The impact of the development of sulfur therapeutics is instrumental to the evolution of the pharmaceutical industry. Sulfur-derived functional groups can be found in a broad range of pharmaceuticals and natural products. For centuries, sulfur continues to maintain its status as the dominating heteroatom integrated into a set of 362 sulfur-containing FDA approved drugs (besides oxygen or nitrogen) through the present. Sulfonamides, thioethers, sulfones and Penicillin are the most common scaffolds in sulfur containing drugs, which are well studied both on synthesis and application during the past decades. In this review, these four moieties in pharmaceuticals and recent advances in the synthesis of the corresponding core scaffolds are presented.

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Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

The introduction of sulfur atoms onto target molecules is an important area in organic synthesis, in particular in the synthesis of pharmaceutical compounds, and a wide variety of sulfuration agents have been developed for thionation reactions over the past few decades. In this Focus Review, we collect and summarize the C-S bond-formation reactions that have been used to construct C-S bonds in natural products and pharmaceutical compounds.

Transfer of sulfur: from simple to diverse.

The high utility of halogenated organic compounds has prompted the development of a vast number of transformations which install the carbon–halogen motif. Traditional routes to these building blocks have commonly involved multiple steps, harsh reaction conditions, and the use of stoichiometric and/or toxic reagents. In this regard, using transition metals to catalyze the synthesis of organohalides has become a mature field in itself, and applying these technologies has allowed for a decrease in the production of waste, higher levels of regio- and stereoselectivity, and the ability to produce enantioenriched target compounds. Furthermore, transition metals offer the distinct advantage of possessing a diverse spectrum of mechanistic possibilities which translate to the capability to apply new substrate classes and afford novel and difficult-to-access structures. This Review provides comprehensive coverage of modern transition metal-catalyzed syntheses of organohalides via a diverse array of mechanisms. Atte...

Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

Sulfur-containing molecules such as thioethers are commonly found in chemical biology, organic synthesis, and materials chemistry. While many reliable methods have been developed for preparing these compounds, harsh reaction conditions are usually required in the traditional methods. The transition metals have been applied in this field, and the palladium-catalyzed coupling of thiols with aryl halides and pseudo halides is one of the most important methods in the synthesis of thioethers. Other metals have also been used for the same purpose. Here, we summarize recent efforts in metal-catalyzed C-S bond cross-coupling reactions, focusing especially on the coupling of thiols with aryl- and vinyl halides based on different metals.

Transition-metal-catalyzed C-S bond coupling reaction.

https://pubs.rsc.org/en/content/articlepdf/2019/cc/c9cc01047e

Recent advances of 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) in photocatalytic transformations.

Efficient access to 1,4-benzothiazine: palladium-catalyzed double C-S bond formation using Na2S2O3 as sulfurating reagent.

Direct cross-coupling access to diverse aromatic sulfide: palladium-catalyzed double C-S bond construction using Na2S2O3 as a sulfurating reagent.

Sulfur–carbon bond construction has gained great attention recently since sulfur-containing organic molecules serve important functions in the pharmaceutical industry, agrochemistry, food chemistry, and materials science. Diverse sulfur sources have been developed over the past few decades, in which thiosulfates showed unique properties in many transformations. In this Perspective, we summarized recent research on sulfur–carbon bond formation involving thiosulfates.

Zongjun Qiao

Papers

Efficient access to 1,4-benzothiazine: palladium-catalyzed double C-S bond formation using Na2S2O3 as sulfurating reagent.

Direct cross-coupling access to diverse aromatic sulfide: palladium-catalyzed double C-S bond construction using Na2S2O3 as a sulfurating reagent.

Recent developments in sulfur-carbon bond formation reaction involving thiosulfates.

Ligand-Controlled Divergent Cross-Coupling Involving Organosilicon Compounds for Thioether and Thioester Synthesis.

CO2-promoted oxidative cross-coupling reaction for C–S bond formation via masked strategy in an odourless way