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N-Heterocyclic carbene (NHC) organocatalysis using aliphatic aldehydes

Barik, S and Biju, AT (2020) N-Heterocyclic carbene (NHC) organocatalysis using aliphatic aldehydes. In: Chemical Communications, 56 (99). pp. 15484-15495.

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Official URL: https://dx.doi.org/10.1109/10.1039/d0cc06867e


Catalysis using N-heterocyclic carbenes (NHCs) has been widely employed for the umpolung of aldehydes, and these reactions proceed via the generation of nucleophilic Breslow intermediates. These acyl anion equivalents can be added to aldehydes, ketones, imines, Michael acceptors, and even unactivated carbon-carbon multiple bonds. In a majority of the cases, aromatic aldehydes are used in NHC catalysis. However, the use of aliphatic aldehydes is relatively less explored because of the low electrophilicity of the aliphatic aldehydes compared to aromatic aldehydes for the nucleophilic addition of carbenes, and the presence of α-acidic protons leading to side reactions under basic conditions. There are several NHC-catalyzed reactions that engage aliphatic aldehydes, and this Highlight summarizes the advances in NHC catalysis using aliphatic aldehydes as substrates. This journal is © 2020 The Royal Society of Chemistry.

Item Type: Journal Article
Publication: Chemical Communications
Publisher: Royal Society of Chemistry
Additional Information: Copyright to this article belongs to Royal Society of Chemistry
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 28 Jan 2021 05:28
Last Modified: 28 Jan 2021 05:28
URI: http://eprints.iisc.ac.in/id/eprint/67601

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