Issue 8, 2014

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

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−

Supplementary files

Article information

Article type
Communication
Submitted
11 Nov 2013
Accepted
29 Nov 2013
First published
02 Dec 2013

Dalton Trans., 2014,43, 3052-3054

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements