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Title: Electrophilic Organoiridium(III) Pincer Complexes on Sulfated Zirconia for Hydrocarbon Activation and Functionalization

Abstract

Single-site supported organometallic catalysts bring together the favorable aspects of homogeneous and heterogeneous catalysis while offering opportunities to investigate the impact of metal-support interactions on reactivity. We report a (dmPhebox)Ir(III) (dmPhebox = 2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl) complex chemisorbed on sulfated zirconia, the molecular precursor for which was previously applied to hydrocarbon functionalization. Spectroscopic methods such as diffuse reflectance infrared Fourier transformation spectroscopy (DRIFTS), dynamic nuclear polarization (DNP)-enhanced solid-state nuclear magnetic resonance (SSNMR) spectroscopy, and X-ray absorption spectroscopy (XAS) were used to characterize the supported species. Tetrabutylammonium acetate was found to remove the organometallic species from the surface, enabling solution-phase analytical techniques in conjunction with traditional surface methods. Cationic character was imparted to the iridium center by its grafting onto sulfated zirconia, imbuing high levels of activity in electrophilic C–H bond functionalization reactions such as the stoichiometric dehydrogenation of alkanes, with density functional theory (DFT) calculations showing a lower barrier for β–H elimination. Catalytic hydrogenation of olefins was also facilitated by the sulfated zirconia-supported (dmPhebox)Ir(III) complex, while the homologous complex on silica was inactive under comparable conditions.

Authors:
 [1]; ORCiD logo [1];  [2]; ORCiD logo [3];  [1];  [1];  [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [4]; ORCiD logo [1]
  1. Argonne National Lab. (ANL), Lemont, IL (United States)
  2. Ames Lab., Ames, IA (United States)
  3. Ames Lab. and Iowa State Univ., Ames, IA (United States)
  4. Univ. of Pennsylvania, Philadelphia, PA (United States)
Publication Date:
Research Org.:
Ames Laboratory (AMES), Ames, IA (United States); Argonne National Laboratory (ANL), Argonne, IL (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Workforce Development for Teachers and Scientists (WDTS)
OSTI Identifier:
1509486
Alternate Identifier(s):
OSTI ID: 1532537; OSTI ID: 1542882
Report Number(s):
IS-J-9872
Journal ID: ISSN 0002-7863
Grant/Contract Number:  
AC02-06CH11357; AC02-07CH11358; AC-02-06CH11357; AC-02-07CH11358
Resource Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 141; Journal Issue: 15; 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; electrophilic activation; hydrocarbon functionalization; pincer; sulfated oxides; surface organometallic chemistry

Citation Formats

Syed, Zoha H., Kaphan, David M., Perras, Frédéric A., Pruski, Marek, Ferrandon, Magali S., Wegener, Evan C., Celik, Gokhan, Wen, Jianguo, Liu, Cong, Dogan, Fulya, Goldberg, Karen I., and Delferro, Massimiliano. Electrophilic Organoiridium(III) Pincer Complexes on Sulfated Zirconia for Hydrocarbon Activation and Functionalization. United States: N. p., 2019. Web. doi:10.1021/jacs.9b00896.
Syed, Zoha H., Kaphan, David M., Perras, Frédéric A., Pruski, Marek, Ferrandon, Magali S., Wegener, Evan C., Celik, Gokhan, Wen, Jianguo, Liu, Cong, Dogan, Fulya, Goldberg, Karen I., & Delferro, Massimiliano. Electrophilic Organoiridium(III) Pincer Complexes on Sulfated Zirconia for Hydrocarbon Activation and Functionalization. United States. https://doi.org/10.1021/jacs.9b00896
Syed, Zoha H., Kaphan, David M., Perras, Frédéric A., Pruski, Marek, Ferrandon, Magali S., Wegener, Evan C., Celik, Gokhan, Wen, Jianguo, Liu, Cong, Dogan, Fulya, Goldberg, Karen I., and Delferro, Massimiliano. Mon . "Electrophilic Organoiridium(III) Pincer Complexes on Sulfated Zirconia for Hydrocarbon Activation and Functionalization". United States. https://doi.org/10.1021/jacs.9b00896. https://www.osti.gov/servlets/purl/1509486.
@article{osti_1509486,
title = {Electrophilic Organoiridium(III) Pincer Complexes on Sulfated Zirconia for Hydrocarbon Activation and Functionalization},
author = {Syed, Zoha H. and Kaphan, David M. and Perras, Frédéric A. and Pruski, Marek and Ferrandon, Magali S. and Wegener, Evan C. and Celik, Gokhan and Wen, Jianguo and Liu, Cong and Dogan, Fulya and Goldberg, Karen I. and Delferro, Massimiliano},
abstractNote = {Single-site supported organometallic catalysts bring together the favorable aspects of homogeneous and heterogeneous catalysis while offering opportunities to investigate the impact of metal-support interactions on reactivity. We report a (dmPhebox)Ir(III) (dmPhebox = 2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl) complex chemisorbed on sulfated zirconia, the molecular precursor for which was previously applied to hydrocarbon functionalization. Spectroscopic methods such as diffuse reflectance infrared Fourier transformation spectroscopy (DRIFTS), dynamic nuclear polarization (DNP)-enhanced solid-state nuclear magnetic resonance (SSNMR) spectroscopy, and X-ray absorption spectroscopy (XAS) were used to characterize the supported species. Tetrabutylammonium acetate was found to remove the organometallic species from the surface, enabling solution-phase analytical techniques in conjunction with traditional surface methods. Cationic character was imparted to the iridium center by its grafting onto sulfated zirconia, imbuing high levels of activity in electrophilic C–H bond functionalization reactions such as the stoichiometric dehydrogenation of alkanes, with density functional theory (DFT) calculations showing a lower barrier for β–H elimination. Catalytic hydrogenation of olefins was also facilitated by the sulfated zirconia-supported (dmPhebox)Ir(III) complex, while the homologous complex on silica was inactive under comparable conditions.},
doi = {10.1021/jacs.9b00896},
journal = {Journal of the American Chemical Society},
number = 15,
volume = 141,
place = {United States},
year = {Mon Apr 22 00:00:00 EDT 2019},
month = {Mon Apr 22 00:00:00 EDT 2019}
}

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Works referencing / citing this record:

Alkane isomerization over sulfated zirconia solid acid system
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  • Wang, Pengzhao; Yue, Yuanyuan; Wang, Tinghai
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