Cobalt-promoted synthesis of sulfurated oxindoles via radical annulation of N -arylacrylamides with disulfides

An efficient radical annulation of N -arylacrylamides with disulfides is developed for the synthesis of sulfurated oxindoles. The reaction occurs in a facile manner using CoBr 2 as both an initiator and a promoter for the first time and (NH 4 ) 2 S 2 O 8 as the oxidant. By controlling the CoBr 2 /(N...

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Veröffentlicht in:Organic & biomolecular chemistry 2022-08, Vol.20 (32), p.6423-6431
Hauptverfasser: Cheng, Fei, Bai, Xue, Sun, Qi-Wen, Zhu, Gao-Feng, Dong, Yong-Xi, Yang, Yuan-Yong, Gao, Xiu-Li, Guo, Bing, Tang, Lei, Zhang, Ji-Quan
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Sprache:eng
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Zusammenfassung:An efficient radical annulation of N -arylacrylamides with disulfides is developed for the synthesis of sulfurated oxindoles. The reaction occurs in a facile manner using CoBr 2 as both an initiator and a promoter for the first time and (NH 4 ) 2 S 2 O 8 as the oxidant. By controlling the CoBr 2 /(NH 4 ) 2 S 2 O 8 ratio, a wide range of sulfurated and brominated/sulfurated oxindoles are selectively prepared in good to excellent yields. The present protocol is simple and highly atom economical, and can tolerate a broad range of substrates.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00877g