Copper-Catalyzed Thiolation of Hydrazones with Sodium Sulfinates: A Straightforward Synthesis of Benzylic Thioethers

Copper-Catalyzed Thiolation of Hydrazones with Sodium Sulfinates: A Straightforward Synthesis of Benzylic Thioethers

A facile and sustainable protocol for the thiolation of hydrazones with sodium sulfinates has been developed in the presence of CuBr2 and DBU in DMF to afford diverse benzylic thioethers. Control experiments reveal a radical pathway involving a thiyl radical as a key intermediate.

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Veröffentlicht in:Journal of organic chemistry 2023-01, Vol.88 (1), p.475-482
Hauptverfasser: Pandey, Anand Kumar, Chand, Shiv, Sharma, Anup Kumar, Singh, Krishna Nand
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Copper
Hydrazones
Sodium
Sulfides
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Zusammenfassung:A facile and sustainable protocol for the thiolation of hydrazones with sodium sulfinates has been developed in the presence of CuBr2 and DBU in DMF to afford diverse benzylic thioethers. Control experiments reveal a radical pathway involving a thiyl radical as a key intermediate.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02451