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†

Introduction Cationic domino reactions Anionic domino reactions Radical domino reactions Pericyclic domino reactions Photochemically induced domino processes Transition metal catalysis Domino reactions initiated by oxidation or reduction Enzymes in domino reactions Multicomponent reactions Special techniques in domino reactions

Domino Reactions in Organic Synthesis

The coupling of aryl or vinyl halides with terminal acetylenes catalysed by palladium and other transition metals, commonly termed as Sonogashira cross-coupling reaction, is one of the most important and widely used sp2–sp carbon–carbon bond formation reactions in organic synthesis, frequently employed in the synthesis of natural products, biologically active molecules, heterocycles, molecular electronics, dendrimers and conjugated polymers or nanostructures. This critical review focuses on developments in the Sonogashira reaction achieved in recent years concerning catalysts, reaction conditions and substrates (352 references).

Recent advances in Sonogashira reactions

Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.

New principles for glycoside-bond formation.

Stereochemical Control in Organic-Synthesis Using Silicon-Containing Compounds

Chemoselectivity in the radical cyclization of tethered α-D-erythro-oct-2,6-dienopyranosides can be accomplished by changes in the nature of the tether and/or in the oxidation state at the termini of the olefins, to afford stereoselectively 3-deoxy-3-C-substituted carbohydrates, off-template branched-chain sugars, or functionalized cyclopentanes.

Fine tuning of chemo- and stereo-selectivity in cyclization reactions of tethered radicals derived from 4-O-substituted-α-D-erythro-oct-2,6-dienopyranosides. Stereoselective access to carbocycles and branched-chain sugars

Herein we describe the synthesis, and computationally aided photophysical characterization of a new set of urea-bridged bis-BODIPY derivatives. These new dyads are efficiently obtained by a one-pot tandem Staudinger/aza-Wittig ureation protocol, from easily accessible meso-phenyl ortho-azidomethyl BODIPYs. These symmetric bis-BODIPYs outstand by a high absorption probability and excellent fluorescence and laser emission in less polar media. Nevertheless, this emission ability decreases in more polar media, which is ascribed to a light-induced charge-transfer from the urea spacer to the dipyrrin core, a process that can be modulated by appropriate changes in the substitution pattern of the BODIPY core. Furthermore, this ureation protocol can also be employed for the direct conjugation of our BODIPY-azides to amine-containing compounds, thus providing access to fluorescent non-symmetric ureas.

Solvent-Sensitive Emitting Urea-Bridged bis-BODIPYs: Ready Access by a One-Pot Tandem Staudinger/Aza-Wittig Ureation

A route to functionalized branched-chain amino sugars via nitrous acid promoted spiroaziridine formation

The presence of an unsaturation in a pyranose derivative provides a powerful handle for the creation of new compounds displaying a variety of molecular skeletons. This contribution focuses on investigations related to the use of pyranose glycals in the creation of skeletally-diverse derivatives that have appeared in the literature during the last eight years.

J. Cristobal Lopez

Papers

Fine tuning of chemo- and stereo-selectivity in cyclization reactions of tethered radicals derived from 4-O-substituted-α-D-erythro-oct-2,6-dienopyranosides. Stereoselective access to carbocycles and branched-chain sugars

Solvent-Sensitive Emitting Urea-Bridged bis-BODIPYs: Ready Access by a One-Pot Tandem Staudinger/Aza-Wittig Ureation

A route to functionalized branched-chain amino sugars via nitrous acid promoted spiroaziridine formation

Pyranose glycals in the generation of skeletal diversity

Stereocontrolled entry to 2,5-disubstituted tetrahydrofurans from hex-2-enono-δ-lactones under mild conditions