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α‐Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1‐(Dialkylamino)‐1,2,3‐triazoles

The one‐pot synthesis of a series of sulfonium salts containing transferable diazomethyl groups is described, and the structure of these compounds is elucidated by X‐ray crystallography. Under photochemical conditions, reaction of these salts with N,N‐dialkyl hydrazones affords 1‐(dialkylamino)‐1,2,...

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Detalles Bibliográficos
Autores principales: Li, Xiangdong, Golz, Christopher, Alcarazo, Manuel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8048477/
https://www.ncbi.nlm.nih.gov/pubmed/33351262
http://dx.doi.org/10.1002/anie.202014775
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author Li, Xiangdong
Golz, Christopher
Alcarazo, Manuel
author_facet Li, Xiangdong
Golz, Christopher
Alcarazo, Manuel
author_sort Li, Xiangdong
collection PubMed
description The one‐pot synthesis of a series of sulfonium salts containing transferable diazomethyl groups is described, and the structure of these compounds is elucidated by X‐ray crystallography. Under photochemical conditions, reaction of these salts with N,N‐dialkyl hydrazones affords 1‐(dialkylamino)‐1,2,3‐triazoles via diazomethyl radical addition to the azomethine carbon followed by intramolecular ring closure. The straightforward transformation of the structures thus obtained into mesoionic carbene–metal complexes is also reported and the donor properties of these new ligands characterized.
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spelling pubmed-80484772021-04-16 α‐Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1‐(Dialkylamino)‐1,2,3‐triazoles Li, Xiangdong Golz, Christopher Alcarazo, Manuel Angew Chem Int Ed Engl Communications The one‐pot synthesis of a series of sulfonium salts containing transferable diazomethyl groups is described, and the structure of these compounds is elucidated by X‐ray crystallography. Under photochemical conditions, reaction of these salts with N,N‐dialkyl hydrazones affords 1‐(dialkylamino)‐1,2,3‐triazoles via diazomethyl radical addition to the azomethine carbon followed by intramolecular ring closure. The straightforward transformation of the structures thus obtained into mesoionic carbene–metal complexes is also reported and the donor properties of these new ligands characterized. John Wiley and Sons Inc. 2021-02-17 2021-03-22 /pmc/articles/PMC8048477/ /pubmed/33351262 http://dx.doi.org/10.1002/anie.202014775 Text en © 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Li, Xiangdong
Golz, Christopher
Alcarazo, Manuel
α‐Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1‐(Dialkylamino)‐1,2,3‐triazoles
title α‐Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1‐(Dialkylamino)‐1,2,3‐triazoles
title_full α‐Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1‐(Dialkylamino)‐1,2,3‐triazoles
title_fullStr α‐Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1‐(Dialkylamino)‐1,2,3‐triazoles
title_full_unstemmed α‐Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1‐(Dialkylamino)‐1,2,3‐triazoles
title_short α‐Diazo Sulfonium Triflates: Synthesis, Structure, and Application to the Synthesis of 1‐(Dialkylamino)‐1,2,3‐triazoles
title_sort α‐diazo sulfonium triflates: synthesis, structure, and application to the synthesis of 1‐(dialkylamino)‐1,2,3‐triazoles
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8048477/
https://www.ncbi.nlm.nih.gov/pubmed/33351262
http://dx.doi.org/10.1002/anie.202014775
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