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Al/N-based active Lewis pairs: isocyanate insertion products as efficient nucleophiles employed for the facile generation of highly functional molecules

  • Julia Silissa Horstmann , Alexander Hepp , Marcus Layh and Werner Uhl EMAIL logo
Published/Copyright: July 6, 2020
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 75 Issue 6-7

Abstract

The previously reported active Lewis pair (ALP) iBu2Al–N(2-Ad)NC5H10 (1) (2-Ad = 2-adamantyl) is readily accessible by hydroalumination of the hydrazone H10C5N–N=(2-C10H14) with H–AliBu2. Treatment of 1 with two equivalents of isocyanates R-N=C=O yields six-membered AlC2N2O heterocycles 2 (2a, R = Ph; 2b, R = p-Tol) by dual insertion into the Al–N bonds. 2a reacts as a nucleophile with carboxylic acid chlorides R-C(O)–Cl [R = CH2tBu, p-Tol, H2CCH(Me)C6H4(4-CH2CHMe2) (Ibu-profen acid chloride), 0.5 (1,4-C6H4)] to afford by elimination of iBu2AlCl and hydrolysis new triuret derivatives R-C(O)[N(Ph)C(O)]2–N(2-Ad)NC5H10 (3a to 3d) as colourless, sparingly soluble solids in moderate (3c) to high (3b) yields. The analogous reaction of 2a with (p-Tol)–C(Cl)=N(p-Tol) leads to the imidoyl derivative (p-Tol)N=C(p-Tol)[N(Ph)C(O)]2–N(2-Ad)NC5H10 (4a), which showed a fast exchange of phenyl and tolyl groups to yield a mixture of isomers. The analogous reaction of 2b affords the corresponding compound 4b for which a single isomer is isolated despite the scrambling of substituents.

Keywords: activation; active Lewis pairs; aluminum; nucleophiles; triurets
Corresponding author: Werner Uhl, Institut für Anorganische und Analytische Chemie, Universität Münster, Corrensstraße 30, 48149 Münster, Germany, E-mail:

Funding source: Deutsche Forschungsgemeinschaft, Germany

Acknowledgements

We are grateful to the Deutsche Forschungsgemeinschaft (SFB 858) for generous financial support.

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This research was funded by the Deutsche Forschungsgemeinschaft (SFB 858).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Supplementary material

The online version of this article offers supplementary material https://doi.org/10.1515/znb-2020-0049.

Received: 2020-04-16
Accepted: 2020-04-28
Published Online: 2020-07-06
Published in Print: 2020-08-27

© 2020 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research articles
  4. Derivatives of the triaminoguanidinium ion, 7: unsymmetrically substituted N,N',N''-triaminoguanidinium salts via a cyclopentanone spiroaminal intermediate
  5. Diethyl (iodoethynyl)phosphonate and (iodoethynyl)diphenylphosphane oxide: crystal structures and some cycloaddition reactions
  6. Synthesis, molecular structure and BSA-binding properties of a new binuclear Cd(II) complex based on 2-(1H-tetrazol-1-methyl)-1H-imidazole-4,5-dicarboxylic acid
  7. Microwave synthesis of a blue luminescent silver(I) coordination polymer with a rigid tris-triazole ligand
  8. Single-crystal structure determination of LaNi5–xInx and LaNi9–xIn2+x
  9. The reaction of imidazo[1,5-a]pyridines with ninhydrin revisited
  10. The syntheses, structures, and magnetic properties of two mononuclear manganese(II) complexes involving in situ hydrothermal decarboxylation
  11. A cobalt(II) coordination polymer constructed with the 2-carboxy-phenoxyacetate linker showing a corrugated layer structure: synthesis, structure analysis and magnetic properties
  12. Hexaniobate anions connected by [Ni(cyclam)]2+ complexes yield two interpenetrating three-dimensional networks
  13. High-pressure synthesis and crystal structure of the samarium meta-oxoborate γ-Sm(BO2)3
  14. High-pressure synthesis and characterization of the non-centrosymmetric scandium borate ScB6O9(OH)3
  15. Al5B12O25(OH) and Ga4InB12O25(OH) – two additional triel borates with the structure type M5B12O25(OH) (M = Ga, In)
  16. Al/N-based active Lewis pairs: isocyanate insertion products as efficient nucleophiles employed for the facile generation of highly functional molecules
  17. New compounds of the Li2MSn3S8 type
  18. Synthesis and magnetic properties of the extended RE4Pd9Al24 series (RE = Sc, Y, Ce–Nd, Sm, Gd–Lu)
  19. Solid solutions EuAu4Cd2−xMgx with a remarkably stable ferromagnetic ground state
  20. Mechanistic investigations on C–H activated dealkylating cyclo-amination reactions of substituted triazenes, formamidines and amidines
  21. Orthoamide und Iminiumsalze, IIC. Darstellung von N-(ω-Ammonioalkyl)-N,N′,N′,N″,N″-peralkylierten Guanidiniumsalzen und N-(ω-Aminoalkyl)-N′,N′,N″,N″-tetramethylguanidinen
  22. Orthoamide und Iminiumsalze, IC. Synthese und Reaktionen von N,N,N′,N′,N′′-Pentaalkyl-N′′-[2-(N,N,N′,N′,N′′-pentaalkylguanidinio)ethyl]-guanidiniumsalzen
  23. Orthoamide und Iminiumsalze, C. Vinyloge Guanidiniumsalz-basierte ionische Flüssigkeiten sowie phenyloge Guanidiniumsalze und Orthoamide
  24. Notes
  25. La5Ir1.73In4.27 with Lu5Ni2In4-type structure
  26. The scandium-rich indide Sc50Pt13.47In2.53
https://doi.org/10.1515/znb-2020-0049
Keywords for this article
activation; active Lewis pairs; aluminum; nucleophiles; triurets

