title: Decarboxylative Reissert type trifluoro- and trichloro-methylation of (iso)quinoline derivatives in batch and continuous flow.
abstract: Two decarboxylative methods providing access to N-alkylated α-trihalomethylated heterocyclic amines have been developed. A batch protocol in which methyl trifluoroacetate acts both as a methylating reagent and subsequently as a nucleophilic trifluoromethyl anion precursor upon its addition to (iso)quinoline derivatives. Next, a telescoped continuous flow process, forming the corresponding α-trichloromethylated heterocyclic amines, utilizing a similar decarboxylation of trichloroacetic acid, was developed and taken to scale-up.
authors.affiliation: Department of Engineering, Interdisciplinary Nanoscience Center (iNANO), Aarhus University, Finladsgade 22, 8200 Aarhus N, Denmark. lindhardt@eng.au.dk.
authors.forename: M
authors.initials: M
authors.lastname: Therkelsen
authors.forename: M T
authors.initials: MT
authors.lastname: Rasmussen
authors.forename: A T
authors.initials: AT
authors.lastname: Lindhardt
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003653:Decarboxylation; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D000588:Amines; D006571:Heterocyclic Compounds; D011804:Quinolines; D014269:Trifluoroacetic Acid