Publication
Title
Remote functionalization : palladium-catalyzed arylation of 1-Boc-3-aminopiperidine through the use of a bidentate directing group
Author
Abstract
A protocol for the Pd-catalyzed C5(sp3)-H arylation of readily available 1-Boc-3-(picolinoylamino)piperidine with iodo(hetero)arenes is reported. The substrate can be obtained from a biorenewable feedstock, namely l-arginine. The use of the right N1 protective group is decisive to get arylation. The addition of a catalytic amount of 2,6-dimethylbenzoic acid and performing the reaction at high concentration are important to achieve a high conversion and yield. The procedure gives arylated 1-Boc-3-(picolinoylamino)piperidines in a regiospecific (C5) and stereospecific (cis) manner. Orthogonal cleavage of the amide over the carbamate group allows one to further selectively derivatize the amino moieties of the piperidine scaffold.
Language
English
Source (journal)
ACS catalysis
Publication
2016
ISSN
2155-5435
Volume/pages
6:7(2016), p. 4486-4490
ISI
000379457300052
Full text (Publishers DOI)
Full text (open access)
The author-created version that incorporates referee comments and is the accepted for publication version Available from 21.06.2017
Full text (publishers version - intranet only)
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 21.06.2016
Last edited 29.03.2017
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