Cyano(triphenylsilyl)phosphanide as a Building Block for P,C,N Conjugated Molecules

The cyano(triphenylsilyl)phosphanide anion was prepared as a sodium salt from 2‐phosphaethynolate. The electronic structure of this new cyano(silyl)phosphanide was studied via computational methods and its reactivity investigated using various electrophiles and Lewis acids, demonstrating its P‐ and...

Descripción completa

Detalles Bibliográficos
Autores principales: Le Corre, Grégoire, Gamboa‐Carballo, Juan José, Li, Zhongshu, Grützmacher, Hansjörg
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9297940/
https://www.ncbi.nlm.nih.gov/pubmed/34463413
http://dx.doi.org/10.1002/anie.202108295
_version_ 1784750586863812608
author Le Corre, Grégoire
Gamboa‐Carballo, Juan José
Li, Zhongshu
Grützmacher, Hansjörg
author_facet Le Corre, Grégoire
Gamboa‐Carballo, Juan José
Li, Zhongshu
Grützmacher, Hansjörg
author_sort Le Corre, Grégoire
collection PubMed
description The cyano(triphenylsilyl)phosphanide anion was prepared as a sodium salt from 2‐phosphaethynolate. The electronic structure of this new cyano(silyl)phosphanide was studied via computational methods and its reactivity investigated using various electrophiles and Lewis acids, demonstrating its P‐ and N‐nucleophilicity. The ambident reactivity is in agreement with computations. The silyl group also shows lability and therefore the cyano(silyl)phosphanide can be considered as a phosphacyanamide synthon, [PCN](2−), and serves as building block for the transfer of a PCN moiety.
format Online
Article
Text
id pubmed-9297940
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-92979402022-07-21 Cyano(triphenylsilyl)phosphanide as a Building Block for P,C,N Conjugated Molecules Le Corre, Grégoire Gamboa‐Carballo, Juan José Li, Zhongshu Grützmacher, Hansjörg Angew Chem Int Ed Engl Communications The cyano(triphenylsilyl)phosphanide anion was prepared as a sodium salt from 2‐phosphaethynolate. The electronic structure of this new cyano(silyl)phosphanide was studied via computational methods and its reactivity investigated using various electrophiles and Lewis acids, demonstrating its P‐ and N‐nucleophilicity. The ambident reactivity is in agreement with computations. The silyl group also shows lability and therefore the cyano(silyl)phosphanide can be considered as a phosphacyanamide synthon, [PCN](2−), and serves as building block for the transfer of a PCN moiety. John Wiley and Sons Inc. 2021-10-20 2021-11-15 /pmc/articles/PMC9297940/ /pubmed/34463413 http://dx.doi.org/10.1002/anie.202108295 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Le Corre, Grégoire
Gamboa‐Carballo, Juan José
Li, Zhongshu
Grützmacher, Hansjörg
Cyano(triphenylsilyl)phosphanide as a Building Block for P,C,N Conjugated Molecules
title Cyano(triphenylsilyl)phosphanide as a Building Block for P,C,N Conjugated Molecules
title_full Cyano(triphenylsilyl)phosphanide as a Building Block for P,C,N Conjugated Molecules
title_fullStr Cyano(triphenylsilyl)phosphanide as a Building Block for P,C,N Conjugated Molecules
title_full_unstemmed Cyano(triphenylsilyl)phosphanide as a Building Block for P,C,N Conjugated Molecules
title_short Cyano(triphenylsilyl)phosphanide as a Building Block for P,C,N Conjugated Molecules
title_sort cyano(triphenylsilyl)phosphanide as a building block for p,c,n conjugated molecules
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9297940/
https://www.ncbi.nlm.nih.gov/pubmed/34463413
http://dx.doi.org/10.1002/anie.202108295
work_keys_str_mv AT lecorregregoire cyanotriphenylsilylphosphanideasabuildingblockforpcnconjugatedmolecules
AT gamboacarballojuanjose cyanotriphenylsilylphosphanideasabuildingblockforpcnconjugatedmolecules
AT lizhongshu cyanotriphenylsilylphosphanideasabuildingblockforpcnconjugatedmolecules
AT grutzmacherhansjorg cyanotriphenylsilylphosphanideasabuildingblockforpcnconjugatedmolecules

Ejemplares similares