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The use of calcium carbide as acetylene source in a three-component coupling with omega-chlorinated ketones and primary amines

Tijdschriftbijdrage - Tijdschriftartikel

Calcium carbide was used in a Cu-I-catalysed three-component coupling with omega-chlorinated ketones and primary amines to generate terminal 2-alkynyl-N-heterocycles. The formation of an imine and the subsequent intramolecular substitution results in an active electrophilic iminium species, which can be alkynylated by in situ formed copper acetylide. A number of aliphatic primary (functionalised) amines and aliphatic or aromatic alkynes together with different alkyl- or aryl-substituted gamma- or delta-chloroketones could be used. Simple acid-base workup instead of column chromatography can be applied to obtain the resulting 2-alkynylpyrrolidines and 2-alkynylpiperidines.
Tijdschrift: Chemistry: a European journal
ISSN: 0947-6539
Volume: 24
Pagina's: 16645 - 16651
Jaar van publicatie:2018
Trefwoorden:A1 Journal article
BOF-keylabel:ja
BOF-publication weight:2
CSS-citation score:2
Authors from:Higher Education
Toegankelijkheid:Open