New Organocatalyst Scaffolds with High Activity in Promoting Hydrazone and Oxime Formation at Neutral pH

[Image: see text] The discovery of two new classes of catalysts for hydrazone and oxime formation in water at neutral pH, namely 2-aminophenols and 2-(aminomethyl)benzimidazoles, is reported. Kinetics studies in aqueous solutions at pH 7.4 revealed rate enhancements up to 7-fold greater than with cl...

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Autores principales: Larsen, Dennis, Pittelkow, Michael, Karmakar, Saswata, Kool, Eric T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4301078/
https://www.ncbi.nlm.nih.gov/pubmed/25545888
http://dx.doi.org/10.1021/ol503372j
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author Larsen, Dennis
Pittelkow, Michael
Karmakar, Saswata
Kool, Eric T.
author_facet Larsen, Dennis
Pittelkow, Michael
Karmakar, Saswata
Kool, Eric T.
author_sort Larsen, Dennis
collection PubMed
description [Image: see text] The discovery of two new classes of catalysts for hydrazone and oxime formation in water at neutral pH, namely 2-aminophenols and 2-(aminomethyl)benzimidazoles, is reported. Kinetics studies in aqueous solutions at pH 7.4 revealed rate enhancements up to 7-fold greater than with classic aniline catalysis. 2-(Aminomethyl)benzimidazoles were found to be effective catalysts with otherwise challenging aryl ketone substrates.
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spelling pubmed-43010782015-12-29 New Organocatalyst Scaffolds with High Activity in Promoting Hydrazone and Oxime Formation at Neutral pH Larsen, Dennis Pittelkow, Michael Karmakar, Saswata Kool, Eric T. Org Lett [Image: see text] The discovery of two new classes of catalysts for hydrazone and oxime formation in water at neutral pH, namely 2-aminophenols and 2-(aminomethyl)benzimidazoles, is reported. Kinetics studies in aqueous solutions at pH 7.4 revealed rate enhancements up to 7-fold greater than with classic aniline catalysis. 2-(Aminomethyl)benzimidazoles were found to be effective catalysts with otherwise challenging aryl ketone substrates. American Chemical Society 2014-12-29 2015-01-16 /pmc/articles/PMC4301078/ /pubmed/25545888 http://dx.doi.org/10.1021/ol503372j Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Larsen, Dennis
Pittelkow, Michael
Karmakar, Saswata
Kool, Eric T.
New Organocatalyst Scaffolds with High Activity in Promoting Hydrazone and Oxime Formation at Neutral pH
title New Organocatalyst Scaffolds with High Activity in Promoting Hydrazone and Oxime Formation at Neutral pH
title_full New Organocatalyst Scaffolds with High Activity in Promoting Hydrazone and Oxime Formation at Neutral pH
title_fullStr New Organocatalyst Scaffolds with High Activity in Promoting Hydrazone and Oxime Formation at Neutral pH
title_full_unstemmed New Organocatalyst Scaffolds with High Activity in Promoting Hydrazone and Oxime Formation at Neutral pH
title_short New Organocatalyst Scaffolds with High Activity in Promoting Hydrazone and Oxime Formation at Neutral pH
title_sort new organocatalyst scaffolds with high activity in promoting hydrazone and oxime formation at neutral ph
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4301078/
https://www.ncbi.nlm.nih.gov/pubmed/25545888
http://dx.doi.org/10.1021/ol503372j
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AT karmakarsaswata neworganocatalystscaffoldswithhighactivityinpromotinghydrazoneandoximeformationatneutralph
AT koolerict neworganocatalystscaffoldswithhighactivityinpromotinghydrazoneandoximeformationatneutralph

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