Vinyl Azides as Radical Acceptors in the Vitamin B(12)-Catalyzed Synthesis of Unsymmetrical Ketones

[Image: see text] Vinyl azides are very reactive species and as such are useful building blocks, in particular, in the synthesis of N-heterocycles. They can also serve as precursors of ketones. These form in reactions of vinyl azides with nucleophiles or radicals. We have found, however, that under...

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Autores principales: Dworakowski, Krzysztof R., Pisarek, Sabina, Hassan, Sidra, Gryko, Dorota
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8650103/
https://www.ncbi.nlm.nih.gov/pubmed/34784475
http://dx.doi.org/10.1021/acs.orglett.1c03321
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author Dworakowski, Krzysztof R.
Pisarek, Sabina
Hassan, Sidra
Gryko, Dorota
author_facet Dworakowski, Krzysztof R.
Pisarek, Sabina
Hassan, Sidra
Gryko, Dorota
author_sort Dworakowski, Krzysztof R.
collection PubMed
description [Image: see text] Vinyl azides are very reactive species and as such are useful building blocks, in particular, in the synthesis of N-heterocycles. They can also serve as precursors of ketones. These form in reactions of vinyl azides with nucleophiles or radicals. We have found, however, that under light irradiation vitamin B(12) catalyzes the reaction of vinyl azides with electrophiles to afford unsymmetrical carbonyl compounds in decent yields. Mechanistic studies revealed that alkyl radicals are key intermediates in this transformation.
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spelling pubmed-86501032021-12-08 Vinyl Azides as Radical Acceptors in the Vitamin B(12)-Catalyzed Synthesis of Unsymmetrical Ketones Dworakowski, Krzysztof R. Pisarek, Sabina Hassan, Sidra Gryko, Dorota Org Lett [Image: see text] Vinyl azides are very reactive species and as such are useful building blocks, in particular, in the synthesis of N-heterocycles. They can also serve as precursors of ketones. These form in reactions of vinyl azides with nucleophiles or radicals. We have found, however, that under light irradiation vitamin B(12) catalyzes the reaction of vinyl azides with electrophiles to afford unsymmetrical carbonyl compounds in decent yields. Mechanistic studies revealed that alkyl radicals are key intermediates in this transformation. American Chemical Society 2021-11-16 2021-12-03 /pmc/articles/PMC8650103/ /pubmed/34784475 http://dx.doi.org/10.1021/acs.orglett.1c03321 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Dworakowski, Krzysztof R.
Pisarek, Sabina
Hassan, Sidra
Gryko, Dorota
Vinyl Azides as Radical Acceptors in the Vitamin B(12)-Catalyzed Synthesis of Unsymmetrical Ketones
title Vinyl Azides as Radical Acceptors in the Vitamin B(12)-Catalyzed Synthesis of Unsymmetrical Ketones
title_full Vinyl Azides as Radical Acceptors in the Vitamin B(12)-Catalyzed Synthesis of Unsymmetrical Ketones
title_fullStr Vinyl Azides as Radical Acceptors in the Vitamin B(12)-Catalyzed Synthesis of Unsymmetrical Ketones
title_full_unstemmed Vinyl Azides as Radical Acceptors in the Vitamin B(12)-Catalyzed Synthesis of Unsymmetrical Ketones
title_short Vinyl Azides as Radical Acceptors in the Vitamin B(12)-Catalyzed Synthesis of Unsymmetrical Ketones
title_sort vinyl azides as radical acceptors in the vitamin b(12)-catalyzed synthesis of unsymmetrical ketones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8650103/
https://www.ncbi.nlm.nih.gov/pubmed/34784475
http://dx.doi.org/10.1021/acs.orglett.1c03321
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