Disulfide‐Directed C–H Hydroxylation for Synthesis of Sulfonyl Diphenyl Sulfides and 2‐(Phenylthio)phenols with Oxygen as Oxidant

Compared to N, O and P as directing functional atoms, the application of directing group containing sulfur atoms for transition metal‐catalyzed C–H activation is much more difficult for the known reason (some metal catalysts are easily poisoned by sulfur). Here, the disulfide‐directed C–H activation...

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Veröffentlicht in:Advanced synthesis & catalysis 2017-03, Vol.359 (5), p.779-785
Hauptverfasser: Wang, Long, Xie, Yi‐Bi, Huang, Nian‐Yu, Zhang, Nuo‐Nuo, Li, De‐Jiang, Hu, Yu‐Lin, Liu, Ming‐Guo, Li, Dong‐Sheng
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Sprache:eng
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Zusammenfassung:Compared to N, O and P as directing functional atoms, the application of directing group containing sulfur atoms for transition metal‐catalyzed C–H activation is much more difficult for the known reason (some metal catalysts are easily poisoned by sulfur). Here, the disulfide‐directed C–H activation for thew synthesis of sulfonyl diphenyl sulfides was realized for the first time by a copper‐catalyzed, tandem, one‐step C–S coupling/hydroxylation of disulfides and arylboronic acids with oxygen as the oxidant. This method provides a mild and easy method for the synthesis of sulfonyl diphenyl sulfides and 2‐(phenylthio)phenol derivatives and avoids producing sulfoxides and sulfones under air conditions and elevated temperatures.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600861