title: Mechanochemical Lignin-Mediated Strecker Reaction.
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 the31P-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 theN-benzylphthalimide (5a) and the isoindolinone derivative6a.
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany. saumya.dabral@oc.rwth-aachen.de.
authors.forename: Saumya
authors.initials: S
authors.lastname: Dabral
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany. mathias.turberg@rwth-aachen.de.
authors.forename: Mathias
authors.initials: M
authors.lastname: Turberg
authors.affiliation: Angewandte Organische Chemie, Hochschule Niederrhein, University of Applied Sciences, Adlerstr. 32, D-47798 Krefeld, Germany. andrea.wanninger@hs-niederrhein.de.
authors.forename: Andrea
authors.initials: A
authors.lastname: Wanninger
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany. carsten.bolm@oc.rwth-aachen.de.
authors.forename: Carsten
authors.initials: C
authors.lastname: Bolm
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany. jose.hernandez@oc.rwth-aachen.de.
authors.forename: José G
authors.initials: JG
authors.lastname: Hernández
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D018533:Biomass; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D003486:Cyanides / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D008031:Lignin / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D000447:Aldehydes; D000588:Amines; D003486:Cyanides; D007097:Imines; C076151:Kraft lignin; D008031:Lignin
keywords: Strecker reaction; ball milling; lignin; mechanochemistry; multicomponent reactions