3.7. Palladium Nanoparticles as Catalysts 888 3.8. Other Transition-Metal Complexes 888 3.9. Transition-Metal-Free Reactions 889 4. Applications 889 4.1. Alkynylation of Arenes 889 4.2. Alkynylation of Heterocycles 891 4.3. Synthesis of Enynes and Enediynes 894 4.4. Synthesis of Ynones 896 4.5. Synthesis of Carbocyclic Systems 897 4.6. Synthesis of Heterocyclic Systems 898 4.7. Synthesis of Natural Products 903 4.8. Synthesis of Electronic and Electrooptical Molecules 906

https://www.chem.ccu.edu.tw/~joyce/referance/ericyang/Chem.%20Rev/Chem.%20Rev.%202007,%20107,%20874-922.pdf

The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry†

The cores of many types of polymers, ligands, natural products, and pharmaceuticals contain biaryl or substituted aromatic structures, and efficient methods of synthesizing these structures are crucial to the work of a broad spectrum of organic chemists. Recently, Pd-catalyzed carbon−carbon bond-forming processes, particularly the Suzuki−Miyaura cross-coupling reaction (SMC), have risen in popularity for this purpose. The SMC has many advantages over other methods for constructing these moieties, including mild conditions, high tolerance toward functional groups, the commercial availability and stability of its reagents, and the ease of handling and separating byproducts from its reaction mixtures. Until 1998, most catalysts for the SMC employed triarylphosphine ligands. More recently, new bulky and electron-rich phosphine ligands, which can dramatically improve the efficiency and selectivity of such cross-coupling reactions, have been introduced. In the course of our studies on carbon−nitrogen bond-formi...

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Palladium-Catalyzed Suzuki-Miyaura Cross-coupling Reactions Employing Dialkylbiaryl Phosphine Ligands

4.4. Pd on Modified Silica 159 4.5. Pd on Clay and Other Inorganic Materials 159 5. Stille, Fukuyama, and Negishi Reactions 159 5.1. Stille Reactions 159 5.1.1. Pd on Carbon (Pd/C) 159 5.1.2. Palladium on KF/Al2O3 159 5.1.3. Pd on Modified Silica (SiO2/TEG/Pd) 159 5.2. Fukuyama Reactions 159 5.2.1. Pd on Carbon (Pd/C) 159 5.2.2. Pd(OH)2 on Carbon (Perlman’s Catalyst) 160 5.3. Pd/C-Catalyzed Negishi Reactions 160 6. Ullmann-Type Coupling Reactions 161 6.1. Pd/C-Catalyzed Aryl−Aryl Coupling 161 6.2. Pd/C-Catalyzed Homocoupling of Vinyl Halides 162

https://www.chem.ccu.edu.tw/~joyce/referance/ericyang/Chem.%20Rev/Chem.%20Rev.%202007,%20107,%20133-173.pdf

Carbon-Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts

Selected patented cross-coupling reaction technologies.

Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.

Boronic acids are valued by organic chemists for their important role in the synthesis of biphenyls via a palladium(0) catalysed cross-coupling reaction with aryl halides (Suzuki reaction). Despite their synthetic utilityand known biological activities heterocyclic boronic acids feature less frequently often due to difficulties in their synthesis. This paper provides an overview of the synthesis and applications of a range of heterocyclic boronic acids.

The Synthesis and Applications of Heterocyclic Boronic Acids

SCOPE: Resveratrol is a plant-derived polyphenol with chemotherapeutic properties in animal cancer models and many biochemical effects in vitro Its bioavailability is low and raises the possibility that the metabolites of resveratrol have biological effects Here we investigate the actions of resveratrol 3-O-d-glucuronide, resveratrol 4'-O-d-glucuronide, and resveratrol 3-O-d-sulfate on the growth of colon cancer cells in vitro METHODS AND RESULTS: The growth of Caco-2, HCT-116, and CCL-228 cells was measured using the neutral red and MTT assays Resveratrol and each metabolite inhibited cell growth with IC50 values of 98-31 μM Resveratrol caused S phase arrest in all three cell lines Resveratrol 3-O-d-glucuronide and resveratrol 4'-O-d-glucuronide caused G1 arrest in CCL-228 and Caco-2 cells Resveratrol 3-O-d-sulfate had no effect on cell cycle Growth inhibition was reversed by an inhibitor of AMP-activated protein kinase (compound C) or an adenosine A3 receptor antagonist (MRS1191) The A3 receptor agonist 2Cl-IB-MECA inhibited growth and A3 receptors were detected in all cell lines The resveratrol glucuronides also reduced cyclin D1 levels but at higher concentrations than in growth experiments and generally did not increase phosphorylated AMP-activated protein kinase CONCLUSION: Resveratrol glucuronides inhibit cell growth by G1 arrest and cyclin D1 depletion, and our results strongly suggest a role for A3 adenosine receptors in this inhibition

Resveratrol 3-O-d-glucuronide and resveratrol 4'-O-d-glucuronide inhibit colon cancer cell growth: Evidence for a role of A3 adenosine receptors, cyclin D1 depletion, and G1 cell cycle arrest

3-Aminopropyl functionalised silica gel may be readily transformed into a stable immobilised palladium catalyst. This catalyst was then successfully employed in a series of fast, copper-free Sonogashira coupling reactions.

Elizabeth Tyrrell

Papers

The Synthesis and Applications of Heterocyclic Boronic Acids

Resveratrol 3-O-d-glucuronide and resveratrol 4'-O-d-glucuronide inhibit colon cancer cell growth: Evidence for a role of A3 adenosine receptors, cyclin D1 depletion, and G1 cell cycle arrest

A Novel Silica-Supported Palladium Catalyst for a Copper-Free Sonogashira Coupling Reaction

The application of 1H nuclear magnetic resonance spectroscopy for the determination of the absolute configuration of chiral carboxylic acids

The synthesis and characterisation of immobilised palladium carbene complexes and their application to heterogeneous catalysis