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Molecules 2015, 20(3), 4136-4147; doi:10.3390/molecules20034136

DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems

1
Institute of Organic Chemistry, University of Regensburg, Universitätsstr. 31, Regensburg 93053, Germany
2
Institute Charles Gerhardt Montpellier-UMR 5253 CNRS-UMII-ENSCM-UMI, Matériaux Avancés pour la Catalyse et la Santé, 8 rue de l'École Normale, 34296 Montpellier Cedex 5, France
3
IQAC-CSIC, Jordi Girona 18–26, Barcelona 08034, Spain
*
Author to whom correspondence should be addressed.
Academic Editor: Raquel P. Herrera
Received: 5 February 2015 / Revised: 18 February 2015 / Accepted: 27 February 2015 / Published: 4 March 2015
(This article belongs to the Collection Recent Advances in Organocatalysis)
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Abstract

In this manuscript we report a critical evaluation of the ability of natural DNA to mediate the nitroaldol (Henry) reaction at physiological temperature in pure water. Under these conditions, no background reaction took place (i.e., control experiment without DNA). Both heteroaromatic aldehydes (e.g., 2-pyridinecarboxaldehyde) and aromatic aldehydes bearing strong or moderate electron-withdrawing groups reacted satisfactorily with nitromethane obeying first order kinetics and affording the corresponding β-nitroalcohols in good yields within 24 h. In contrast, aliphatic aldehydes and aromatic aldehydes having electron-donating groups either did not react or were poorly converted. Moreover, we discovered that a number of metal-free organic buffers efficiently promote the Henry reaction when they were used as reaction media without adding external catalysts. This constitutes an important observation because the influence of organic buffers in chemical processes has been traditionally underestimated. View Full-Text
Keywords: DNA; C–C bond formation; nitroaldol reaction; Henry reaction; buffer solutions DNA; C–C bond formation; nitroaldol reaction; Henry reaction; buffer solutions
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Häring, M.; Pérez-Madrigal, M.M.; Kühbeck, D.; Pettignano, A.; Quignard, F.; Díaz, D.D. DNA-Catalyzed Henry Reaction in Pure Water and the Striking Influence of Organic Buffer Systems. Molecules 2015, 20, 4136-4147.

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