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Issue 8, 2014
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Bismuth-based cyclic synthesis of 3,5-di-tert-butyl-4-hydroxybenzoic acid via the oxyarylcarboxy dianion, (O2CC6H2tBu2O)2−

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Abstract

3,5-Di-tert-butyl-4-hydroxybenzoic acid can be made under mild conditions in a cyclic process from carbon dioxide and 3,5-di-tert-butyl-4-phenol using bismuth-based C–H bond activation and CO2 insertion chemistry starting with the Bi3+ complex, Ar′BiCl2, of the NCN pincer ligand, Ar′ = 2,6-(Me2NCH2)2C6H3. Complexes of the recently discovered oxyaryl dianion, (C6H2tBu2-3,5-O-4)2−, and the oxyarylcarboxy dianion, [O2C(C6H2tBu2-3,5-O-4)]2−, are intermediates in the process. Further studies of the oxyarylcarboxy dianion in Ar′Bi[O2C(C6H2tBu2-3,5-O-4)-κ2O,O′], show that it undergoes decarboxylation upon reaction with I2 and it reacts with trimethylsilyl chloride to produce the trimethylsilyl ether of the trimethylsilyl ester of 3,5-di-tert-butyl-4-hydroxybenzoic acid and the Ar′BiCl2 starting material.

Graphical abstract: Bismuth-based cyclic synthesis of 3,5-di-tert-butyl-4-hydroxybenzoic acid via the oxyarylcarboxy dianion, (O2CC6H2tBu2O)2−

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Publication details

The article was received on 11 Nov 2013, accepted on 29 Nov 2013 and first published on 02 Dec 2013


Article type: Communication
DOI: 10.1039/C3DT53187B
Citation: Dalton Trans., 2014,43, 3052-3054
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    Bismuth-based cyclic synthesis of 3,5-di-tert-butyl-4-hydroxybenzoic acid via the oxyarylcarboxy dianion, (O2CC6H2tBu2O)2−

    D. R. Kindra and W. J. Evans, Dalton Trans., 2014, 43, 3052
    DOI: 10.1039/C3DT53187B

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