Frustrated Lewis pair-catalyzed hydrogenation of unactivated alkenes with sterically hindered 9-phosphatriptycenes

Damien Mahaut; Benoît Champagne; Guillaume Berionni

doi:10.1002/cctc.202200294

Frustrated Lewis pair-catalyzed hydrogenation of unactivated alkenes with sterically hindered 9-phosphatriptycenes

Damien Mahaut, Benoît Champagne, Guillaume Berionni

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

Abstract

The frustrated Lewis pair-catalyzed hydrogenation of unactivated alkenes with H₂ is reported. The weak Lewis basicity and high steric hindrance of ortho-substituted 9-phosphatriptycene derivatives is taken as an advantage to catalyze this reaction in combination with tris(pentafluorophenyl)borane. A scope of unsaturated substrates is described. The thermodynamics and kinetics of hydrogenation investigated by density functional theory show that the protonation of the olefin by the strongly acidic phosphonium cation is the critical step of the reaction.

Original language	English
Article number	e202200294
Journal	ChemCatChem
Volume	14
Issue number	13
DOIs	https://doi.org/10.1002/cctc.202200294
Publication status	Published - 7 Jul 2022

Keywords

9-phosphatriptycenes
density functional theory
frustrated Lewis pairs
hydrogenation
unactivated alkenes

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10.1002/cctc.202200294

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@article{18eb6eeb210f47e8a9ca7ef4d15ab862,

title = "Frustrated Lewis pair-catalyzed hydrogenation of unactivated alkenes with sterically hindered 9-phosphatriptycenes",

abstract = "The frustrated Lewis pair-catalyzed hydrogenation of unactivated alkenes with H2 is reported. The weak Lewis basicity and high steric hindrance of ortho-substituted 9-phosphatriptycene derivatives is taken as an advantage to catalyze this reaction in combination with tris(pentafluorophenyl)borane. A scope of unsaturated substrates is described. The thermodynamics and kinetics of hydrogenation investigated by density functional theory show that the protonation of the olefin by the strongly acidic phosphonium cation is the critical step of the reaction.",

keywords = "9-phosphatriptycenes, density functional theory, frustrated Lewis pairs, hydrogenation, unactivated alkenes",

author = "Damien Mahaut and Beno{\^i}t Champagne and Guillaume Berionni",

note = "Funding Information: We acknowledge the University of Namur and the Fonds de la Recherche Scientifique‐FNRS (F.R.S.‐FNRS) (FRIA PhD grant 1.E.086.20 for DM and PDR project T.0012.21 for GB) for financial support. The calculations were performed on the computers of the Consortium des {\'E}quipements de Calcul Intensif and particularly those of the High‐Performance Computing Platform, which are supported by the FNRS‐FRFC, the Walloon Region, and the University of Namur (Conventions No. GEQ U.G006.15, U.G018.19, 1610468, and RW/GEQ2016). The PC2 platform is acknowledged for technical support in the recording of NMR spectra. Finally, we thank Dr. Aur{\'e}lien Chardon for helpful discussions and guidance, and Dr. Lei Hu for practical help during the hydrogenation reactions and for helpful discussions on the reactivity of phosphatriptycenes. Funding Information: We acknowledge the University of Namur and the Fonds de la Recherche Scientifique-FNRS (F.R.S.-FNRS) (FRIA PhD grant 1.E.086.20 for DM and PDR project T.0012.21 for GB) for financial support. The calculations were performed on the computers of the Consortium des {\'E}quipements de Calcul Intensif and particularly those of the High-Performance Computing Platform, which are supported by the FNRS-FRFC, the Walloon Region, and the University of Namur (Conventions No. GEQ U.G006.15, U.G018.19, 1610468, and RW/GEQ2016). The PC2 platform is acknowledged for technical support in the recording of NMR spectra. Finally, we thank Dr. Aur{\'e}lien Chardon for helpful discussions and guidance, and Dr. Lei Hu for practical help during the hydrogenation reactions and for helpful discussions on the reactivity of phosphatriptycenes. Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = jul,

