Post-Assembly Modification of Peptides by Ligand-Enabled β-C(sp3)-H Arylation of Alanine at the C-Terminus: Overcoming the Inhibition Effect of Peptide Bonds.
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DOI: 10.1021/acs.orglett.1c01481
Abstract: Postassembly modification of peptides via C(sp3)-H functionalization on aliphatic side chains provides a straightforward approach to access functionalized peptides as therapeutics. However, C(sp3)-H functionalization of C-terminal residues remains underdeveloped due to the inhibition effect of… read more here.
Keywords: inhibition effect; ligand enabled; modification peptides; alanine terminus ... See more keywords
Ligand-Enabled Gold-Catalyzed C(sp2)-S Cross-Coupling Reactions.
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DOI: 10.1021/acs.orglett.2c01692
Abstract: Herein we report C(sp2)-S cross-coupling reactions of aryl iodides and arylsulfonyl hydrazides under ligand-enabled, Au(I)/Au(III) redox catalysis. This strategy operates under mild reaction conditions, requires no prefunctionalized aryl coupling partner, and works across several aryl… read more here.
Keywords: ligand enabled; cross coupling; enabled gold; coupling reactions ... See more keywords
Ruthenium-Catalyzed Ligand-Enabled Regiodivergent Difluoroallylation of Aryl C-H Bonds.
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DOI: 10.1021/acs.orglett.3c00873
Abstract: The gem-difluoroallyl group is a sought-after structural motif commonly found in pharmaceutical compounds. Despite its appeal, achieving a controlled synthesis of both α,α- and γ,γ-difluoroallylated compounds has proven to be a challenging task. This study… read more here.
Keywords: catalyzed ligand; ligand enabled; regiodivergent difluoroallylation; ruthenium catalyzed ... See more keywords
Ligand Enabled Pd(II)-Catalyzed γ-C(sp3)-H Lactamization of Native Amides.
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DOI: 10.1021/jacs.1c10183
Abstract: γ-Lactams form important structural cores of a range of medicinally relevant natural products and clinical drugs, principal examples being the new generation of immunomodulatory imide drugs (IMiDs) and the brivaracetam family. Compared to conventional multistep… read more here.
Keywords: sp3 lactamization; enabled catalyzed; ligand enabled; catalyzed sp3 ... See more keywords
One-Step Synthesis of β-Alkylidene-γ-lactones via Ligand-Enabled β,γ-Dehydrogenation of Aliphatic Acids.
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DOI: 10.1021/jacs.2c04779
Abstract: Ligand-enabled Pd-catalyzed regioselective α,β-dehydrogenation of carbonyl compounds via β-methylene C-H activation has recently emerged as a promising transformation. Herein, we report the realization of β,γ-dehydrogenation and subsequent vinyl C-H olefination reactions of free carboxylic acids,… read more here.
Keywords: ligand enabled; one step; alkylidene lactones; aliphatic acids ... See more keywords
Ligand-Enabled β-C(sp3)-H Olefination of Free Carboxylic Acids.
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DOI: 10.1021/jacs.8b06527
Abstract: An acetyl-protected aminoethyl phenyl thioether has been developed to promote C(sp3)-H activation. Significant ligand enhancement is demonstrated by the realization of the first Pd(II)-catalyzed olefination of C(sp3)-H bonds of free carboxylic acids without using an… read more here.
Keywords: sp3 olefination; free carboxylic; enabled sp3; carboxylic acids ... See more keywords
Pd-catalysed ligand-enabled carboxylate-directed highly regioselective arylation of aliphatic acids
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DOI: 10.1038/ncomms14904
Abstract: 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… read more here.
Keywords: arylation aliphatic; aliphatic acids; arylation; ligand enabled ... See more keywords
Ligand-enabled oxidation of gold(i) complexes with o-quinones
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DOI: 10.1039/d2sc03724f
Abstract: Chelating P^P and hemilabile P^N ligands were found to trigger the oxidation of Au(i) complexes by o-benzoquinones. The ensuing Au(iii) catecholate complexes have been characterized by NMR spectroscopy, single crystal X-ray diffraction and X-ray absorption… read more here.
Keywords: ligand enabled; oxidation; spectroscopy; oxidation gold ... See more keywords