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

dc.contributor.authorBorghs, Jannik C.
dc.contributor.authorZubar, Viktoriia
dc.contributor.authorAzofra Mesa, Luis
dc.contributor.authorSklyaruk, Jan
dc.contributor.authorRueping, Magnus
dc.date.accessioned2020-05-17T08:51:27Z
dc.date.available2020-05-17T08:51:27Z
dc.date.issued2020-05-13
dc.date.submitted2020-04-10
dc.identifier.citationBorghs, 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
dc.identifier.issn1523-7060
dc.identifier.issn1523-7052
dc.identifier.pmid32401525
dc.identifier.doi10.1021/acs.orglett.0c01270
dc.identifier.urihttp://hdl.handle.net/10754/662838
dc.description.abstractThe 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.
dc.description.sponsorshipThis 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.
dc.publisherAmerican Chemical Society (ACS)
dc.relation.urlhttps://pubs.acs.org/doi/10.1021/acs.orglett.0c01270
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.orglett.0c01270.
dc.titleManganese-Catalyzed Regioselective Dehydrogenative C- versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalOrganic Letters
dc.rights.embargodate2021-05-13
dc.eprint.versionPost-print
dc.contributor.institutionInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
dc.contributor.institutionCIDIA-FEAM (Unidad Asociada al Consejo Superior de Investigaciones Científicas, CSIC, avalada por el Instituto de Ciencia de Materiales de Sevilla, Universidad de Sevilla), Instituto de Estudios Ambientales y Recursos Naturales (i-UNAT), Universidad de Las Palmas de Gran Canaria (ULPGC), Campus de Tafira, 35017 Las Palmas de Gran Canaria, Spain
kaust.personZubar, Viktoriia
kaust.personRueping, Magnus
kaust.acknowledged.supportUnitKAUST Supercomputing Laboratory
kaust.acknowledged.supportUnitOffice of Sponsored Research
kaust.acknowledged.supportUnitsupercomputer Shaheen II
dc.date.published-online2020-05-13
dc.date.published-print2020-06-05


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