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Title: The Synthesis, Characterization and Dehydrogenation of Sigma-Complexes of BN-Cyclohexanes

Abstract

The coordination chemistry of the 1,2-BN-cyclohexanes 2,2-R2-1,2-B,N-C4H10 (R2=HH, MeH, Me2) with Ir and Rh metal fragments has been studied. This led to the solution (NMR spectroscopy) and solid-state (X-ray diffraction) characterization of [Ir(PCy3)2(H)2(η2η2-H2BNR2C4H8)][BArF4] (NR2=NH2, NMeH) and [Rh(iPr2PCH2CH2CH2PiPr2)(η2η2-H2BNR2C4H8)][BArF4] (NR2=NH2, NMeH, NMe2). For NR2=NH2 subsequent metal-promoted, dehydrocoupling shows the eventual formation of the cyclic tricyclic borazine [BNC4H8]3, via amino-borane and, tentatively characterized using DFT/GIAO chemical shift calculations, cycloborazane intermediates. For NR2=NMeH the final product is the cyclic amino-borane HBNMeC4H8. The mechanism of dehydrogenation of 2,2-H,Me-1,2-B,N-C4H10 using the {Rh(iPr2PCH2CH2CH2PiPr2)}+ catalyst has been probed. Catalytic experiments indicate the rapid formation of a dimeric species, [Rh2(iPr2PCH2CH2CH2PiPr2)2H5][BArF4]. Using the initial rate method starting from this dimer, a first-order relationship to [amine-borane], but half-order to [Rh] is established, which is suggested to be due to a rapid dimer–monomer equilibrium operating.

Authors:
 [1];  [2];  [1];  [3];  [3];  [2];  [1]
+ Show Author Affiliations
  1. Univ. of Oxford (United Kingdom). Dept. of Chemistry
  2. Boston College, Chestnut Hill, MA (United States). Dept. of Chemistry
  3. Univ. of Alabama, Tuscaloosa, AL (United States). Dept. of Chemistry
Publication Date:
Research Org.:
Boston College, Chestnut Hill, MA (United States); Univ. of Alabama, Tuscaloosa, AL (United States); Univ. of Oxford (United Kingdom)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE); National Inst. of Environmental Health Sciences (NIEHS) (United States); Rhodes Trust (United Kingdom); Engineering and Physical Sciences Research Council (EPSRC)
OSTI Identifier:
1343064
Grant/Contract Number:  
EE0005658; P30 ES00210; EP/M024210; EP/J02127X
Resource Type:
Accepted Manuscript
Journal Name:
Chemistry - A European Journal
Additional Journal Information:
Journal Volume: 22; Journal Issue: 1; Journal ID: ISSN 0947-6539
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; amine-borane; catalysis; iridium; phosphine; rhodium

Citation Formats

Kumar, Amit, Ishibashi, Jacob S. A., Hooper, Thomas N., Mikulas, Tanya C., Dixon, David A., Liu, Shih-Yuan, and Weller, Andrew S. The Synthesis, Characterization and Dehydrogenation of Sigma-Complexes of BN-Cyclohexanes. United States: N. p., 2015. Web. doi:10.1002/chem.201502986.
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Kumar, Amit, Ishibashi, Jacob S. A., Hooper, Thomas N., Mikulas, Tanya C., Dixon, David A., Liu, Shih-Yuan, & Weller, Andrew S. The Synthesis, Characterization and Dehydrogenation of Sigma-Complexes of BN-Cyclohexanes. United States. https://doi.org/10.1002/chem.201502986
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Kumar, Amit, Ishibashi, Jacob S. A., Hooper, Thomas N., Mikulas, Tanya C., Dixon, David A., Liu, Shih-Yuan, and Weller, Andrew S. Wed . "The Synthesis, Characterization and Dehydrogenation of Sigma-Complexes of BN-Cyclohexanes". United States. https://doi.org/10.1002/chem.201502986. https://www.osti.gov/servlets/purl/1343064.
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@article{osti_1343064,
title = {The Synthesis, Characterization and Dehydrogenation of Sigma-Complexes of BN-Cyclohexanes},
author = {Kumar, Amit and Ishibashi, Jacob S. A. and Hooper, Thomas N. and Mikulas, Tanya C. and Dixon, David A. and Liu, Shih-Yuan and Weller, Andrew S.},
abstractNote = {The coordination chemistry of the 1,2-BN-cyclohexanes 2,2-R2-1,2-B,N-C4H10 (R2=HH, MeH, Me2) with Ir and Rh metal fragments has been studied. This led to the solution (NMR spectroscopy) and solid-state (X-ray diffraction) characterization of [Ir(PCy3)2(H)2(η2η2-H2BNR2C4H8)][BArF4] (NR2=NH2, NMeH) and [Rh(iPr2PCH2CH2CH2PiPr2)(η2η2-H2BNR2C4H8)][BArF4] (NR2=NH2, NMeH, NMe2). For NR2=NH2 subsequent metal-promoted, dehydrocoupling shows the eventual formation of the cyclic tricyclic borazine [BNC4H8]3, via amino-borane and, tentatively characterized using DFT/GIAO chemical shift calculations, cycloborazane intermediates. For NR2=NMeH the final product is the cyclic amino-borane HBNMeC4H8. The mechanism of dehydrogenation of 2,2-H,Me-1,2-B,N-C4H10 using the {Rh(iPr2PCH2CH2CH2PiPr2)}+ catalyst has been probed. Catalytic experiments indicate the rapid formation of a dimeric species, [Rh2(iPr2PCH2CH2CH2PiPr2)2H5][BArF4]. Using the initial rate method starting from this dimer, a first-order relationship to [amine-borane], but half-order to [Rh] is established, which is suggested to be due to a rapid dimer–monomer equilibrium operating.},
doi = {10.1002/chem.201502986},
journal = {Chemistry - A European Journal},
number = 1,
volume = 22,
place = {United States},
year = {Wed Nov 25 00:00:00 EST 2015},
month = {Wed Nov 25 00:00:00 EST 2015}
}
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