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Issue 34, 2015
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N-heterocyclic carbene–palladium(II)-1-methylimidazole complex catalyzed α-arylation reactions of tetralones with aryl chlorides and further transformation of the products

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Abstract

NHC–Pd(II)–Im complex 1 has proven to be an efficient catalyst in the reaction between tetralones 2 and aryl chlorides 3, giving the α-arylated tetralones 4 in good to high yields. In addition, if the above reaction mixture was exposed to air at room temperature for another 3 h, the normal α-arylated products 4 can be fully oxidized to 2-aryl-2′-hydroxytetralones 6 in good yields in a one-pot procedure. Furthermore, if the reaction mixture containing the oxidized products 6 was treated with TsOH/toluene solution under reflux for 19 h, the final aromatized products, 2-aryl-naphthalen-1-ols 5 can be achieved in acceptable to moderate yields. All reactions can tolerate various substituents on the tetralones 2 and aryl chlorides 3, thus giving an efficient method for the α-arylation of tetralones and further transformation of the products, and also enriching the applications of NHC–Pd(II) complexes in organic synthesis.

Graphical abstract: N-heterocyclic carbene–palladium(ii)-1-methylimidazole complex catalyzed α-arylation reactions of tetralones with aryl chlorides and further transformation of the products

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Publication details

The article was received on 12 Jun 2015, accepted on 11 Jul 2015 and first published on 15 Jul 2015


Article type: Paper
DOI: 10.1039/C5OB01203A
Citation: Org. Biomol. Chem., 2015,13, 9012-9021

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    N-heterocyclic carbene–palladium(II)-1-methylimidazole complex catalyzed α-arylation reactions of tetralones with aryl chlorides and further transformation of the products

    H. Yin, X. Lin, S. Li and L. Shao, Org. Biomol. Chem., 2015, 13, 9012
    DOI: 10.1039/C5OB01203A

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