitted Date
2020-04-10Permanent link to this record
http://hdl.handle.net/10754/662838
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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 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.0c01270Sponsors
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 LettersPubMed ID
32401525Additional Links
https://pubs.acs.org/doi/10.1021/acs.orglett.0c01270ae974a485f413a2113503eed53cd6c53
10.1021/acs.orglett.0c01270
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