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; Shun-Jun Ji

doi:10.1021/acs.orglett.0c01776

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

Org Lett. 2020 Jun 19;22(12):4908-4913. doi: 10.1021/acs.orglett.0c01776. Epub 2020 Jun 10.

Authors

Jian Li^{1

2}, Xin-Er Yang^{1

2}, Shan-Le Wang^{1

2}, Long-Long Zhang^{1

2}, Xiao-Zhou Zhou³, Shun-Yi Wang^{1

2}, Shun-Jun Ji^{1

2}

Affiliations

¹ Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.
² Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China.
³ Suzhou High School of Jiangsu Province, Suzhou 215000, China.

PMID: 32519870
DOI: 10.1021/acs.orglett.0c01776

Abstract

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 C_sp3-S or C_sp3-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.