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Title: Chemoselective Hydrogenation with Supported Organoplatinum(IV) Catalyst on Zn(II)-Modified Silica

Abstract

Well-defined organoplatinum(IV) sites were grafted on a Zn(II)-modified SiO2 support via surface organometallic chemistry in toluene at room temperature. Solid-state spectroscopies including XAS, DRIFTS, DRUV-Vis, and solid-state (SS)NMR enhanced by dynamic nuclear polarization (DNP), as well as TPR-H2 and TEM techniques revealed highly dispersed (methylcyclopentadi-enyl)methylplatinum(IV) sites on the surface ((MeCp)PtMe/Zn/SiO2, 1). In addition, computational modelling suggests that the surface reaction of (MeCp)PtMe3 with Zn(II)-modified SiO2 support is thermodynamically favorable (ΔG = -12.4 kcal/mol), likely due to the increased acidity of the hydroxyl group, as confirmed by NH3-TPD and DNP-enhanced 17O{1H} SSNMR. In situ DRIFTS and XAS hydrogenation experiments reveal the formation of a surface Pt(IV)-H upon hydrogenolysis of Pt-Me groups. The heterogenized organoplatinum(IV)-H sites catalyze the selective partial hydrogenation of 1,3-butadiene to butenes (up to 95%) and the reduction of nitrobenzene derivatives to anilines (up to 100%) with excellent tolerance of reduction-sensitive func-tional groups (olefin, carbonyl, nitrile, halogens) under mild reaction conditions.

Authors:
ORCiD logo [1];  [1];  [1];  [1]; ORCiD logo [1];  [2];  [3]; ORCiD logo [4];  [5]; ORCiD logo [1]
+ Show Author Affiliations
  1. Argonne National Lab. (ANL), Lemont, IL (United States). Chemical Sciences and Engineering Division
  2. Argonne National Lab. (ANL), Lemont, IL (United States). Energy Sciences Division
  3. Ames Lab., Ames, IA (United States)
  4. Ames Lab., Ames, IA (United States); Iowa State Univ., Ames, IA (United States). Department of Chemistry
  5. Argonne National Lab. (ANL), Lemont, IL (United States). Chemical Sciences and Engineering Division ; Northwestern Univ., Evanston, IL (United States). Department of Chemistry
Publication Date:
Research Org.:
Ames Lab., Ames, IA (United States); Argonne National Lab. (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division
OSTI Identifier:
1427735
Alternate Identifier(s):
OSTI ID: 1435048
Report Number(s):
IS-J-9598
Journal ID: ISSN 0002-7863; TRN: US1802467
Grant/Contract Number:  
AC02-06CH11357; AC02-07CH11358
Resource Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 140; Journal Issue: 11; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; atomic layer deposition; chemoselectivity; hydrogenation; platinum; supported organometallic catalysis