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doi = "10.1002/cctc.202200294",

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T1 - Frustrated Lewis pair-catalyzed hydrogenation of unactivated alkenes with sterically hindered 9-phosphatriptycenes

AU - Mahaut, Damien

AU - Champagne, Benoît

AU - Berionni, Guillaume

N1 - Funding Information: We acknowledge the University of Namur and the Fonds de la Recherche Scientifique‐FNRS (F.R.S.‐FNRS) (FRIA PhD grant 1.E.086.20 for DM and PDR project T.0012.21 for GB) for financial support. The calculations were performed on the computers of the Consortium des Équipements de Calcul Intensif and particularly those of the High‐Performance Computing Platform, which are supported by the FNRS‐FRFC, the Walloon Region, and the University of Namur (Conventions No. GEQ U.G006.15, U.G018.19, 1610468, and RW/GEQ2016). The PC2 platform is acknowledged for technical support in the recording of NMR spectra. Finally, we thank Dr. Aurélien Chardon for helpful discussions and guidance, and Dr. Lei Hu for practical help during the hydrogenation reactions and for helpful discussions on the reactivity of phosphatriptycenes. Funding Information: We acknowledge the University of Namur and the Fonds de la Recherche Scientifique-FNRS (F.R.S.-FNRS) (FRIA PhD grant 1.E.086.20 for DM and PDR project T.0012.21 for GB) for financial support. The calculations were performed on the computers of the Consortium des Équipements de Calcul Intensif and particularly those of the High-Performance Computing Platform, which are supported by the FNRS-FRFC, the Walloon Region, and the University of Namur (Conventions No. GEQ U.G006.15, U.G018.19, 1610468, and RW/GEQ2016). The PC2 platform is acknowledged for technical support in the recording of NMR spectra. Finally, we thank Dr. Aurélien Chardon for helpful discussions and guidance, and Dr. Lei Hu for practical help during the hydrogenation reactions and for helpful discussions on the reactivity of phosphatriptycenes. Publisher Copyright: © 2022 Wiley-VCH GmbH.

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N2 - The frustrated Lewis pair-catalyzed hydrogenation of unactivated alkenes with H2 is reported. The weak Lewis basicity and high steric hindrance of ortho-substituted 9-phosphatriptycene derivatives is taken as an advantage to catalyze this reaction in combination with tris(pentafluorophenyl)borane. A scope of unsaturated substrates is described. The thermodynamics and kinetics of hydrogenation investigated by density functional theory show that the protonation of the olefin by the strongly acidic phosphonium cation is the critical step of the reaction.

AB - The frustrated Lewis pair-catalyzed hydrogenation of unactivated alkenes with H2 is reported. The weak Lewis basicity and high steric hindrance of ortho-substituted 9-phosphatriptycene derivatives is taken as an advantage to catalyze this reaction in combination with tris(pentafluorophenyl)borane. A scope of unsaturated substrates is described. The thermodynamics and kinetics of hydrogenation investigated by density functional theory show that the protonation of the olefin by the strongly acidic phosphonium cation is the critical step of the reaction.

KW - 9-phosphatriptycenes

KW - density functional theory

KW - frustrated Lewis pairs

KW - hydrogenation

KW - unactivated alkenes

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DO - 10.1002/cctc.202200294

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SN - 1867-3880

VL - 14

JO - ChemCatChem

JF - ChemCatChem

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ER -

Frustrated Lewis pair-catalyzed hydrogenation of unactivated alkenes with sterically hindered 9-phosphatriptycenes

Abstract

Keywords

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High Performance Computing Technology Platform

Physical Chemistry and characterization(PC2)

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Frustrated Lewis pair-catalyzed hydrogenation of unactivated alkenes with sterically hindered 9-phosphatriptycenes

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Equipment

High Performance Computing Technology Platform

Physical Chemistry and characterization(PC2)

Cite this