title: Consecutive three-component synthesis of (hetero)arylated propargyl amides by chemoenzymatic aminolysis-Sonogashira coupling sequence.
abstract: A novel chemoenzymatic three-component synthesis of (hetero)arylated propargyl amides in good yields based upon Novozyme® 435 (Candida antarctica lipase B (CAL-B)) catalyzed aminolysis of methyl carboxylates followed by Sonogashira coupling with (hetero)aryliodides in a consecutive one-pot fashion has been presented. This efficient methodology can be readily concatenated with a CuAAC (Cu catalyzed alkyne azide cycloaddition) as a third consecutive step to furnish 1,4-disubstituted 1,2,3-triazole ligated arylated propargyl amides. This one-pot process can be regarded as a transition metal catalyzed sequence that takes advantage of the copper source still present from the cross-coupling step.
authors.affiliation: Lehrstuhl für Organische Chemie, Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, D-40225, Düsseldorf, Germany. ThomasJJ.Mueller@uni-duesseldorf.de.
authors.forename: Sidra
authors.initials: S
authors.lastname: Hassan
authors.forename: Anja
authors.initials: A
authors.lastname: Ullrich
authors.forename: Thomas J J
authors.initials: TJ
authors.lastname: Müller
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D055162:Biocatalysis; D060326:Chemistry Techniques, Synthetic; D005656:Fungal Proteins / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism*; D010293:Pargyline / Q000737:chemistry
chemical_list: D000577:Amides; D000588:Amines; D005656:Fungal Proteins; D010293:Pargyline; D008049:Lipase; C431349:lipase B, Candida antarctica