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research articles
  4. Derivatives of the triaminoguanidinium ion, 7: unsymmetrically substituted N,N',N''-triaminoguanidinium salts via a cyclopentanone spiroaminal intermediate
  5. Diethyl (iodoethynyl)phosphonate and (iodoethynyl)diphenylphosphane oxide: crystal structures and some cycloaddition reactions
  6. Synthesis, molecular structure and BSA-binding properties of a new binuclear Cd(II) complex based on 2-(1H-tetrazol-1-methyl)-1H-imidazole-4,5-dicarboxylic acid
  7. Microwave synthesis of a blue luminescent silver(I) coordination polymer with a rigid tris-triazole ligand
  8. Single-crystal structure determination of LaNi5–xInx and LaNi9–xIn2+x
  9. The reaction of imidazo[1,5-a]pyridines with ninhydrin revisited
  10. The syntheses, structures, and magnetic properties of two mononuclear manganese(II) complexes involving in situ hydrothermal decarboxylation
  11. A cobalt(II) coordination polymer constructed with the 2-carboxy-phenoxyacetate linker showing a corrugated layer structure: synthesis, structure analysis and magnetic properties
  12. Hexaniobate anions connected by [Ni(cyclam)]2+ complexes yield two interpenetrating three-dimensional networks
  13. High-pressure synthesis and crystal structure of the samarium meta-oxoborate γ-Sm(BO2)3
  14. High-pressure synthesis and characterization of the non-centrosymmetric scandium borate ScB6O9(OH)3
  15. Al5B12O25(OH) and Ga4InB12O25(OH) – two additional triel borates with the structure type M5B12O25(OH) (M = Ga, In)
  16. Al/N-based active Lewis pairs: isocyanate insertion products as efficient nucleophiles employed for the facile generation of highly functional molecules
  17. New compounds of the Li2MSn3S8 type
  18. Synthesis and magnetic properties of the extended RE4Pd9Al24 series (RE = Sc, Y, Ce–Nd, Sm, Gd–Lu)
  19. Solid solutions EuAu4Cd2−xMgx with a remarkably stable ferromagnetic ground state
  20. Mechanistic investigations on C–H activated dealkylating cyclo-amination reactions of substituted triazenes, formamidines and amidines
  21. Orthoamide und Iminiumsalze, IIC. Darstellung von N-(ω-Ammonioalkyl)-N,N′,N′,N″,N″-peralkylierten Guanidiniumsalzen und N-(ω-Aminoalkyl)-N′,N′,N″,N″-tetramethylguanidinen
  22. Orthoamide und Iminiumsalze, IC. Synthese und Reaktionen von N,N,N′,N′,N′′-Pentaalkyl-N′′-[2-(N,N,N′,N′,N′′-pentaalkylguanidinio)ethyl]-guanidiniumsalzen
  23. Orthoamide und Iminiumsalze, C. Vinyloge Guanidiniumsalz-basierte ionische Flüssigkeiten sowie phenyloge Guanidiniumsalze und Orthoamide
  24. Notes
  25. La5Ir1.73In4.27 with Lu5Ni2In4-type structure
  26. The scandium-rich indide Sc50Pt13.47In2.53
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