Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 1, Pages 300-303Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910830
Keywords
addition reactions; electron transfer; phenothiazine; photocatalysis; photochemistry
Categories
Funding
- Deutsche Forschungsgemeinschaft [Wa 1386/16-2]
- Landesgraduiertenstiftung Baden-Wurttemberg
- KIT
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SF6 was applied as pentafluorosulfanylation reagent to prepare ethers with a vicinal SF5 substituent through a one-step method involving photoredox catalysis. This method shows a broad substrate scope with respect to applicable alcohols for the conversion of alpha-methyl and alpha-phenyl styrenes. The products bear a new structural motif with two functional groups installed in one step. The alkoxy group allows elimination and azidation as further transformations into valuable pentafluorosulfanylated compounds. These results confirm that non-toxic SF6 is a useful SF5 transfer reagent if properly activated by photoredox catalysis, and toxic reagents are completely avoided. In combination with light as an energy source, a high level of sustainability is achieved. Through this method, the proposed potential of the SF5 substituent in medicinal chemistry, agrochemistry, and materials chemistry may be exploited in the future.
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