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Synthesis 2023; 55(18): 2799-2816
DOI: 10.1055/a-2096-4349
DOI: 10.1055/a-2096-4349
review
Special Issue Electrochemical Organic Synthesis
Progress in S–X Bond Formation by Halogen-Mediated Electrochemical Reactions
This work was financially supported by the Guangxi Science and Technology Base and Special Talents (Guike AD23026279), the Science and Technology Program of Hunan Province (2021RC2079), the China Postdoctoral Science Foundation (2022M720541 and 2022T150075), the Tianjin Synthetic Biotechnology Innovation Capacity Improvement Project (TSBICIP-CXRC-038), Start-up Funding for Scientific Research of Nanning Normal University (86612345) and the BAGUI Scholars Program of Guangxi Province of China.
Abstract
Sulfur-containing compounds are very common and important heteroatom skeletons and are widely found in natural products, pharmaceuticals and bioactive compounds. Moreover, the development of synthetic routes to organosulfur compounds has attracted considerable attention due to their wide range of applications in organic chemistry, the pharmaceutical industry and in materials science. As one of most powerful, green and eco-friendly research areas, organic electrosynthesis, in contrast to conventional organic synthesis, can avoid the use of harmful stoichiometric external oxidants or reductants. Importantly, halide salts are widely used as supporting electrolytes and redox catalysts in indirect electrosynthesis to avoid the limitations imposed by high overpotentials in direct electrosynthesis. In recent years, significant progress has been made on the halogen-mediated electrosynthesis of organosulfur compounds. In this review, the scope, limitations and mechanisms of halogen-mediated electrochemical transformations of sulfur-containing compounds are presented and discussed.
1 Introduction
2 S–C Bond Formation
2.1 Organic Thiocyanates
2.2 Sulfonyl Compounds
2.3 Other Sulfides
3 Formation of Other S–X (X = N, O, S, P) Bonds
4 Conclusion and Outlook
Key words
organosulfur compounds - electrosynthesis - halogen-mediated - eco-friendly - sulfonyl compounds - organic thiocyanatesPublication History
Received: 28 March 2023
Accepted after revision: 19 May 2023
Accepted Manuscript online:
19 May 2023
Article published online:
27 June 2023
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