Visible-Light-Promoted Cross-Coupling Reactions of 4‑Alkyl-1,4- dihydropyridines with Thiosulfonate or Selenium Sulfonate: A Unified Approach to Sulfides, Selenides, and Sulfoxides
Jian Li, Xin-Er Yang, Shan-Le Wang, Long-Long Zhang, Xiao-Zhou Zhou, Shun-Yi Wang*（汪顺义）, and Shun-Jun Ji*（纪顺俊）
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science and Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China
Org. Lett.2020,22, 4908--4913
In this paper, a visible-light-promoted cross-coupling of 4-alkyl-1,4-dihydropyridines with thio-selenium sulfonates under transition-metal-free conditions is described. This strategy features easily available substrates, mild reaction conditions, high yields, and high chemoselectivity. A novel synthetic route for the construction of a sulfide or selenide Csp3–S or Csp3–Se bond under transition-metal-free conditions without an additive oxidant or base is developed. This method is well extended to the synthesis of a class of thiolated or selenylated glycosides that has not been explored before. Sulfoxides were also successfully chemoselectively observed via a facile variation of the atmosphere under photocatalyzed conditions.