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The activation and transformation of organic chemical bonds is a fundamental scientific problem. In the past several decades, C–S bond cleavage for the construction of C–C and C–heteroatom bonds has received tremendous attention in organic chemistry. Although significant progress has been made in the field of transition metal strategies, a variety of novel transition-metal-free strategies have also been developed using halogenated reagents, oxidants, acids, and bases. Moreover, organic photochemical and electrochemical methods have also been developed to achieve transition-metal-free C–S bond cleavage of organosulfur compounds. To date, however, no comprehensive review of transition-metal-free strategies has been reported. Therefore, we herein provide a comprehensive review of the major advances in the field of the transition-metal-free C–S bond cleavage and transformation of organosulfur compounds, including thioethers, sulfoxides, sulfones, thioacetals, sulfonium salts, and sulfur ylides. [ABSTRACT FROM AUTHOR]

A metal‐free C(sp3)−S bond cleavage of β‐alkylthio carbonyl compounds in the presence of Selectfluor is described. This novel strategy realizes the C−S bond cleavage and subsequent C−O bond formation, providing a facile and efficient method to construct different important β‐alkoxy carbonyl compounds with moderate to good yields and good functional groups tolerance. Moreover, our mechanistic studies also prove that two different mechanisms including the oxidant and thionium ion intermediate pathway may exist in this process. [ABSTRACT FROM AUTHOR]

Metal‐free and Selectfluor‐mediated C–S bond cleavage is described. This novel strategy provides a facile and efficient method to access important N‐substituted acrylamide and β‐aminopropanamide derivatives with good functional group tolerance and yields. [ABSTRACT FROM AUTHOR]