The development of mild and general methods for C–S bond formation has received significant attention because the C–S bond is indispensable in many important biological and pharmaceutical compounds. Early examples for the synthesis of C–S bonds are generally limited to the condensation reaction between a metal thiolate and an organic halide. Recent chemical approaches for C–S bond formation, based upon direct C–H bond functionalization and decarboxylative reactions, not only provide new insights into the mechanistic understanding of C–S coupling reactions but also allow the synthesis of sulfur-containing compounds from more effective synthetic routes with high atom economy. This review intends to explore recent advances in C–S bond formation via C–H functionalization and decarboxylation, and the growing opportunities they present to the construction of complex chemical scaffolds for applications encompassing natural product synthesis, synthetic methodology development, and functional materials as well as nanotechnology.

Recent advances in C–S bond formation via C–H bond functionalization and decarboxylation

Synthesis of imidazo[1,2-a]pyridines: a decade update.

Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

An unprecedented sulfenylation of indoles with sulfonyl hydrazides proceeds through the cleavage of the sulfur—oxygen and the sulfur—nitrogen bond.

Iodine-catalyzed regioselective sulfenylation of indoles with sulfonyl hydrazides.

Dimethyl sulfoxide (DMSO) is one of the most commonly applied organic solvents in chemical transformations and is utilized widely in industrial processes as well. During the past decades, numerous procedures using DMSO as a reaction reagent have been developed and published. In this review, the main developments on the employment of DMSO as sources of Me, SMe, SO2Me, as an oxidant etc. have been summarized and discussed.

The Applications of Dimethyl Sulfoxide as Reagent in Organic Synthesis

Iodine-catalyzed oxidative system for 3-sulfenylation of indoles with disulfides using DMSO as oxidant under ambient conditions in dimethyl carbonate

Aerobic Multicomponent Tandem Synthesis of 3-Sulfenylimidazo[1,2-a]pyridines from Ketones, 2-Aminopyridines, and Disulfides

Both aryl and alkyl disulfides are employed as sulfanylation reagents to give the desired products in good yields under the optimized reaction conditions.

Iodine‐Catalyzed Selective Synthesis of 2‐Sulfanylphenols via Oxidative Aromatization of Cyclohexanones and Disulfides

The simple method allows an efficient access to sulfurated indole derivatives of medicinal interest.

Copper(I) Iodide Catalyzed 3-Sulfenylation of Indoles with Unsymmetric Benzothiazolyl-Containing Disulfides at Room Temperature.

This protocol is also amenable to the preparation of 3-selenated imidazopyridines and works even without the presence of a disulfide or diselenide giving high flexibility of the substituent in 3-position.

Wenlei Ge

Papers

Iodine-catalyzed oxidative system for 3-sulfenylation of indoles with disulfides using DMSO as oxidant under ambient conditions in dimethyl carbonate

Aerobic Multicomponent Tandem Synthesis of 3-Sulfenylimidazo[1,2-a]pyridines from Ketones, 2-Aminopyridines, and Disulfides

Iodine‐Catalyzed Selective Synthesis of 2‐Sulfanylphenols via Oxidative Aromatization of Cyclohexanones and Disulfides

Copper(I) Iodide Catalyzed 3-Sulfenylation of Indoles with Unsymmetric Benzothiazolyl-Containing Disulfides at Room Temperature.

Aerobic Multicomponent Tandem Synthesis of 3‐Sulfenylimidazo[1,2‐a]pyridines from Ketones, 2‐Aminopyridines, and Disulfides.