Synthesis 2019; 51(10): 2230-2236
DOI: 10.1055/s-0037-1611211
paper
© Georg Thieme Verlag Stuttgart · New York

Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck–Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates

Dmitry Dar’in
a   Saint Petersburg State University, Saint Petersburg 199034, Russian Federation   Email: m.krasavin@spbu.ru
,
Grigory Kantin
a   Saint Petersburg State University, Saint Petersburg 199034, Russian Federation   Email: m.krasavin@spbu.ru
,
Olga Bakulina
a   Saint Petersburg State University, Saint Petersburg 199034, Russian Federation   Email: m.krasavin@spbu.ru
,
Raivis Žalubovskis
b   Latvian Institute of Organic Synthesis, Riga 1006, Latvia
,
Mikhail Krasavin*
a   Saint Petersburg State University, Saint Petersburg 199034, Russian Federation   Email: m.krasavin@spbu.ru
› Author Affiliations
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’).
Further Information

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.

Supporting Information