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Oxidative Coupling of Naphthols to Ketones: An Approach to 1,2‐Diketones
Author(s) -
Deb Mohit L.,
Saikia BShriya,
Rastogi Gaurav K.,
Baruah Pranjal K.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201702831
Subject(s) - catalysis , chemistry , oxidative coupling of methane , solvent , oxidative phosphorylation , oxygen , functional group , ketone , active oxygen , reaction mechanism , organic chemistry , medicinal chemistry , combinatorial chemistry , biochemistry , polymer
1,2‐Diketones are highly useful building blocks for the synthesis of pharmaceuticals, natural products and heterocycles. A simple and efficient route to 1,2‐diketones is developed here. The strategy involves coupling of naphthols to methyl ketones via oxidative C−H functionalization of methyl group of ketones. CuI (10 mol %) is used as catalyst and FeSO 4 .7H 2 O (10 mol %) as additive, both of which are environmentally benign and cheap. The reaction is carried out in DMSO solvent at 120 o C for 8–10 h. Little amount of 1,1′‐bi‐2‐naphthol (BINOL) is also formed as side product. A tentative mechanism is proposed for the reaction which demonstrates a free‐radical pathway. Although Cu(I) is used as catalyst, however, the in situ generated Cu(II) behaves as the active catalytic species. Aerial oxygen acts as the oxygen source for the newly formed carbonyl functional group.