Recent Developments in Selenylation and Thiolation of Alkenes via Three-component Reactions

Alkenes are valuable feedstocks in organic synthesis. Selenium or sulfur-containing coumpounds with a neighboring functional group can be easily prepared by direct difunctionalization of alkenes via three-component reactions. It will reduce the number of steps and waste generation, and form complicated molecules from simple starting materials. Herein, recent developments (2013-2022) have been summarized via two categories: (1) selenylation via seleniranium intermediates or Se-centered radicals; (2) thiolation with more diverse mechanisms and products Reactions with electron-rich arenes, alcohols, water, acids, NaN3, amines, KSCN, and sulfamides, TMSNCS, TMSN3, Et3N center dot 3HF, SOCl2, HCl, NFSI, (BuONO)-Bu-t, pyridinium salts, (BuOOH)-Bu-t, ArN2BF4, CO2, CO, O-2, CF3SO2Cl, R2P(O) H, (RO)(2)P(O)SH, (RO)(2)P(O)OH et al will be discussed. We hope this review will do help for future research in this area. 1. Introduction 2. Selenylation 2.1. Reactions via Seleniranium Intermediates 2.2. Reactions via Se-Radicals 3. Thiolation 3.1. Synthesis of Sulfides 3.2. Synthesis of Sulfoxides 3.3. Synthesis of Sulfones 4. Conclusions and Outlook

Automated summary

Alkenes are valuable in organic synthesis, and they can be easily transformed into selenium or sulfur-containing compounds with a neighboring functional group via three-component reactions. This approach reduces the number of steps and waste generation while enabling the formation of complex molecules from simple starting materials. Recent developments in selenylation and thiolation reactions are summarized in this review, including various reactants such as electron-rich arenes, alcohols, water, acids, and other compounds. This review aims to provide insights for future research in this area.