5048-02-2Relevant articles and documents
Chemoselective oxidative generation of ortho-quinone methides and tandem transformations
Ishihara, Kazuaki,Kondo, Ryutaro,Nishioka, Kohei,Uyanik, Muhammet
, p. 353 - 362 (2020/04/09)
ortho-Quinone methides are useful transient synthetic intermediates in organic synthesis. These species are most often generated in situ by the acid- or base-mediated transformation of phenols that have been pre-functionalized at a benzylic position, or by biomimetic oxidation of the corresponding ortho-alkylphenols with metal oxidants or transition-metal complexes. Here we describe a method for the transition-metal-free oxidative generation of o-QMs from ortho-alkylarenols, using hypoiodite catalysis under nearly neutral conditions, which can then be applied in one-pot tandem reactions. This method for the chemoselective oxidative generation of ortho-quinone methides may prove superior to previous methods with respect to environmental issues and scope, and can be applied to various tandem reactions such as inter- or intramolecular [4 + 2] cycloaddition, oxa-6π-electrocyclization, conjugate addition and spiroepoxidation. [Figure not available: see fulltext.].
Selective benzylic C-C coupling catalyzed by a bioinspired dicopper complex
Prokofieva, Angelina,Prikhod'ko, Alexander I.,Dechert, Sebastian,Meyer, Franc
, p. 1005 - 1007 (2008/09/21)
A highly preorganized bioinspired dicopper complex with imidazole ligation catalyzes the selective benzylic para-C-H activation of 2,4,6-trimethylphenol under aerobic conditions, yielding either the stilbenequinone or 4-methoxymethyl-2,6-dimethylphenol depending on the solvent used. The Royal Society of Chemistry.
Copper-mediated selective oxidation of a C-H bond
Boldron, Christophe,Gamez, Patrick,Tooke, Duncan M.,Spek, Anthony L.,Reedijk, Jan
, p. 3585 - 3587 (2007/10/03)
(Chemical Equation Presented) An environmentally friendly procedure has been developed for the oxidation of 2,4,6-trimethylpheriol (TMP) at the para Csp3-H bond. Upon reaction with H2O2 in the presence of catalytic amounts of CuII and neocuproine in methanol at 65°C, 4-(methoxymethyl)-2,6-dimethylphenol (MDP) or 4-hydroxy-3,5- dimethylbenzaldehyde (HDB) is formed (see reaction).