PulseExploreJournal ClubDebatesTrendingResearchersJournals
Instagram
HomeExploreJournal ClubTrending
Synapse
⌘+K
Synapse
October 10, 2025The Journal of Organic Chemistry2 citations

Photoredox-Catalyzed Hydrofluoromethylthiolation of Unactivated Alkenes to Access Alkyl Di- and Trifluoromethyl Sulfides

View Full Paper
XFXiao-Qing FengLZLili ZengSXShi-Han Xu

Key Points

  • This method achieves up to 93% yield for the synthesis of alkyl di- and trifluoromethyl sulfides.
  • With 47 examples tested, the reaction demonstrates excellent chemo- and regioselectivity under mild conditions.
  • The approach uses organic photocatalysis to eliminate the need for metal and oxidants, enhancing environmental compatibility.
  • Preliminary studies suggest a radical pathway is involved, pointing to potential applications in drug functionalization.

Abstract

Herein, a visible-light-induced photocatalytic hydrofluoromethylthiolation of unactivated alkenes for the efficient construction of aliphatic di- and trifluoromethyl sulfides (47 examples, up to 93% yield) is described. In contrast to previous methods, this protocol eliminates the need for transition metals and oxidants, employing mild and environmentally benign organic photocatalysis instead. This transformation features operational simplicity, excellent chemo- and regioselectivity, and high compatibility with unactivated alkenes while demonstrating effectiveness for late-stage functionalization of commercially available drug derivatives. Preliminary mechanistic studies suggest that a radical pathway is involved in the catalytic cycle.

Ask AI
Helpful
Bookmark
Share
View Full Paper

Cite This Study

Feng et al. (2025) studied this question.

synapsesocial.com/papers/68e865117ef2f04ca37e4dc1https://doi.org/10.1021/acs.joc.5c01829
Ask AI
Helpful
Bookmark
Share
View Full Paper