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DOI: 10.1055/s-0037-1611211
Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck–Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates
This work was supported by the Russian Foundation for Basic Research (project grant 18-515-76001) under «ERA.Net RUS plus» joint program grant RUS_ST2017-309 and State Education Development Agency of Republic of Latvia (‘THIOREDIN’).Publication History
Received: 27 December 2018
Accepted after revision: 29 January 2019
Publication Date:
25 February 2019 (online)
Abstract
For the preparation of compound libraries of Michael acceptors with tunable reactivity toward nuclophilic selenocysteine residue of thioredoxin reductase, a range of 3-arylglutaconic acids were required. The existing methods at the time had limited scope or involved several steps. A hitherto undescribed protocol for direct palladium(II) acetate-catalyzed arylation of glutaconic acid dimethyl ester at position 3 has been developed with a diverse set of arenediazonium tosylates followed by hydrolysis. This generally good-yielding two-step sequence displayed a propensity to deliver E-configured coupling products while compounds mostly featured in the literature were predominantly Z-configured. The possibility for preparing a library of 4-arylpyridine-2,6(1H,3H)-diones has been exemplified.
Key words
arylpent-2-enedioic acids - glutaconic acid - diazonium tosylate - Pd-catalyzed coupling - regiospecificity - ester hydrolysis - imide synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611211. Copies of 1H and 13C NMR spectra are provided.
- Supporting Information
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