Recent Metal-Catalyzed Methods for Thioether Synthesis

Abstract

This review summarizes the more recent methods for the synthesis of thioethers using homogeneous metals as catalysts. The thioether moiety can be found in numerous compounds for pharmaceutical, agricultural or material applications and it is therefore important to develop new, efficient methods for their synthesis. The recent efforts in this field focus on the use of non-precious metal catalysts, as well as on the development of new bond-forming processes. 1 Introduction 2 Cross-couplings 3 C-H Activation 4 Hydrothiolation 5 Carbothiolation 6 Miscelaneous 7 Conclusion

Nickel Catalyzed Cross-Coupling of Aryl and Alkenyl Triflates with Alkyl Thiols

“…Thioethers are common motifs in agrochemicals, materials, and pharmaceutical compounds . They can be conveniently synthesized via a variety of transformations . One of the most prominent and versatile methods is the metal-catalyzed coupling of thiols with aryl and alkenyl (pseudo)­halides, also referred to as Migita-coupling .…”

“…3 They can be conveniently synthesized via a variety of transformations. 4 One of the most prominent and versatile methods is the metalcatalyzed coupling of thiols with aryl and alkenyl (pseudo)halides, also referred to as Migita-coupling. 5 Catalysts for this transformation are often based on palladium, but nickel as a lowcost and abundant metal has developed into an attractive alternative.…”

Recent Advances in Nonprecious Metal Catalysis

“…Thioethers are functional groups often present in therapeutic agents and are also frequently integrated into reagents or organocatalysts for various synthetic methodologies . Most approaches to preparing thioethers involve conventional alkylation, photocatalysis, or metal-catalyzed couplings with thiols. Because of the undesirable physical properties associated with thiols, it is more attractive to use higher oxidation states of sulfur such as sulfinic acids.…”

Dehydroaromatization of Indolines and Cyclohexanones with Thiol Access to Aryl Sulfides under Basic Conditions

“…Traditionally, the preparation of aryl sulfides involves the coupling of aryl (pseudo)­halides, boronic acids, and carboxylic acid derivatives with aryl thiols performed under transition metal catalysis or under transition metal-free conditions (Scheme a) . However, most of the reactions require prefunctionalization of starting materials and generate undesired byproducts that jeopardize the overall efficiency of these methods.…”