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Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck-Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates. / Dar'In, Dmitry; Kantin, Grigory; Bakulina, Olga; Žalubovskis, Raivis; Krasavin, Mikhail.

In: Synthesis (Germany), Vol. 51, No. 10, 05.2019, p. 2230-2236.

Research output: Contribution to journal › Article › peer-review

Harvard

Dar'In, D, Kantin, G, Bakulina, O, Žalubovskis, R & Krasavin, M 2019, 'Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck-Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates', Synthesis (Germany), vol. 51, no. 10, pp. 2230-2236. https://doi.org/10.1055/s-0037-1611211

APA

Dar'In, D., Kantin, G., Bakulina, O., Žalubovskis, R., & Krasavin, M. (2019). Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck-Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates. Synthesis (Germany), 51(10), 2230-2236. https://doi.org/10.1055/s-0037-1611211

Vancouver

Dar'In D, Kantin G, Bakulina O, Žalubovskis R, Krasavin M. Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck-Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates. Synthesis (Germany). 2019 May;51(10):2230-2236. https://doi.org/10.1055/s-0037-1611211

Author

Dar'In, Dmitry ; Kantin, Grigory ; Bakulina, Olga ; Žalubovskis, Raivis ; Krasavin, Mikhail. / Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck-Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates. In: Synthesis (Germany). 2019 ; Vol. 51, No. 10. pp. 2230-2236.

BibTeX

@article{66a24cdec4ad40c3bf3b354b1f85b062,
title = "Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck-Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates",
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(1 H,3 H)-diones has been exemplified.",
keywords = "arylpent-2-enedioic acids, diazonium tosylate, ester hydrolysis, glutaconic acid, imide synthesis, Pd-catalyzed coupling, regiospecificity, TRIFLUOROMETHYLATED TERTIARY THIOETHERS, DIELS-ALDER REACTIONS, DIAZONIUM SALTS, SULFA-MICHAEL ADDITION",
author = "Dmitry Dar'In and Grigory Kantin and Olga Bakulina and Raivis {\v Z}alubovskis and Mikhail Krasavin",
year = "2019",
month = may,
doi = "10.1055/s-0037-1611211",
language = "English",
volume = "51",
pages = "2230--2236",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "10",

}

RIS

TY - JOUR

T1 - Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck-Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates

AU - Dar'In, Dmitry

AU - Kantin, Grigory

AU - Bakulina, Olga

AU - Žalubovskis, Raivis

AU - Krasavin, Mikhail

PY - 2019/5

Y1 - 2019/5

N2 - 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(1 H,3 H)-diones has been exemplified.

AB - 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(1 H,3 H)-diones has been exemplified.

KW - arylpent-2-enedioic acids

KW - diazonium tosylate

KW - ester hydrolysis

KW - glutaconic acid

KW - imide synthesis

KW - Pd-catalyzed coupling

KW - regiospecificity

KW - TRIFLUOROMETHYLATED TERTIARY THIOETHERS

KW - DIELS-ALDER REACTIONS

KW - DIAZONIUM SALTS

KW - SULFA-MICHAEL ADDITION

UR - http://www.scopus.com/inward/record.url?scp=85065177733&partnerID=8YFLogxK

U2 - 10.1055/s-0037-1611211

DO - 10.1055/s-0037-1611211

M3 - Article

AN - SCOPUS:85065177733

VL - 51

SP - 2230

EP - 2236

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 10

ER -

ID: 46259495