Title
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Remote functionalization : palladium-catalyzed arylation of 1-Boc-3-aminopiperidine through the use of a bidentate directing group
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Author
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Abstract
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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. |
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Language
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English
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Source (journal)
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ACS catalysis. - -
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Publication
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2016
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ISSN
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2155-5435
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DOI
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10.1021/ACSCATAL.6B00841
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Volume/pages
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6
:7
(2016)
, p. 4486-4490
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ISI
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000379457300052
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Full text (Publisher's DOI)
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Full text (open access)
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Full text (publisher's version - intranet only)
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