Recent Advances in the Electrochemical Synthesis of Organosulfur Compounds

Abstract

Organosulfur compounds are being widely used in medicinal chemistry, as well as in organic transformations and in synthetic applications. Because of their interest in many areas, the development of sustainable and green synthetic methods to access various organosulfur compounds has a high influence on the chemistry community. Electroorganic synthesis has become a very valuable methodology for the synthesis of organosulfur compounds during the last decade. The use of electrochemical technology offers a green, sustainable and safe alternative to prepare and modify such compounds. This review summarises recent developments in the preparation of organosulfur compounds such as sulfoxides, sulfones, sulfinic esters, sulfonamides, thiosulfonates, sulfonyl fluorides and sulfoximines under electrochemical reaction conditions.

Flow Electrosynthesis of Sulfoxides, Sulfones, and Sulfoximines without Supporting Electrolytes

“…34,35 We saw this as an opportunity to further improve and simplify the oxidation methodologies of organosulfur compounds. 36 In this work, we report a green synthesis method of sulfoxides, sulfones, and sulfoximines without any additional supporting electrolytes through a controlled current using an electrochemical flow reactor attached to a fully automated system. Unique features of the Vapourtec automatic flow system with an integrated electrochemical ion microflow reactor speed up the reaction, while largely reducing the amount of manpower needed to execute the reactions.…”

“…In an extension of our previous efforts toward the development of flow tools and techniques to implement flow transformations, , we recently have reported a reaction without using a supporting electrolyte and disclosed the first use of an integrated flow electrochemical reactor in an automated way. , We saw this as an opportunity to further improve and simplify the oxidation methodologies of organosulfur compounds …”

Sulfoxide and Sulfone Synthesis via Electrochemical Oxidation of Sulfides

“…With the renewed interest in electrochemistry as a useful synthetic tool over the past decade, it has been increasingly explored for the development of various synthetic methodologies because it allows for the control of redox chemistry under mild conditions …”

Anodic Dehydrogenative Cyanamidation of Thioethers: Simple and Sustainable Synthesis of N‐Cyanosulfilimines

“…[14][15][16][17][18][19] Also, due to many variable parameters in electrosynthesis, such as electrode material, electrolyte, current density, or the use of a mediated or direct process, electroorganic reactions are selective and could lead to products which were otherwise not accessible. [16,[18][19][20]21] As electroorganic synthesis is a very useful tool in the oxidation of sulfur-containing compounds, [22] there is previous work on the electrochemical synthesis of sulfoximines. First progress was made in 2002 by Yudin and co-workers, [23] who found a way for the imination of sulfoxides using N-aminophtalimide under potentiostatic conditions in a divided cell at a Pt anode.…”