Hf(OTf)(4)-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones

Hafnium(IV) triflate (Hf(OTf)(4)) has been identified as a potent catalyst for the direct three-component synthesis of β-carbamate ketones. This new method, featuring a low catalyst loading, fast reaction rate, and solvent-free conditions, provided facile access to a diversity of carbamate-protected...

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Autores principales: Chen, Zhen-Zhen, Yang, Dong-Zhao, Dong, Ying-Ying, Chi, Mei, Pu, Shou-Zhi, Sun, Qi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8840004/
https://www.ncbi.nlm.nih.gov/pubmed/35164390
http://dx.doi.org/10.3390/molecules27031122
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author Chen, Zhen-Zhen
Yang, Dong-Zhao
Dong, Ying-Ying
Chi, Mei
Pu, Shou-Zhi
Sun, Qi
author_facet Chen, Zhen-Zhen
Yang, Dong-Zhao
Dong, Ying-Ying
Chi, Mei
Pu, Shou-Zhi
Sun, Qi
author_sort Chen, Zhen-Zhen
collection PubMed
description Hafnium(IV) triflate (Hf(OTf)(4)) has been identified as a potent catalyst for the direct three-component synthesis of β-carbamate ketones. This new method, featuring a low catalyst loading, fast reaction rate, and solvent-free conditions, provided facile access to a diversity of carbamate-protected Mannich bases. A mechanistic investigation indicated that the three-component reaction proceeds via sequential aldol condensation and aza-Michael addition, but not the Mannich-type pathway.
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spelling pubmed-88400042022-02-13 Hf(OTf)(4)-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones Chen, Zhen-Zhen Yang, Dong-Zhao Dong, Ying-Ying Chi, Mei Pu, Shou-Zhi Sun, Qi Molecules Article Hafnium(IV) triflate (Hf(OTf)(4)) has been identified as a potent catalyst for the direct three-component synthesis of β-carbamate ketones. This new method, featuring a low catalyst loading, fast reaction rate, and solvent-free conditions, provided facile access to a diversity of carbamate-protected Mannich bases. A mechanistic investigation indicated that the three-component reaction proceeds via sequential aldol condensation and aza-Michael addition, but not the Mannich-type pathway. MDPI 2022-02-08 /pmc/articles/PMC8840004/ /pubmed/35164390 http://dx.doi.org/10.3390/molecules27031122 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Chen, Zhen-Zhen
Yang, Dong-Zhao
Dong, Ying-Ying
Chi, Mei
Pu, Shou-Zhi
Sun, Qi
Hf(OTf)(4)-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones
title Hf(OTf)(4)-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones
title_full Hf(OTf)(4)-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones
title_fullStr Hf(OTf)(4)-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones
title_full_unstemmed Hf(OTf)(4)-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones
title_short Hf(OTf)(4)-Catalyzed Three-Component Synthesis of N-Carbamate-Protected β-Amino Ketones
title_sort hf(otf)(4)-catalyzed three-component synthesis of n-carbamate-protected β-amino ketones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8840004/
https://www.ncbi.nlm.nih.gov/pubmed/35164390
http://dx.doi.org/10.3390/molecules27031122
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