Ben F. Van Steijvoort, N. Kaval, A. A. Kulago
Jun 13, 2016
Citations
0
Influential Citations
36
Citations
Journal
ACS Catalysis
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.