4.8 Article

Photocatalytic C-H Trifluoromethylthiolation by the Decatungstate Anion

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ORGANIC LETTERS
卷 23, 期 15, 页码 5729-5733

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01870

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  1. Deutsche Forschungsgemeinschaft (DFG) [KO 1537/18-1]
  2. Fonds der Chemischen Industrie (FCI)
  3. Studienstiftung des deutschen Volkes

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A broadly applicable method for trifluorome-thylthiolation of various types of C-H bonds using decatungstate anion as the sole catalyst has been developed, achieving good regioselectivities in 40 examples, including natural product derivatization. Additionally, SCF3-drug analogues were synthesized by subsequent functionalization of the SCF3 products, highlighting the importance of this photocatalyzed C-H functionalization.
A broadly applicable method for the trifluorome-thylthiolation of methylene C(sp(3))-H, methine C(sp(3))-H, alpha-oxygen C(sp(3))-H, and formyl C(sp(2))-H bonds is presented using the decatungstate anion as the sole catalyst. By adjusting the substrate ratio and reaction concentration, this method was applied to 40 examples in good regioselectivities, including the derivatization of natural products. Furthermore, SCF3-drug analogues were synthesized by subsequent functionalization of the SCF3 products, highlighting the importance of this photocatalyzed C-H functionalization.

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