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Title: Mesoporous Silica-Supported Amidozirconium-Catalyzed Carbonyl Hydroboration

Abstract

The hydroboration of aldehydes and ketones using a silica-supported zirconium catalyst is reported. Reaction of Zr(NMe2)4 and mesoporous silica nanoparticles (MSN) provides the catalytic material Zr(NMe2)n@MSN. Exhaustive characterization of Zr(NMe2)n@MSN with solid-state (SS)NMR and infrared spectroscopy, as well as through reactivity studies, suggests its surface structure is primarily ≡SiOZr(NMe2)3. The presence of these nitrogen-containing zirconium sites is supported by 15N NMR spectroscopy, including natural abundance 15N NMR measurements using dynamic nuclear polarization (DNP) SSNMR. The Zr(NMe2)n@MSN material reacts with pinacolborane (HBpin) to provide Me2NBpin and the material ZrH/Bpin@MSN that is composed of interacting surface-bonded zirconium hydride and surface-bonded borane ≡SiOBpin moieties in an approximately 1:1 ratio, as well as zirconium sites coordinated by dimethylamine. The ZrH/Bpin@MSN is characterized by 1H/2H and 11B SSNMR and infrared spectroscopy and through its reactivity with D2. The zirconium hydride material or the zirconium amide precursor Zr(NMe2)n@MSN catalyzes the selective hydroboration of aldehydes and ketones with HBpin in the presence of functional groups that are often reduced under hydroboration conditions or are sensitive to metal hydrides, including olefins, alkynes, nitro groups, halides, and ethers. Remarkably, this catalytic material may be recycled without loss of activity at least eight times, and air-exposed materials are catalytically active.more » These supported zirconium centers are robust catalytic sites for carbonyl reduction and that surface-supported, catalytically reactive zirconium hydride may be generated from zirconium-amide or zirconium alkoxide sites.« less

Authors:
 [1];  [1];  [1];  [1];  [1];  [1];  [1];  [1];  [1]
  1. Iowa State Univ., Ames, IA (United States)
Publication Date:
Research Org.:
Ames Lab., Ames, IA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1226905
Report Number(s):
IS-J-8514
Journal ID: ISSN 2155-5435
Grant/Contract Number:  
AC02-07CH11358
Resource Type:
Accepted Manuscript
Journal Name:
ACS Catalysis
Additional Journal Information:
Journal Volume: 2015; Journal Issue: 5; 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; single-site catalysts; carbonyl hydroboration; zirconium hydride; interfacial catalysis; mesoporous silica; solid-state NMR

Citation Formats

Eedugurala, Naresh, Wang, Zhuoran, Chaudhary, Umesh, Nelson, Nicholas, Kandel, Kapil, Kobayashi, Takeshi, Slowing, Igor I., Pruski, Marek, and Sadow, Aaron D.. Mesoporous Silica-Supported Amidozirconium-Catalyzed Carbonyl Hydroboration. United States: N. p., 2015. Web. https://doi.org/10.1021/acscatal.5b01671.
Eedugurala, Naresh, Wang, Zhuoran, Chaudhary, Umesh, Nelson, Nicholas, Kandel, Kapil, Kobayashi, Takeshi, Slowing, Igor I., Pruski, Marek, & Sadow, Aaron D.. Mesoporous Silica-Supported Amidozirconium-Catalyzed Carbonyl Hydroboration. United States. https://doi.org/10.1021/acscatal.5b01671
Eedugurala, Naresh, Wang, Zhuoran, Chaudhary, Umesh, Nelson, Nicholas, Kandel, Kapil, Kobayashi, Takeshi, Slowing, Igor I., Pruski, Marek, and Sadow, Aaron D.. Wed . "Mesoporous Silica-Supported Amidozirconium-Catalyzed Carbonyl Hydroboration". United States. https://doi.org/10.1021/acscatal.5b01671. https://www.osti.gov/servlets/purl/1226905.
@article{osti_1226905,
title = {Mesoporous Silica-Supported Amidozirconium-Catalyzed Carbonyl Hydroboration},
author = {Eedugurala, Naresh and Wang, Zhuoran and Chaudhary, Umesh and Nelson, Nicholas and Kandel, Kapil and Kobayashi, Takeshi and Slowing, Igor I. and Pruski, Marek and Sadow, Aaron D.},
abstractNote = {The hydroboration of aldehydes and ketones using a silica-supported zirconium catalyst is reported. Reaction of Zr(NMe2)4 and mesoporous silica nanoparticles (MSN) provides the catalytic material Zr(NMe2)n@MSN. Exhaustive characterization of Zr(NMe2)n@MSN with solid-state (SS)NMR and infrared spectroscopy, as well as through reactivity studies, suggests its surface structure is primarily ≡SiOZr(NMe2)3. The presence of these nitrogen-containing zirconium sites is supported by 15N NMR spectroscopy, including natural abundance 15N NMR measurements using dynamic nuclear polarization (DNP) SSNMR. The Zr(NMe2)n@MSN material reacts with pinacolborane (HBpin) to provide Me2NBpin and the material ZrH/Bpin@MSN that is composed of interacting surface-bonded zirconium hydride and surface-bonded borane ≡SiOBpin moieties in an approximately 1:1 ratio, as well as zirconium sites coordinated by dimethylamine. The ZrH/Bpin@MSN is characterized by 1H/2H and 11B SSNMR and infrared spectroscopy and through its reactivity with D2. The zirconium hydride material or the zirconium amide precursor Zr(NMe2)n@MSN catalyzes the selective hydroboration of aldehydes and ketones with HBpin in the presence of functional groups that are often reduced under hydroboration conditions or are sensitive to metal hydrides, including olefins, alkynes, nitro groups, halides, and ethers. Remarkably, this catalytic material may be recycled without loss of activity at least eight times, and air-exposed materials are catalytically active. These supported zirconium centers are robust catalytic sites for carbonyl reduction and that surface-supported, catalytically reactive zirconium hydride may be generated from zirconium-amide or zirconium alkoxide sites.},
doi = {10.1021/acscatal.5b01671},
journal = {ACS Catalysis},
number = 5,
volume = 2015,
place = {United States},
year = {2015},
month = {11}
}

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