Denitrative thiocyanation of β-nitrostyrenes through visible light photoredox catalysis: An easy access to (E)-vinyl thiocyanates

[Display omitted] •Metal-free one-pot protocol for the synthesis of vinyl thiocyanates.•Denitrative thiocyanation of β-nitrostyrenes.•Visible light photoredox catalysis with eosin Y under aerobic conditions.•Radical pathway for sp2 C-SCN bond formation. Eosin Y efficiently catalyzes the aerobic visi...

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Bibliographic Details
Published in:Tetrahedron letters 2020-11, Vol.61 (46), p.152505, Article 152505
Main Authors: Kapoor, Ritu, Chawla, Ruchi, Yadav, Lal Dhar S.
Format: Article
Language:English
Subjects:
(E)-Vinyl thiocyanates
Photoredox catalysis
Thiocyanation
β-Nitrostyrenes
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Summary:[Display omitted] •Metal-free one-pot protocol for the synthesis of vinyl thiocyanates.•Denitrative thiocyanation of β-nitrostyrenes.•Visible light photoredox catalysis with eosin Y under aerobic conditions.•Radical pathway for sp2 C-SCN bond formation. Eosin Y efficiently catalyzes the aerobic visible light mediated formation of sp2 C-SCN bond through denitrative reaction of β-nitrostyrenes with ammonium thiocyanate in acetonitrile to afford (E)-vinyl thiocyanates in good to excellent yields. Metal-free conditions, use of sustainable resources (visible light and air) and ambient temperature are the exclusive attributes of the present protocol.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.152505