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Reactions of a Four‐Membered Borete with Carbon, Silicon, and Gallium Donor Ligands: Fused and Spiro‐Type Boracycles

Donor‐acceptor cyclopropanes or cyclobutanes are dipolar reagents, which are widely used in the synthesis of complex organic (hetero)cycles in ring expansion reactions. Applying this concept to boron containing heterocycles, the four‐membered borete cyclo‐iPr(2)N‐BC(10)H(6) reacted with the carbon d...

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Autores principales: Güven, Zeynep, Denker, Lars, Dolati, Hadi, Wullschläger, Daniela, Trzaskowski, Bartosz, Frank, René
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9322404/
https://www.ncbi.nlm.nih.gov/pubmed/35362629
http://dx.doi.org/10.1002/chem.202200673
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author Güven, Zeynep
Denker, Lars
Dolati, Hadi
Wullschläger, Daniela
Trzaskowski, Bartosz
Frank, René
author_facet Güven, Zeynep
Denker, Lars
Dolati, Hadi
Wullschläger, Daniela
Trzaskowski, Bartosz
Frank, René
author_sort Güven, Zeynep
collection PubMed
description Donor‐acceptor cyclopropanes or cyclobutanes are dipolar reagents, which are widely used in the synthesis of complex organic (hetero)cycles in ring expansion reactions. Applying this concept to boron containing heterocycles, the four‐membered borete cyclo‐iPr(2)N‐BC(10)H(6) reacted with the carbon donor ligands 2,6‐xylylisonitrile and the carbene IMes :C(NMesCH)(2) with ring expansion and ring fusion, respectively. In particular, the tetracyclic structure formed with IMes displays zwitterionic character and absorption in the visible region. In contrast to the carbene IMes, the heavier carbenoids :Si(NDippCH)(2) and :Ga(AmIm) with a two‐coordinate donor atom afford spiro‐type bicyclic compounds, which display four‐coordinate geometry at silicon or gallium. (TD‐)DFT calculations provide deeper insight into the mechanism of formation and the absorption properties of these new compounds.
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spelling pubmed-93224042022-07-30 Reactions of a Four‐Membered Borete with Carbon, Silicon, and Gallium Donor Ligands: Fused and Spiro‐Type Boracycles Güven, Zeynep Denker, Lars Dolati, Hadi Wullschläger, Daniela Trzaskowski, Bartosz Frank, René Chemistry Research Articles Donor‐acceptor cyclopropanes or cyclobutanes are dipolar reagents, which are widely used in the synthesis of complex organic (hetero)cycles in ring expansion reactions. Applying this concept to boron containing heterocycles, the four‐membered borete cyclo‐iPr(2)N‐BC(10)H(6) reacted with the carbon donor ligands 2,6‐xylylisonitrile and the carbene IMes :C(NMesCH)(2) with ring expansion and ring fusion, respectively. In particular, the tetracyclic structure formed with IMes displays zwitterionic character and absorption in the visible region. In contrast to the carbene IMes, the heavier carbenoids :Si(NDippCH)(2) and :Ga(AmIm) with a two‐coordinate donor atom afford spiro‐type bicyclic compounds, which display four‐coordinate geometry at silicon or gallium. (TD‐)DFT calculations provide deeper insight into the mechanism of formation and the absorption properties of these new compounds. John Wiley and Sons Inc. 2022-04-21 2022-06-07 /pmc/articles/PMC9322404/ /pubmed/35362629 http://dx.doi.org/10.1002/chem.202200673 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Güven, Zeynep
Denker, Lars
Dolati, Hadi
Wullschläger, Daniela
Trzaskowski, Bartosz
Frank, René
Reactions of a Four‐Membered Borete with Carbon, Silicon, and Gallium Donor Ligands: Fused and Spiro‐Type Boracycles
title Reactions of a Four‐Membered Borete with Carbon, Silicon, and Gallium Donor Ligands: Fused and Spiro‐Type Boracycles
title_full Reactions of a Four‐Membered Borete with Carbon, Silicon, and Gallium Donor Ligands: Fused and Spiro‐Type Boracycles
title_fullStr Reactions of a Four‐Membered Borete with Carbon, Silicon, and Gallium Donor Ligands: Fused and Spiro‐Type Boracycles
title_full_unstemmed Reactions of a Four‐Membered Borete with Carbon, Silicon, and Gallium Donor Ligands: Fused and Spiro‐Type Boracycles
title_short Reactions of a Four‐Membered Borete with Carbon, Silicon, and Gallium Donor Ligands: Fused and Spiro‐Type Boracycles
title_sort reactions of a four‐membered borete with carbon, silicon, and gallium donor ligands: fused and spiro‐type boracycles
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9322404/
https://www.ncbi.nlm.nih.gov/pubmed/35362629
http://dx.doi.org/10.1002/chem.202200673
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