Visible-light-induced sequential sulfonylation/hydroxylation of allylacetamides leading to β-tert-hydroxy sulfones

A mild method for the sequential sulfonylation/hydroxylation process of allylacetamides has been developed, in which sulfonyl radicals can be generated from easily available arylsulfinic acids by using eosin Y as an organic photocatalyst under visible-light irradiation. The new C–O and C–S bonds can...

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Bibliographic Details
Published in:Tetrahedron 2021-03, Vol.83, p.131999, Article 131999
Main Authors: Qian, Zhu-Ming, Zuo, Kai-Li, Guan, Zhi, He, Yan-Hong
Format: Article
Language:English
Subjects:
Eosin Y
Hydroxylation
Photoredox catalysis
Sulfonylation
β-hydroxysulfone
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Summary:A mild method for the sequential sulfonylation/hydroxylation process of allylacetamides has been developed, in which sulfonyl radicals can be generated from easily available arylsulfinic acids by using eosin Y as an organic photocatalyst under visible-light irradiation. The new C–O and C–S bonds can be constructed in one-pot to directly access β-tert-hydroxy sulfone derivatives. A novel visible-light-induced sequential sulfonylation/hydroxylation reaction for the synthesis of β-tert-hydroxy sulfone derivatives in air atmosphere at room temperature is described for the first time. [Display omitted] •A mild method for the sequential sulfonylation/hydroxylation of allylacetamides has been developed.•Sulfonyl radicals can be generated from easily available arylsulfinic acids.•Eosin Y was used as an organic photocatalyst under visible-light irradiation.•C-O and C-S bonds can be constructed in one-pot to directly access β-tert-hydroxy sulfone derivatives.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2021.131999