Catalytic Transfer Hydrogenation of Arenes and Heteroarenes

Coralie Gelis; Arne Heusler; Zackaria Nairoukh; Frank Glorius

doi:10.1002/chem.202002777

Catalytic Transfer Hydrogenation of Arenes and Heteroarenes

Coralie Gelis, Arne Heusler, Zackaria Nairoukh, Frank Glorius^*

^*Corresponding author for this work

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

16 Scopus citations

Abstract

Transfer hydrogenation reactions are of great interest to reduce diverse molecules under mild reaction conditions. To date, this type of reaction has only been successfully applied to alkenes, alkynes and polarized unsaturated compounds such as ketones, imines, pyridines, etc. The reduction of benzene derivatives by transfer hydrogenation has never been described, which is likely due to the high energy barrier required to dearomatize these compounds. In this context, we have developed a catalytic transfer hydrogenation reaction for the reduction of benzene derivatives and heteroarenes to form complex 3-dimensional scaffolds bearing various functional groups at room temperature without needing compressed hydrogen gas.

Original language	American English
Pages (from-to)	14090-14094
Number of pages	5
Journal	Chemistry - A European Journal
Volume	26
Issue number	62
DOIs	https://doi.org/10.1002/chem.202002777
State	Published - 6 Nov 2020
Externally published	Yes

Bibliographical note

Funding Information:
We thank the European Research Council (ERC Advanced Grant Agreement no. 788558), the Alexander von Humboldt Foundation (C.G.), the Alfried Krupp von Bohlen and Hallbach Foundation (A.H.) and the Hans‐Jensen‐Minerva Foundation (Z.N.) for generous financial support. The authors also thank Dr. Michael J. James for helpful discussions, Matthias Freitag, Martin Bühner (nanoAnalyticsGmbH) for SEM analysis and Dr. Klaus Bergander for NMR measurements. Open access funding enabled and organized by Projekt DEAL.

Funding Information:
We thank the European Research Council (ERC Advanced Grant Agreement no. 788558), the Alexander von Humboldt Foundation (C.G.), the Alfried Krupp von Bohlen and Hallbach Foundation (A.H.) and the Hans-Jensen-Minerva Foundation (Z.N.) for generous financial support. The authors also thank Dr. Michael J. James for helpful discussions, Matthias Freitag, Martin Bühner (nanoAnalyticsGmbH) for SEM analysis and Dr. Klaus Bergander for NMR measurements. Open access funding enabled and organized by Projekt DEAL.

Publisher Copyright:
© 2020 The Authors. Published by Wiley-VCH GmbH

Keywords

arene reduction
catalysis
organic chemistry
rhodium
transfer hydrogenation

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10.1002/chem.202002777

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title = "Catalytic Transfer Hydrogenation of Arenes and Heteroarenes",

abstract = "Transfer hydrogenation reactions are of great interest to reduce diverse molecules under mild reaction conditions. To date, this type of reaction has only been successfully applied to alkenes, alkynes and polarized unsaturated compounds such as ketones, imines, pyridines, etc. The reduction of benzene derivatives by transfer hydrogenation has never been described, which is likely due to the high energy barrier required to dearomatize these compounds. In this context, we have developed a catalytic transfer hydrogenation reaction for the reduction of benzene derivatives and heteroarenes to form complex 3-dimensional scaffolds bearing various functional groups at room temperature without needing compressed hydrogen gas.",

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author = "Coralie Gelis and Arne Heusler and Zackaria Nairoukh and Frank Glorius",

note = "Funding Information: We thank the European Research Council (ERC Advanced Grant Agreement no. 788558), the Alexander von Humboldt Foundation (C.G.), the Alfried Krupp von Bohlen and Hallbach Foundation (A.H.) and the Hans‐Jensen‐Minerva Foundation (Z.N.) for generous financial support. The authors also thank Dr. Michael J. James for helpful discussions, Matthias Freitag, Martin B{\"u}hner (nanoAnalyticsGmbH) for SEM analysis and Dr. Klaus Bergander for NMR measurements. Open access funding enabled and organized by Projekt DEAL. Funding Information: We thank the European Research Council (ERC Advanced Grant Agreement no. 788558), the Alexander von Humboldt Foundation (C.G.), the Alfried Krupp von Bohlen and Hallbach Foundation (A.H.) and the Hans-Jensen-Minerva Foundation (Z.N.) for generous financial support. The authors also thank Dr. Michael J. James for helpful discussions, Matthias Freitag, Martin B{\"u}hner (nanoAnalyticsGmbH) for SEM analysis and Dr. Klaus Bergander for NMR measurements. Open access funding enabled and organized by Projekt DEAL. Publisher Copyright: {\textcopyright} 2020 The Authors. Published by Wiley-VCH GmbH",

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N2 - Transfer hydrogenation reactions are of great interest to reduce diverse molecules under mild reaction conditions. To date, this type of reaction has only been successfully applied to alkenes, alkynes and polarized unsaturated compounds such as ketones, imines, pyridines, etc. The reduction of benzene derivatives by transfer hydrogenation has never been described, which is likely due to the high energy barrier required to dearomatize these compounds. In this context, we have developed a catalytic transfer hydrogenation reaction for the reduction of benzene derivatives and heteroarenes to form complex 3-dimensional scaffolds bearing various functional groups at room temperature without needing compressed hydrogen gas.

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Catalytic Transfer Hydrogenation of Arenes and Heteroarenes

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