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This strategy is achieved through visible light\u2010mediated late\u2010stage functionalization of the sulfur atoms of mercaptopurines. The <jats:italic>in\u2005situ<\/jats:italic>\u2010generated disulfide was proposed as the pivotal neutral intermediate for this transformation. We present herein a novel photo\u2010mediated homolytic C\u2212S bond formation for the preparation of alkylthiopurines and alkylthiopurine nucleosides. Despite the presence of reactive sites for the Minisci reaction, chemoselective <jats:italic>S<\/jats:italic>\u2010alkylation remained the predominant pathway. This method allows for the late\u2010stage introduction of a broad spectrum of alkyl groups onto the sulfur atom of unprotective mercaptopurine derivatives, encompassing 2\u2010, 6\u2010, and 8\u2010mercaptopurine rings. Organoborons serve as efficient and eco\u2010friendly alkylating reagents, providing advantages in terms of readily availability, stability, and reduced toxicity. Further derivatization of the thioetherified nucleosides, together with anti\u2010tumor assays, led to the discovery of potent anti\u2010tumor agents with an IC<jats:sub>50<\/jats:sub> value reaching 6.1\u2005\u03bcM (Comp. <jats:bold>31<\/jats:bold> for Jurkat).<\/jats:p>","DOI":"10.1002\/chem.202401774","type":"journal-article","created":{"date-parts":[[2024,6,26]],"date-time":"2024-06-26T11:31:58Z","timestamp":1719401518000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Visible Light\u2010Mediated Late\u2010Stage Thioetherification of Mercaptopurine Derivatives"],"prefix":"10.1002","volume":"30","author":[{"given":"Yuhua","family":"Ge","sequence":"first","affiliation":[{"name":"School of Chemistry and Chemical Engineering Southeast University  Nanjing 211189 P.\u2005R.China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yijiang","family":"Peng","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Southeast University  Nanjing 211189 P.\u2005R.China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ruoqian","family":"Xie","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering Southeast University  Nanjing 211189 P.\u2005R.China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yang","family":"Luo","sequence":"additional","affiliation":[{"name":"Shanghai Key Laboratory for Molecular Engineer of Chiral Drugs, School of Chemistry and Chemical Engineering Shanghai Jiao Tong University  Shanghai 200240 P.\u2005R. 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