Publication
Title
The role of the alcohol and carboxylic acid in directed ruthenium-catalyzed C(sp3)-H -alkylation of cyclic amines
Author
Abstract
A general directed Ru-catalyzed C(sp3)?H a-alkylation protocol for piperidines (less-reactive substrates than the corresponding five-membered cyclic amines) has been developed. The use of a hindered alcohol (2,4-dimethyl-3-pentanol) as the solvent and catalyst activator, and a catalytic amount of trans-1,2-cyclohexanedicarboxylic acid is necessary to achieve a high conversion to product. This protocol was used to effectively synthesize a number of 2-hexyl- and 2,6-dihexyl piperidines, as well as the alkaloid (+/-)-solenopsin A. Kinetic studies have revealed that the carboxylic acid additive has a significant effect on catalyst initiation, catalyst longevity, and reverses the reaction selectivity compared with the acid-free reaction (promotes alkylation versus competing alkene reduction).
Language
English
Source (journal)
Chemistry: a European journal. - Weinheim
Publication
Weinheim : 2012
ISSN
0947-6539
Volume/pages
18:33(2012), p. 10393-10398
ISI
000307108100031
Full text (Publisher's DOI)
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 13.09.2012
Last edited 09.07.2017
To cite this reference