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Title: 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 » new reaction pathway in group 5 chemistry.« less

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [1];  [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [2]
  1. Department of Chemistry, University of California, Berkeley, USA
  2. 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}
}

Journal Article:
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https://doi.org/10.1039/D0SC03489D

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Novel double substrate insertion versus isocyanate extrusion in reactions of imidotitanium complexes with CO2: critical dependence on imido N-substituents †
journal, January 2001

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Regioselective [2+2] and [4+2] cycloaddition reactivity in an asymmetric niobium(bisimido) moiety towards unsaturated organic molecules
journal, January 2015

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Small Molecule Activation Mediated by a Thorium Terminal Imido Metallocene
journal, July 2015


Direct Hydride/Silyl Exchange— Synthesis and X-ray Study of the Bis(silyl) Complex [Cp2NbH(SiCl3)2]
journal, February 2004

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Carboamination: Additions of Imine CN Bonds Across Alkynes Catalyzed by Imidozirconium Complexes
journal, October 2004

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Zirconium-Mediated Imine Metathesis. Synthesis of 2,4-Diaza-1-zirconiacyclobutanes and the Mechanism of Their Reactions with Imines and Alkynes
journal, March 1994

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Diamination of Olefins: Synthesis, Structures and Reactivity of Osmaimidazolidines
journal, November 2003

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  • Chemistry - A European Journal, Vol. 9, Issue 22
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Catalytic nitrene transfer by a zirconium( iv ) redox-active ligand complex
journal, January 2011

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Variable regiochemistry in the stoichiometric and catalytic hydroamination of alkynes by imidozirconium complexes caused by an unusual dependence of the rate law on alkyne structure and temperature
journal, April 1993

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1,2-Addition versus σ-Bond Metathesis Reactions in Transient Bis(cyclopentadienyl)zirconium Imides: Evidence for a d 0 Dihydrogen Complex
journal, March 2008

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Z -Selective Semihydrogenation of Alkynes Catalyzed by a Cationic Vanadium Bisimido Complex
journal, March 2011

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  • Angewandte Chemie International Edition, Vol. 50, Issue 17
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