Title
Remote functionalization : palladium-catalyzed <tex>$C5(sp^{3})-H$</tex> arylation of 1-Boc-3-aminopiperidine through the use of a bidentate directing groupRemote functionalization : palladium-catalyzed <tex>$C5(sp^{3})-H$</tex> arylation of 1-Boc-3-aminopiperidine through the use of a bidentate directing group
Author
Faculty/Department
Faculty of Sciences. Chemistry
Research group
Organic synthesis
Publication type
article
Publication
Subject
Chemistry
Source (journal)
ACS catalysis
Volume/pages
6(2016):7, p. 4486-4490
ISSN
2155-5435
ISI
000379457300052
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
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.
E-info
https://repository.uantwerpen.be/docman/iruaauth/4d76da/133935.pdf
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