1,2-Addition and cycloaddition reactions of niobium bis(imido) and oxo imido complexes
Abstract
The bis(imido) complexes (BDI)Nb(NtBu)2 and (BDI)Nb(NtBu)(NAr) (BDI = N,N'-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate; Ar = 2,6-diisopropylphenyl) were shown to engage in 1,2-addition and [2 + 2] cycloaddition reactions with a wide variety of substrates. Reaction of the bis(imido) complexes with dihydrogen, silanes, and boranes yielded hydrido-amido-imido complexes via 1,2-addition across Nb-imido π-bonds; some of these complexes were shown to further react via insertion of carbon dioxide to give formate-amido-imido products. Similarly, reaction of (BDI)Nb(NtBu)2 with tert-butylacetylene yielded an acetylide-amido-imido complex. In contrast to these results, many related mono(imido) Nb BDI complexes do not exhibit 1,2-addition reactivity, suggesting that π-loading plays an important role in activating the Nb–N π-bonds toward addition. The same bis(imido) complexes were also shown to engage in [2 + 2] cycloaddition reactions with oxygen- and sulfur-containing heteroallenes to give carbamate- and thiocarbamate-imido complexes: some of these complexes readily dimerized to give bis-μ-sulfido, bis-μ-iminodicarboxylate, and bis-μ-carbonate complexes. The mononuclear carbamate imido complex (BDI)Nb(NAr)(N(tBu)CO2) (12) could be induced to eject tert-butylisocyanate to generate a four-coordinate terminal oxo imido intermediate, which could be trapped as the five-coordinate pyridine or DMAP adduct. The DMAP adducted oxo imido complex (BDI)NbO(NAr)(DMAP) (16) was shown to engage in 1,2-addition of silanes across the Nb-oxo π-bond; this represents amore »
- Authors:
-
[1];
[1];
[1];
[2];
[1];
[2]
- Department of Chemistry, University of California, Berkeley, USA
- Department of Chemistry, University of California, Berkeley, USA, Chemical Sciences Division
- Publication Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC); National Science Foundation (NSF); US Air Force Office of Scientific Research (AFOSR); National Institutes of Health (NIH)
- OSTI Identifier:
- 1671349
- Alternate Identifier(s):
- OSTI ID: 1763681
- Grant/Contract Number:
- AC02-05CH11231; CHE-1465188; 1954612; FA9550-11-1-0008; DGE 1752814; S10-RR027172
- Resource Type:
- Published Article
- Journal Name:
- Chemical Science
- Additional Journal Information:
- Journal Name: Chemical Science Journal Volume: 11 Journal Issue: 42; Journal ID: ISSN 2041-6520
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United Kingdom
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Fostvedt, Jade I., Grant, Lauren N., Kriegel, Benjamin M., Obenhuber, Andreas H., Lohrey, Trevor D., Bergman, Robert G., and Arnold, John. 1,2-Addition and cycloaddition reactions of niobium bis(imido) and oxo imido complexes. United Kingdom: N. p., 2020.
Web. doi:10.1039/D0SC03489D.
Fostvedt, Jade I., Grant, Lauren N., Kriegel, Benjamin M., Obenhuber, Andreas H., Lohrey, Trevor D., Bergman, Robert G., & Arnold, John. 1,2-Addition and cycloaddition reactions of niobium bis(imido) and oxo imido complexes. United Kingdom. https://doi.org/10.1039/D0SC03489D
Fostvedt, Jade I., Grant, Lauren N., Kriegel, Benjamin M., Obenhuber, Andreas H., Lohrey, Trevor D., Bergman, Robert G., and Arnold, John. Wed .
"1,2-Addition and cycloaddition reactions of niobium bis(imido) and oxo imido complexes". United Kingdom. https://doi.org/10.1039/D0SC03489D.
@article{osti_1671349,
title = {1,2-Addition and cycloaddition reactions of niobium bis(imido) and oxo imido complexes},
author = {Fostvedt, Jade I. and Grant, Lauren N. and Kriegel, Benjamin M. and Obenhuber, Andreas H. and Lohrey, Trevor D. and Bergman, Robert G. and Arnold, John},
abstractNote = {The bis(imido) complexes (BDI)Nb(NtBu)2 and (BDI)Nb(NtBu)(NAr) (BDI = N,N'-bis(2,6-diisopropylphenyl)-3,5-dimethyl-β-diketiminate; Ar = 2,6-diisopropylphenyl) were shown to engage in 1,2-addition and [2 + 2] cycloaddition reactions with a wide variety of substrates. Reaction of the bis(imido) complexes with dihydrogen, silanes, and boranes yielded hydrido-amido-imido complexes via 1,2-addition across Nb-imido π-bonds; some of these complexes were shown to further react via insertion of carbon dioxide to give formate-amido-imido products. Similarly, reaction of (BDI)Nb(NtBu)2 with tert-butylacetylene yielded an acetylide-amido-imido complex. In contrast to these results, many related mono(imido) Nb BDI complexes do not exhibit 1,2-addition reactivity, suggesting that π-loading plays an important role in activating the Nb–N π-bonds toward addition. The same bis(imido) complexes were also shown to engage in [2 + 2] cycloaddition reactions with oxygen- and sulfur-containing heteroallenes to give carbamate- and thiocarbamate-imido complexes: some of these complexes readily dimerized to give bis-μ-sulfido, bis-μ-iminodicarboxylate, and bis-μ-carbonate complexes. The mononuclear carbamate imido complex (BDI)Nb(NAr)(N(tBu)CO2) (12) could be induced to eject tert-butylisocyanate to generate a four-coordinate terminal oxo imido intermediate, which could be trapped as the five-coordinate pyridine or DMAP adduct. The DMAP adducted oxo imido complex (BDI)NbO(NAr)(DMAP) (16) was shown to engage in 1,2-addition of silanes across the Nb-oxo π-bond; this represents a new reaction pathway in group 5 chemistry.},
doi = {10.1039/D0SC03489D},
journal = {Chemical Science},
number = 42,
volume = 11,
place = {United Kingdom},
year = {2020},
month = {11}
}
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