Understanding the Reactivity and Decomposition of a Highly Active Iron Pincer Catalyst for Hydrogenation and Dehydrogenation Reactions
Abstract
The iron pincer complex (iPrPNP)Fe(H)(CO) (1, iPrPNP– = N(CH2CH2PiPr2)2-) is an active (pre)catalyst for many hydrogenation and dehydrogenation reactions. This is in part because 1 can reversibly add H2 across the iron-amide bond to form (iPrPNHP)Fe(H)2(CO) (2, iPrPNHP = HN(CH2CH2PiPr2)2). However, rapid decomposition limits the catalytic performance of 1 and related complexes. We explored the pathways through which catalytic intermediates related to 1 and 2 undergo decomposition. This involved characterizing the unstable and previously unobserved complexes [(iPrPNHP)Fe(H)(CO)(L)]+ (5-L; L = THF or N2) and [(iPrPNHP)Fe(H)(H2)(CO)]+ (8), which are proposed as intermediates when 1 and 2 are used as catalysts. Compound 8 was synthesized through the reaction of (iPrPNHP)Fe(H)(CO)(PF6) (6) with H2, and the solid-state structure was established using both X-ray and neutron diffraction. As part of our studies on understanding the reactivity of 5-L, we determined the thermodynamic hydricity of 2, which is valuable for predicting its reactivity as a hydride donor. Further, it is shown that species such as 5-L decompose to the same inactive species observed in catalysis using 1 and 2, and theoretical calculations suggest that this likely occurs via a bimolecular pathway. To provide support for this hypothesis, we isolated the dimeric species [{(iPrPNHP)Fe(H)(CO)}2{μ-CN}]+ (11) andmore »
- Authors:
-
- Yale Univ., New Haven, CT (United States). Dept. of Chemistry
- Univ. of Missouri, Columbia, MO (United States). Dept. of Chemistry
- Brookhaven National Lab. (BNL), Upton, NY (United States). Chemistry Division
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Neutron Scattering Division
- Publication Date:
- Research Org.:
- Brookhaven National Lab. (BNL), Upton, NY (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division; National Science Foundation (NSF)
- OSTI Identifier:
- 1821209
- Report Number(s):
- BNL-222122-2021-JAAM
Journal ID: ISSN 2155-5435
- Grant/Contract Number:
- SC0012704; SC0018222
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ACS Catalysis
- Additional Journal Information:
- Journal Volume: 11; Journal Issue: 16; 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; iron; transition-metal catalysis; catalyst decomposition; pincer ligands; reaction mechanism; formic acid; dehydrogenation
Citation Formats
Curley, Julia B., Smith, Nicholas E., Bernskoetter, Wesley H., Ertem, Mehmed Z., Hazari, Nilay, Mercado, Brandon Q., Townsend, Tanya M., and Wang, Xiaoping. Understanding the Reactivity and Decomposition of a Highly Active Iron Pincer Catalyst for Hydrogenation and Dehydrogenation Reactions. United States: N. p., 2021.
Web. doi:10.1021/acscatal.1c03347.
Curley, Julia B., Smith, Nicholas E., Bernskoetter, Wesley H., Ertem, Mehmed Z., Hazari, Nilay, Mercado, Brandon Q., Townsend, Tanya M., & Wang, Xiaoping. Understanding the Reactivity and Decomposition of a Highly Active Iron Pincer Catalyst for Hydrogenation and Dehydrogenation Reactions. United States. https://doi.org/10.1021/acscatal.1c03347
Curley, Julia B., Smith, Nicholas E., Bernskoetter, Wesley H., Ertem, Mehmed Z., Hazari, Nilay, Mercado, Brandon Q., Townsend, Tanya M., and Wang, Xiaoping. Wed .
"Understanding the Reactivity and Decomposition of a Highly Active Iron Pincer Catalyst for Hydrogenation and Dehydrogenation Reactions". United States. https://doi.org/10.1021/acscatal.1c03347. https://www.osti.gov/servlets/purl/1821209.
@article{osti_1821209,
title = {Understanding the Reactivity and Decomposition of a Highly Active Iron Pincer Catalyst for Hydrogenation and Dehydrogenation Reactions},
author = {Curley, Julia B. and Smith, Nicholas E. and Bernskoetter, Wesley H. and Ertem, Mehmed Z. and Hazari, Nilay and Mercado, Brandon Q. and Townsend, Tanya M. and Wang, Xiaoping},
abstractNote = {The iron pincer complex (iPrPNP)Fe(H)(CO) (1, iPrPNP– = N(CH2CH2PiPr2)2-) is an active (pre)catalyst for many hydrogenation and dehydrogenation reactions. This is in part because 1 can reversibly add H2 across the iron-amide bond to form (iPrPNHP)Fe(H)2(CO) (2, iPrPNHP = HN(CH2CH2PiPr2)2). However, rapid decomposition limits the catalytic performance of 1 and related complexes. We explored the pathways through which catalytic intermediates related to 1 and 2 undergo decomposition. This involved characterizing the unstable and previously unobserved complexes [(iPrPNHP)Fe(H)(CO)(L)]+ (5-L; L = THF or N2) and [(iPrPNHP)Fe(H)(H2)(CO)]+ (8), which are proposed as intermediates when 1 and 2 are used as catalysts. Compound 8 was synthesized through the reaction of (iPrPNHP)Fe(H)(CO)(PF6) (6) with H2, and the solid-state structure was established using both X-ray and neutron diffraction. As part of our studies on understanding the reactivity of 5-L, we determined the thermodynamic hydricity of 2, which is valuable for predicting its reactivity as a hydride donor. Further, it is shown that species such as 5-L decompose to the same inactive species observed in catalysis using 1 and 2, and theoretical calculations suggest that this likely occurs via a bimolecular pathway. To provide support for this hypothesis, we isolated the dimeric species [{(iPrPNHP)Fe(H)(CO)}2{μ-CN}]+ (11) and [{(iPrPNHP)Fe(H)(CO)}2{μ-OC(H)O}]+ (12), which show that catalytic intermediates ligated by iPrPNHP can form dimeric species. Our results provide general strategies for improving catalysis using 1 and 2, and we used this information to rationally increase the performance of 1 in formic acid dehydrogenation.},
doi = {10.1021/acscatal.1c03347},
journal = {ACS Catalysis},
number = 16,
volume = 11,
place = {United States},
year = {Wed Aug 11 00:00:00 EDT 2021},
month = {Wed Aug 11 00:00:00 EDT 2021}
}
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