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Photoredox Catalytic ?-Alkoxypentafluorosulfanylation of ?-Methyl- and ?-Phenylstyrene Using SF6.

ABSTRACT: 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 ?-methyl and ?-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.

SUBMITTER: Rombach D

PROVIDER: S-EPMC6973110 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Photoredox Catalytic α-Alkoxypentafluorosulfanylation of α-Methyl- and α-Phenylstyrene Using SF6.

Rombach David D Wagenknecht Hans-Achim HA

Angewandte Chemie (International ed. in English) 20191126 1

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 α-methyl and α-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 penta ...[more]

PMID: 31680388

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