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JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
Pd-catalysed ligand-enabled carboxylate-directed highly regioselective arylation of aliphatic acids.
Nature Communications 2017 April 7
α-amino acids bearing aromatic side chains are important synthetic units in the synthesis of peptides and natural products. Although various β-C-H arylation methodologies for amino acid derivatives involving the assistance of directing groups have been extensively developed, syntheses that directly employ N-protected amino acids as starting materials remain rare. Herein, we report an N-acetylglycine-enabled Pd-catalysed carboxylate-directed β-C(sp3 )-H arylation of aliphatic acids. In this way, various non-natural amino acids can be directly prepared from phthaloylalanine in one step in good to excellent yields. Furthermore, a series of aliphatic acids have been shown to be amenable to this transformation, affording β-arylated propionic acid derivatives in moderate to good yields. More importantly, this ligand-enabled direct β-C(sp3 )-H arylation could be easily scaled-up to 10 g under reflux conditions, highlighting the potential utility of this synthetic method.
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