Journal ArticleDOI
Regio- and stereoselective synthesis of 2-deoxy-C-aryl glycosides via palladium catalyzed decarboxylative reactions.
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TLDR
An efficient and versatile approach for the synthesis of 2-deoxy-C-aryl glycosides is reported, based on a palladium-catalyzed decarboxylative Heck coupling reaction of benzoic acids and glycals.About:
This article is published in Organic Letters.The article was published on 2011-08-04. It has received 79 citations till now. The article focuses on the topics: Heck reaction & Decarboxylation.read more
Citations
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Journal ArticleDOI
Recent Advances in the Chemical Synthesis of C-Glycosides
TL;DR: Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor.
Journal ArticleDOI
Total Synthesis of Aryl C-Glycoside Natural Products: Strategies and Tactics
TL;DR: The aryl C-glycoside structure is, among the plenty of biologically active natural products, one of the distinct motifs embedded, and the synthetic strategies and tactics employed in the total synthesis of this class of natural products.
Journal ArticleDOI
C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential
Éva Bokor,Sándor Kun,David Goyard,Marietta Tóth,Jean-Pierre Praly,Sébastien Vidal,László Somsák +6 more
TL;DR: This Review summarizes close to 500 primary publications and surveys published since 2000 about the syntheses and diverse bioactivities of C-glycopyranosyl (het)arenes displaying among others antioxidant, antiviral, antibiotic, antiadhesive, cytotoxic, and glycoenzyme inhibitory effects.
Journal ArticleDOI
Recent Advances in Transition Metal-Catalyzed Glycosylation
Matthew J. McKay,Hien M. Nguyen +1 more
TL;DR: Recent advancement is highlighted by examining strategies that employ transition metal catalysis in the synthesis of oligosaccharides and glycoconjugates, which are mild and effective for constructing glycosidic bonds with reduced levels of waste through utilization of sub-stoichiometric amounts of transition metals.
Journal ArticleDOI
Direct C ? H Amidation of Benzoic Acids to Introduce meta- and para-Amino Groups by Tandem Decarboxylation
Donggun Lee,Sukbok Chang +1 more
TL;DR: The Ir-catalyzed mild C-H amidation of benzoic acids with sulfonyl azides was developed to give reactions with high efficiency and functional-group compatibility, and the decarboxylation step was compatible with the amidation conditions, enabling a convenient one-pot, two-step process.
References
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Journal ArticleDOI
Synthesis of Biaryls via Catalytic Decarboxylative Coupling
TL;DR: A safe and convenient cross-coupling strategy for the large-scale synthesis of biaryls, commercially important structures often found in biologically active molecules, using a copper catalyst to generate the carbon nucleophiles in situ via decarboxylation of easily accessible arylcarboxylic acid salts.
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Highly stereoselective approaches to .alpha.- and .beta.-C-glycopyranosides
Journal ArticleDOI
Development of a decarboxylative palladation reaction and its use in a Heck-type olefination of arene carboxylates.
TL;DR: The development of a palladium-catalyzed decarboxylative coupling reaction of arene carboxylates with olefinic substrates is described and reoxidation of the liberated Pd(0) in situ is proposed to establish the catalytic cycle.
Journal ArticleDOI
Biaryl synthesis via Pd-catalyzed decarboxylative coupling of aromatic carboxylates with aryl halides.
Lukas J. Goossen,Nuria Rodríguez,Bettina Melzer,Christophe Linder,Guo-Jun Deng,Laura M. Levy +5 more
TL;DR: A new strategy for the regiospecific construction of unsymmetrical biaryls is presented, in which easily available salts of carboxylic acids are decarboxylated in situ to give arylmetal species that serve as the nucleophilic component in a catalytic cross-coupling reaction with aryal halides.
Journal ArticleDOI
On the Mechanism of the Palladium(II)-Catalyzed Decarboxylative Olefination of Arene Carboxylic Acids. Crystallographic Characterization of Non-Phosphine Palladium(II) Intermediates and Observation of Their Stepwise Transformation in Heck-like Processes
TL;DR: There are notable differences in reactivity between arylpalladium(II) intermediates generated by decarboxylative palladation and those produced in conventional Heck reactions, and it is found that more electron-rich alkenes react preferentially with an aryl group and trifluoroacetate intermediate formed by decarate palladium-based reactions, whereas an opposite trend is found inventional Heck reactions.
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