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 journalArticlepeer-review

53 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 languageEnglish (US)
Pages (from-to)3083-3088
Number of pages6
JournalCHEMSUSCHEM
Volume12
Issue number13
DOIs
StatePublished - 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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