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

doi:10.1021/acs.orglett.0c01270

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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38 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 language	English (US)
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.0c01270
State	Published - 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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10.1021/acs.orglett.0c01270

https://repository.kaust.edu.sa/bitstream/10754/662838/1/Manuscript_accepted.%20Maganese.pdf

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

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.",

author = "Borghs, {Jannik C.} and Viktoriia Zubar and {Azofra Mesa}, Luis and Jan Sklyaruk and Magnus Rueping",

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.",

year = "2020",

month = may,

day = "13",

doi = "10.1021/acs.orglett.0c01270",

language = "English (US)",

journal = "Organic Letters",

issn = "1523-7060",

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T1 - Manganese-Catalyzed Regioselective Dehydrogenative C- versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation

AU - Borghs, Jannik C.

AU - Zubar, Viktoriia

AU - Azofra Mesa, Luis

AU - Sklyaruk, Jan

AU - Rueping, Magnus

N1 - 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.

PY - 2020/5/13

Y1 - 2020/5/13

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/662838

UR - https://pubs.acs.org/doi/10.1021/acs.orglett.0c01270

UR - http://www.scopus.com/inward/record.url?scp=85085652482&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c01270

DO - 10.1021/acs.orglett.0c01270

M3 - Article

C2 - 32401525

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

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

Abstract

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