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Oxidant‐Controlled Catalytic Transformations of Phenols with Unexpected Cleavage of Aromatic Rings
Author(s) -
Li Wei,
Song Feijie,
You Jingsong
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501826
Subject(s) - phenols , chemistry , oxidative coupling of methane , catalysis , phenol , cleavage (geology) , oxidative cleavage , ring (chemistry) , organic chemistry , bond cleavage , combinatorial chemistry , materials science , fracture (geology) , composite material
Oxidative transformations of phenols have attracted significant attention of chemists due to their importance in biological process and organic synthesis. In contrast to the relatively well‐developed oxygenation and coupling reactions of phenols, the highly efficient and selective oxidative ring cleavage of phenols is under‐represented. This work describes a novel CuCl‐catalyzed tandem homocoupling/skeletal rearrangement of phenols that realizes the cleavage of the phenol ring by using air or Ag 2 CO 3 as the oxidant. Interestingly, simply changing the oxidant to K 2 S 2 O 8 results in the oxidative coupling/cyclization of phenols to give dibenzofurans. These results set an important precedent of oxidant‐controlled catalytic transformations of phenols.