Citation Formats

Camacho-Bunquin, Jeffrey, Ferrandon, Magali, Sohn, Hyuntae, Yang, Dali, Liu, Cong, Ignacio-de Leon, Patricia Anne, Perras, Frédéric A., Pruski, Marek, Stair, Peter C., and Delferro, Massimiliano. Chemoselective Hydrogenation with Supported Organoplatinum(IV) Catalyst on Zn(II)-Modified Silica. United States: N. p., 2018. Web. doi:10.1021/jacs.7b11981.
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Camacho-Bunquin, Jeffrey, Ferrandon, Magali, Sohn, Hyuntae, Yang, Dali, Liu, Cong, Ignacio-de Leon, Patricia Anne, Perras, Frédéric A., Pruski, Marek, Stair, Peter C., & Delferro, Massimiliano. Chemoselective Hydrogenation with Supported Organoplatinum(IV) Catalyst on Zn(II)-Modified Silica. United States. https://doi.org/10.1021/jacs.7b11981
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Camacho-Bunquin, Jeffrey, Ferrandon, Magali, Sohn, Hyuntae, Yang, Dali, Liu, Cong, Ignacio-de Leon, Patricia Anne, Perras, Frédéric A., Pruski, Marek, Stair, Peter C., and Delferro, Massimiliano. Tue . "Chemoselective Hydrogenation with Supported Organoplatinum(IV) Catalyst on Zn(II)-Modified Silica". United States. https://doi.org/10.1021/jacs.7b11981. https://www.osti.gov/servlets/purl/1427735.
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@article{osti_1427735,
title = {Chemoselective Hydrogenation with Supported Organoplatinum(IV) Catalyst on Zn(II)-Modified Silica},
author = {Camacho-Bunquin, Jeffrey and Ferrandon, Magali and Sohn, Hyuntae and Yang, Dali and Liu, Cong and Ignacio-de Leon, Patricia Anne and Perras, Frédéric A. and Pruski, Marek and Stair, Peter C. and Delferro, Massimiliano},
abstractNote = {Well-defined organoplatinum(IV) sites were grafted on a Zn(II)-modified SiO2 support via surface organometallic chemistry in toluene at room temperature. Solid-state spectroscopies including XAS, DRIFTS, DRUV-Vis, and solid-state (SS)NMR enhanced by dynamic nuclear polarization (DNP), as well as TPR-H2 and TEM techniques revealed highly dispersed (methylcyclopentadi-enyl)methylplatinum(IV) sites on the surface ((MeCp)PtMe/Zn/SiO2, 1). In addition, computational modelling suggests that the surface reaction of (MeCp)PtMe3 with Zn(II)-modified SiO2 support is thermodynamically favorable (ΔG = -12.4 kcal/mol), likely due to the increased acidity of the hydroxyl group, as confirmed by NH3-TPD and DNP-enhanced 17O{1H} SSNMR. In situ DRIFTS and XAS hydrogenation experiments reveal the formation of a surface Pt(IV)-H upon hydrogenolysis of Pt-Me groups. The heterogenized organoplatinum(IV)-H sites catalyze the selective partial hydrogenation of 1,3-butadiene to butenes (up to 95%) and the reduction of nitrobenzene derivatives to anilines (up to 100%) with excellent tolerance of reduction-sensitive func-tional groups (olefin, carbonyl, nitrile, halogens) under mild reaction conditions.},
doi = {10.1021/jacs.7b11981},
journal = {Journal of the American Chemical Society},
number = 11,
volume = 140,
place = {United States},
year = {Tue Feb 27 00:00:00 EST 2018},
month = {Tue Feb 27 00:00:00 EST 2018}
}
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Cis dihydride diphosphine complexes of platium(II) and their dehydrogenation to form dimeric platinum(0) complexes. The structure of [Pt(tert-Bu)2P(CH2)3P(tert-Bu)2]2
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Chemistry of Metal Hydrides. I. Reactions of Some Platinum(II) Hydrides
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Stabilizing Single-Atom and Small-Domain Platinum via Combining Organometallic Chemisorption and Atomic Layer Deposition
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Identification of active sites in CO oxidation and water-gas shift over supported Pt catalysts
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A Single-Site Platinum CO Oxidation Catalyst in Zeolite KLTL: Microscopic and Spectroscopic Determination of the Locations of the Platinum Atoms
journal, July 2014

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CO Oxidation on Supported Single Pt Atoms: Experimental and ab Initio Density Functional Studies of CO Interaction with Pt Atom on θ-Al 2 O 3 (010) Surface
journal, August 2013

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  • Journal of the American Chemical Society, Vol. 135, Issue 34
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Platinum species in the pores of NaX, NaY and NaA zeolites studied using EPR, XAS and FTIR spectroscopies
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Particle size effects on the reducibility of titanium dioxide and its relation to the water–gas shift activity of Pt/TiO2 catalysts
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Single-atom catalysis of CO oxidation using Pt1/FeOx
journal, July 2011

  • Qiao, Botao; Wang, Aiqin; Yang, Xiaofeng
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Synthesis and Structural Characterization of an Authentic Platinum(IV) Carbonyl Compound
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Catalysis by Supported Single Metal Atoms
journal, November 2016

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