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  • Title: Bismuth-based cyclic synthesis of 3,5-di-tert-butyl-4-hydroxybenzoic acid via the oxyarylcarboxy dianion, (O2CC6H2(t)Bu2O)2-.
    Author: Kindra DR, Evans WJ.
    Journal: Dalton Trans; 2014 Feb 28; 43(8):3052-4. PubMed ID: 24336959.
    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 Bi(3+) complex, Ar'BiCl2, of the NCN pincer ligand, Ar' = 2,6-(Me2NCH2)2C6H3. Complexes of the recently discovered oxyaryl dianion, (C6H2(t)Bu2-3,5-O-4)(2-), and the oxyarylcarboxy dianion, [O2C(C6H2(t)Bu2-3,5-O-4)](2-), are intermediates in the process. Further studies of the oxyarylcarboxy dianion in Ar'Bi[O2C(C6H2(t)Bu2-3,5-O-4)-κ(2)O,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.
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