Hf(OTf)(4) as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions

Hf(OTf)(4) was identified as a highly potent catalyst (0.1–0.5 mol%) for three-component Mannich reaction under solvent-free conditions. Hf(OTf)(4)-catalyzed Mannich reaction exhibited excellent regioselectivity and diastereoselectivity when alkyl ketones were employed as substrates. (1)H NMR tracin...

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Detalles Bibliográficos
Autores principales: Han, Shuai-Bo, Wei, Jing-Ying, Peng, Xiao-Chong, Liu, Rong, Gong, Shan-Shan, Sun, Qi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7024362/
https://www.ncbi.nlm.nih.gov/pubmed/31963465
http://dx.doi.org/10.3390/molecules25020388
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author Han, Shuai-Bo
Wei, Jing-Ying
Peng, Xiao-Chong
Liu, Rong
Gong, Shan-Shan
Sun, Qi
author_facet Han, Shuai-Bo
Wei, Jing-Ying
Peng, Xiao-Chong
Liu, Rong
Gong, Shan-Shan
Sun, Qi
author_sort Han, Shuai-Bo
collection PubMed
description Hf(OTf)(4) was identified as a highly potent catalyst (0.1–0.5 mol%) for three-component Mannich reaction under solvent-free conditions. Hf(OTf)(4)-catalyzed Mannich reaction exhibited excellent regioselectivity and diastereoselectivity when alkyl ketones were employed as substrates. (1)H NMR tracing of the H/D exchange reaction of ketones in MeOH-d(4) indicated that Hf(OTf)(4) could significantly promote the keto-enol tautomerization, thereby contributing to the acceleration of reaction rate.
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spelling pubmed-70243622020-03-11 Hf(OTf)(4) as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions Han, Shuai-Bo Wei, Jing-Ying Peng, Xiao-Chong Liu, Rong Gong, Shan-Shan Sun, Qi Molecules Article Hf(OTf)(4) was identified as a highly potent catalyst (0.1–0.5 mol%) for three-component Mannich reaction under solvent-free conditions. Hf(OTf)(4)-catalyzed Mannich reaction exhibited excellent regioselectivity and diastereoselectivity when alkyl ketones were employed as substrates. (1)H NMR tracing of the H/D exchange reaction of ketones in MeOH-d(4) indicated that Hf(OTf)(4) could significantly promote the keto-enol tautomerization, thereby contributing to the acceleration of reaction rate. MDPI 2020-01-17 /pmc/articles/PMC7024362/ /pubmed/31963465 http://dx.doi.org/10.3390/molecules25020388 Text en © 2020 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Han, Shuai-Bo
Wei, Jing-Ying
Peng, Xiao-Chong
Liu, Rong
Gong, Shan-Shan
Sun, Qi
Hf(OTf)(4) as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions
title Hf(OTf)(4) as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions
title_full Hf(OTf)(4) as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions
title_fullStr Hf(OTf)(4) as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions
title_full_unstemmed Hf(OTf)(4) as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions
title_short Hf(OTf)(4) as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Solvent-Free Conditions
title_sort hf(otf)(4) as a highly potent catalyst for the synthesis of mannich bases under solvent-free conditions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7024362/
https://www.ncbi.nlm.nih.gov/pubmed/31963465
http://dx.doi.org/10.3390/molecules25020388
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