title: Direct, one-pot reductive alkylation of anilines with functionalized acetals mediated by triethylsilane and TFA. Straightforward route for unsymmetrically substituted ethylenediamine.
abstract: A new, robust, and reliable method has been developed for the selective reductive N-alkylation of primary and secondary aromatic amines with some functionalized acetals using TFA/Et(3)SiH as a reagent combination. A variety of unsymmetrically substituted ethylenediamines can be synthesized in a one-pot procedure in excellent yields at room temperature. This new procedure offers significant advantages over previous synthetic approaches, including brevity, mild reaction conditions, excellent yields, and high functional group tolerance.
authors.affiliation: Department of Drug and Health Sciences, University of Urbino Carlo Bo, Piazza del Rinascimento 6, 61029 Urbino (PU), Italy.
authors.forename: Marika
authors.initials: M
authors.lastname: Righi
authors.forename: Annalida
authors.initials: A
authors.lastname: Bedini
authors.forename: Giovanni
authors.initials: G
authors.lastname: Piersanti
authors.forename: Federica
authors.initials: F
authors.lastname: Romagnoli
authors.forename: Gilberto
authors.initials: G
authors.lastname: Spadoni
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000478:Alkylation; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D005029:Ethylenediamines / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012821:Silanes / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D000080:Acetals; D000814:Aniline Compounds; D005029:Ethylenediamines; D012821:Silanes; C512918:triethylsilane; C031234:ethylenediamine; D014269:Trifluoroacetic Acid; C023650:aniline