Metal-Free C−S Bond Cleavage

Metal-Free C−S Bond Cleavage

Author: European Journal of Organic Chemistry

The activation and transformations of C–S bonds in thioether compounds is useful, e.g., in the petroleum industry and in organic chemistry. Such reactions usually rely on the insertion of a transition-metal catalyst into the C−S bond, leading to C−S bond cleavage.

Ke Yang, Yi Li, Zhiyan Ma, Long Tang, Yue Yin, Hao Zhang, Zhengyi Li and Xiaoqiang Sun, Changzhou University, China, have developed an efficient metal-free C−S bond cleavage process. The method allows the team to access different  β-aminopropanamide and acrylamide derivatives. Using Selectfluor as an “F+” reagent, a variety of N-substituted acrylamides were synthesized from N-substituted 3-methylthiopropanamides in 1,4‐dioxane (reaction pictured). The products were obtained in good to excellent yields.

The reaction can also be used to convert the thioethers to amine derivatives: When different N-substituted 3-methylthiopropanamides were reacted with amines in the presence of Selectfluor, N-substituted β-aminopropanamides were obtained in moderate to good yields.

Mechanistic investigations indicate that the N-substituted 3-methylthiopropanamides are converted the corresponding thionium intermediates or sulfoxides in the presence of Selectfluor, both of which can then be further transformed into N-substituted acrylamides and β-aminopropanamides.


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