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Facile and Selective Cross‐Coupling of Phenols Using Selenium Dioxide
Author(s) -
Quell Thomas,
Beiser Nicole,
Dyballa Katrin M.,
Franke Robert,
Waldvogel Siegfried R.
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600886
Subject(s) - chemistry , selenium , phenols , halogen , alkyl , alkoxy group , oxidative phosphorylation , oxidative coupling of methane , organic chemistry , combinatorial chemistry , biochemistry , methane
Nonsymmetric biphenols are important structural motifs in organic chemistry. Therefore, an easy and versatile protocol for oxidative cross‐coupling is essential to generate these so‐called “privileged ligands”. We developed an efficient and selective oxidative pathway to synthesize 2,2′‐biphenols as well as 2,4′‐ and 4,4′‐biphenols. The use of selenium dioxide, a stable, powerful, and commercially available oxidizer, in 1,1,1,3,3,3‐hexafluoroisopropanol allowed the oxidative coupling of alkyl‐, alkoxy‐, and halogen‐substituted phenols.