Manganese-Catalyzed Multicomponent Synthesis of Pyrroles through Acceptorless Dehydrogenation Hydrogen Autotransfer Catalysis: Experiment and Computation

Jannik C. Borghs; Luis Miguel Azofra; Tobias Biberger; Oliver Linnenberg; Luigi Cavallo; Magnus Rueping; Osama El-Sepelgy

doi:10.1002/cssc.201802416

Manganese-Catalyzed Multicomponent Synthesis of Pyrroles through Acceptorless Dehydrogenation Hydrogen Autotransfer Catalysis: Experiment and Computation

Jannik C. Borghs, Luis Miguel Azofra, Tobias Biberger, Oliver Linnenberg, Luigi Cavallo^*, Magnus Rueping, Osama El-Sepelgy

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

Abstract

A new base metal catalyzed sustainable multicomponent synthesis of pyrroles from readily available substrates is reported. The developed protocol utilizes an air- and moisture-stable catalyst system and enables the replacement of themutagenic α-haloketones with readily abundant 1,2-diols. Moreover, the presented method is catalytic in base and the sole byproducts of this transformation are water and hydrogen gas. Experimental and computational mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation hydrogen autotransfer methodology.

Original language	English (US)
Pages (from-to)	3083-3088
Number of pages	6
Journal	CHEMSUSCHEM
Volume	12
Issue number	13
DOIs	https://doi.org/10.1002/cssc.201802416
State	Published - Jul 5 2019

Bibliographical note

Funding Information:
J.C.B. is thankful for the financial support of the German Federal Environmental Foundation (DBU). L.M.A. and L.C. acknowledge King Abdullah University of Science and Technology (KAUST) for support. We thank KAUST Supercomputing Laboratory for use of the supercomputer Shaheen II and providing the computational resources.

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

acceptorless dehydrogenation
alcohols
base metals
heterocycles
hydrogen autotransfer

ASJC Scopus subject areas

Environmental Chemistry
General Chemical Engineering
General Materials Science
General Energy

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10.1002/cssc.201802416

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title = "Manganese-Catalyzed Multicomponent Synthesis of Pyrroles through Acceptorless Dehydrogenation Hydrogen Autotransfer Catalysis: Experiment and Computation",

abstract = "A new base metal catalyzed sustainable multicomponent synthesis of pyrroles from readily available substrates is reported. The developed protocol utilizes an air- and moisture-stable catalyst system and enables the replacement of themutagenic α-haloketones with readily abundant 1,2-diols. Moreover, the presented method is catalytic in base and the sole byproducts of this transformation are water and hydrogen gas. Experimental and computational mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation hydrogen autotransfer methodology.",

keywords = "acceptorless dehydrogenation, alcohols, base metals, heterocycles, hydrogen autotransfer",

author = "Borghs, {Jannik C.} and Azofra, {Luis Miguel} and Tobias Biberger and Oliver Linnenberg and Luigi Cavallo and Magnus Rueping and Osama El-Sepelgy",

note = "Funding Information: J.C.B. is thankful for the financial support of the German Federal Environmental Foundation (DBU). L.M.A. and L.C. acknowledge King Abdullah University of Science and Technology (KAUST) for support. We thank KAUST Supercomputing Laboratory for use of the supercomputer Shaheen II and providing the computational resources. Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/cssc.201802416",

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AU - Borghs, Jannik C.

AU - Azofra, Luis Miguel

AU - Biberger, Tobias

AU - Linnenberg, Oliver

AU - Cavallo, Luigi

AU - Rueping, Magnus

AU - El-Sepelgy, Osama

N1 - Funding Information: J.C.B. is thankful for the financial support of the German Federal Environmental Foundation (DBU). L.M.A. and L.C. acknowledge King Abdullah University of Science and Technology (KAUST) for support. We thank KAUST Supercomputing Laboratory for use of the supercomputer Shaheen II and providing the computational resources. Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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N2 - A new base metal catalyzed sustainable multicomponent synthesis of pyrroles from readily available substrates is reported. The developed protocol utilizes an air- and moisture-stable catalyst system and enables the replacement of themutagenic α-haloketones with readily abundant 1,2-diols. Moreover, the presented method is catalytic in base and the sole byproducts of this transformation are water and hydrogen gas. Experimental and computational mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation hydrogen autotransfer methodology.

AB - A new base metal catalyzed sustainable multicomponent synthesis of pyrroles from readily available substrates is reported. The developed protocol utilizes an air- and moisture-stable catalyst system and enables the replacement of themutagenic α-haloketones with readily abundant 1,2-diols. Moreover, the presented method is catalytic in base and the sole byproducts of this transformation are water and hydrogen gas. Experimental and computational mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation hydrogen autotransfer methodology.

KW - acceptorless dehydrogenation

KW - alcohols

KW - base metals

KW - heterocycles

KW - hydrogen autotransfer

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ER -

Manganese-Catalyzed Multicomponent Synthesis of Pyrroles through Acceptorless Dehydrogenation Hydrogen Autotransfer Catalysis: Experiment and Computation

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

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