Publication
Title
The use of calcium carbide as acetylene source in a three-component coupling with omega-chlorinated ketones and primary amines
Author
Abstract
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.
Language
English
Source (journal)
Chemistry: a European journal. - Weinheim
Publication
Weinheim : 2018
ISSN
0947-6539
Volume/pages
24 :62 (2018) , p. 16645-16651
ISI
000449551100024
Pubmed ID
30112778
Full text (Publisher's DOI)
Full text (open access)
Full text (publisher's version - intranet only)
UAntwerpen
Faculty/Department
Research group
Project info
Catalytic alkynylation and alkenylation of functionalized imines and further transformation of the obtained propargylic and allylic amines
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 10.12.2018
Last edited 20.09.2021
To cite this reference