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Molecules 2017, 22(1), 146; doi:10.3390/molecules22010146

Mechanochemical Lignin-Mediated Strecker Reaction

1
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany
2
Angewandte Organische Chemie, Hochschule Niederrhein, University of Applied Sciences, Adlerstr. 32, D-47798 Krefeld, Germany
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 26 November 2016 / Revised: 7 January 2017 / Accepted: 10 January 2017 / Published: 17 January 2017
(This article belongs to the Special Issue Mechanochemistry)
View Full-Text   |   Download PDF [2940 KB, uploaded 17 January 2017]   |  

Abstract

A mechanochemical Strecker reaction involving a wide range of aldehydes (aromatic, heteroaromatic and aliphatic), amines, and KCN afforded a library of α-aminonitriles upon mechanical activation. This multicomponent process was efficiently activated by lignocellulosic biomass as additives. Particularly, commercially available Kraft lignin was found to be the best activator for the addition of cyanide to the in situ formed imines. A comparative study of the 31P-NMR (Nuclear Magnetic Resonance) along with IR (Infrared) data analysis for the Kraft lignin and methylated Kraft lignin samples ascertained the importance of the free hydroxyl groups in the activation of the mechanochemical reaction. The solvent-free mechanochemical Strecker reaction was then coupled with a lactamization process leading to the formation of the N-benzylphthalimide (5a) and the isoindolinone derivative 6a. View Full-Text
Keywords: mechanochemistry; lignin; Strecker reaction; multicomponent reactions; ball milling mechanochemistry; lignin; Strecker reaction; multicomponent reactions; ball milling
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Dabral, S.; Turberg, M.; Wanninger, A.; Bolm, C.; Hernández, J.G. Mechanochemical Lignin-Mediated Strecker Reaction. Molecules 2017, 22, 146.

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