Rh(CAAC)-Catalyzed Arene Hydrogenation: Evidence for Nanocatalysis and Sterically Controlled Site-Selective Hydrogenation
Abstract
We report the hydrogenation of aromatic groups at room temperature and low hydrogen pressure by [(CAAC)Rh(COD)Cl] (CAAC = cyclic alkyl amino carbene), which was generated from the reaction of free CAAC and [Rh(COD)Cl]2. Facile access to the molecular catalyst precursor, mild reaction conditions, and operational simplicity are notable advantages that allow for kinetic, mechanistic, and spectroscopic studies to elucidate the nature of the catalyst. The cumulative results of these studies, which support the formation of a heterogeneous catalyst from a molecular CAAC-Rh precursor for arene hydrogenation, contrast with that of a previously reported homogeneous CAAC-rhodium catalyst for arene hydrogenation. We determined the site selectivity of this arene hydrogenation system through detailed competition experiments in small molecules bearing aromatic rings of varying electronic and steric influence. With the growing popularity of CAAC ligands in synthetic inorganic chemistry and homogeneous catalysis, this work illustrates the remarkable potential of CAAC ligands in the modification and stabilization of heterogeneous catalysts, in light of the burgeoning interest in organometallic approaches using structurally well-defined precursors for the controlled generation of nanocatalysts.
- Publication Date:
- Research Org.:
- Argonne National Lab. (ANL), Argonne, IL (United States); Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1492981
- Alternate Identifier(s):
- OSTI ID: 1822163
- Report Number(s):
- PNNL-SA-130529
Journal ID: ISSN 2155-5435
- Grant/Contract Number:
- AC05-76RL01830
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ACS Catalysis
- Additional Journal Information:
- Journal Volume: 8; Journal Issue: 9; Journal ID: ISSN 2155-5435
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- ENGLISH
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; hydrogenation; site selectivity; arene; nanoparticle
Citation Formats
Tran, Ba L., Fulton, John L., Linehan, John C., Lercher, Johannes A., and Bullock, Ronald Morris. Rh(CAAC)-Catalyzed Arene Hydrogenation: Evidence for Nanocatalysis and Sterically Controlled Site-Selective Hydrogenation. United States: N. p., 2018.
Web. doi:10.1021/acscatal.8b02589.
Tran, Ba L., Fulton, John L., Linehan, John C., Lercher, Johannes A., & Bullock, Ronald Morris. Rh(CAAC)-Catalyzed Arene Hydrogenation: Evidence for Nanocatalysis and Sterically Controlled Site-Selective Hydrogenation. United States. https://doi.org/10.1021/acscatal.8b02589
Tran, Ba L., Fulton, John L., Linehan, John C., Lercher, Johannes A., and Bullock, Ronald Morris. Mon .
"Rh(CAAC)-Catalyzed Arene Hydrogenation: Evidence for Nanocatalysis and Sterically Controlled Site-Selective Hydrogenation". United States. https://doi.org/10.1021/acscatal.8b02589. https://www.osti.gov/servlets/purl/1492981.
@article{osti_1492981,
title = {Rh(CAAC)-Catalyzed Arene Hydrogenation: Evidence for Nanocatalysis and Sterically Controlled Site-Selective Hydrogenation},
author = {Tran, Ba L. and Fulton, John L. and Linehan, John C. and Lercher, Johannes A. and Bullock, Ronald Morris},
abstractNote = {We report the hydrogenation of aromatic groups at room temperature and low hydrogen pressure by [(CAAC)Rh(COD)Cl] (CAAC = cyclic alkyl amino carbene), which was generated from the reaction of free CAAC and [Rh(COD)Cl]2. Facile access to the molecular catalyst precursor, mild reaction conditions, and operational simplicity are notable advantages that allow for kinetic, mechanistic, and spectroscopic studies to elucidate the nature of the catalyst. The cumulative results of these studies, which support the formation of a heterogeneous catalyst from a molecular CAAC-Rh precursor for arene hydrogenation, contrast with that of a previously reported homogeneous CAAC-rhodium catalyst for arene hydrogenation. We determined the site selectivity of this arene hydrogenation system through detailed competition experiments in small molecules bearing aromatic rings of varying electronic and steric influence. With the growing popularity of CAAC ligands in synthetic inorganic chemistry and homogeneous catalysis, this work illustrates the remarkable potential of CAAC ligands in the modification and stabilization of heterogeneous catalysts, in light of the burgeoning interest in organometallic approaches using structurally well-defined precursors for the controlled generation of nanocatalysts.},
doi = {10.1021/acscatal.8b02589},
journal = {ACS Catalysis},
number = 9,
volume = 8,
place = {United States},
year = {Mon Jul 30 00:00:00 EDT 2018},
month = {Mon Jul 30 00:00:00 EDT 2018}
}
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Scheme 1: Catalytic arene hydrogenations by Rh(CAAC) systems.
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Works referencing / citing this record:
Accessing Difluoromethylated and Trifluoromethylated cis ‐Cycloalkanes and Saturated Heterocycles: Preferential Hydrogen Addition to the Substitution Sites for Dearomatization
journal, November 2019
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- Angewandte Chemie, Vol. 131, Issue 47
Selective Arene Hydrogenation for Direct Access to Saturated Carbo- and Heterocycles
journal, April 2019
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- Angewandte Chemie International Edition, Vol. 58, Issue 31
Hydrierung borylierter Aromaten
journal, December 2018
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- Angewandte Chemie, Vol. 131, Issue 20
Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene–Rhodium Complex: Direct Access to cis ‐Substituted Borylated Cycloalkanes and Saturated Heterocycles
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- Ling, Liang; He, Yuan; Zhang, Xue
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Die selektive Arenhydrierung bietet einen direkten Zugang zu gesättigten Carbo‐ und Heterocyclen
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Ionic Liquid Stabilized Niobium Oxoclusters Catalyzing Oxidation of Sulfides with Exceptional Activity
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- Chemistry – A European Journal, Vol. 25, Issue 16
Recent Advances in the Chemistry of N ‐Heterocyclic‐Carbene‐Functionalized Metal‐Nanoparticles and Their Applications
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Accessing Difluoromethylated and Trifluoromethylated cis -Cycloalkanes and Saturated Heterocycles: Preferential Hydrogen Addition to the Substitution Sites for Dearomatization
journal, October 2019
- Zhang, Xue; Ling, Liang; Luo, Meiming
- Angewandte Chemie International Edition, Vol. 58, Issue 47
Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene–Rhodium Complex: Direct Access to cis ‐Substituted Borylated Cycloalkanes and Saturated Heterocycles
journal, April 2019
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Hydrogenation of Borylated Arenes
journal, May 2019
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