Standard

Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of α-aminoketones and electron-deficient alkynes as a route to 3-EWG-substituted pyrrole. / Чикунова, Елена Игоревна; Котикова, Полина Филипповна; Дарьин, Дмитрий Викторович; Кукушкин, Вадим Юрьевич; Дубовцев, Алексей Юрьевич.

In: Catalysis Science and Technology, 01.08.2024.

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

Harvard

Чикунова, ЕИ, Котикова, ПФ, Дарьин, ДВ, Кукушкин, ВЮ & Дубовцев, АЮ 2024, 'Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of α-aminoketones and electron-deficient alkynes as a route to 3-EWG-substituted pyrrole', Catalysis Science and Technology. https://doi.org/10.1039/D4CY00660G

APA

Чикунова, Е. И., Котикова, П. Ф., Дарьин, Д. В., Кукушкин, В. Ю., & Дубовцев, А. Ю. (2024). Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of α-aminoketones and electron-deficient alkynes as a route to 3-EWG-substituted pyrrole. Catalysis Science and Technology. https://doi.org/10.1039/D4CY00660G

Vancouver

Чикунова ЕИ, Котикова ПФ, Дарьин ДВ, Кукушкин ВЮ, Дубовцев АЮ. Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of α-aminoketones and electron-deficient alkynes as a route to 3-EWG-substituted pyrrole. Catalysis Science and Technology. 2024 Aug 1. https://doi.org/10.1039/D4CY00660G

Author

Чикунова, Елена Игоревна ; Котикова, Полина Филипповна ; Дарьин, Дмитрий Викторович ; Кукушкин, Вадим Юрьевич ; Дубовцев, Алексей Юрьевич. / Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of α-aminoketones and electron-deficient alkynes as a route to 3-EWG-substituted pyrrole. In: Catalysis Science and Technology. 2024.

BibTeX

@article{a487734086c44540aab5b3d0ff8b1089,
title = "Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of α-aminoketones and electron-deficient alkynes as a route to 3-EWG-substituted pyrrole",
abstract = "Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of α-aminoketones and electron-deficient alkynes provides a modular one-step route to a variety of 3-EWG-substituted pyrroles. Apart from gold(i) complexes, which “open any door” and catalyze the annulation regardless of the identity of the alkyne EWGs [-SO2R, -CO2R, -PO(OR)2], the other cheaper coinage metal (first of all Cu, but also Ag) species function as alternative catalysts for the selective activation of alkynylsulfones and their conversion to 3-sulfonylpyrroles. The developed catalytic annulation operates under relatively mild conditions (5 mol% of a coinage metal catalyst, DCE, 80 °C) and provides a high functional group tolerance (36 examples; yields up to 99%). The synthetic utility of the obtained products was illustrated by practical post-modification of either the pyrrole backbone, or the peripheral substituents.",
author = "Чикунова, {Елена Игоревна} and Котикова, {Полина Филипповна} and Дарьин, {Дмитрий Викторович} and Кукушкин, {Вадим Юрьевич} and Дубовцев, {Алексей Юрьевич}",
year = "2024",
month = aug,
day = "1",
doi = "10.1039/D4CY00660G",
language = "English",
journal = "Catalysis Science and Technology",
issn = "2044-4753",
publisher = "Royal Society of Chemistry",

}

RIS

TY - JOUR

T1 - Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of α-aminoketones and electron-deficient alkynes as a route to 3-EWG-substituted pyrrole

AU - Чикунова, Елена Игоревна

AU - Котикова, Полина Филипповна

AU - Дарьин, Дмитрий Викторович

AU - Кукушкин, Вадим Юрьевич

AU - Дубовцев, Алексей Юрьевич

PY - 2024/8/1

Y1 - 2024/8/1

N2 - Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of α-aminoketones and electron-deficient alkynes provides a modular one-step route to a variety of 3-EWG-substituted pyrroles. Apart from gold(i) complexes, which “open any door” and catalyze the annulation regardless of the identity of the alkyne EWGs [-SO2R, -CO2R, -PO(OR)2], the other cheaper coinage metal (first of all Cu, but also Ag) species function as alternative catalysts for the selective activation of alkynylsulfones and their conversion to 3-sulfonylpyrroles. The developed catalytic annulation operates under relatively mild conditions (5 mol% of a coinage metal catalyst, DCE, 80 °C) and provides a high functional group tolerance (36 examples; yields up to 99%). The synthetic utility of the obtained products was illustrated by practical post-modification of either the pyrrole backbone, or the peripheral substituents.

AB - Coinage (Au, Ag, Cu) metal-catalyzed (3 + 2) annulation of α-aminoketones and electron-deficient alkynes provides a modular one-step route to a variety of 3-EWG-substituted pyrroles. Apart from gold(i) complexes, which “open any door” and catalyze the annulation regardless of the identity of the alkyne EWGs [-SO2R, -CO2R, -PO(OR)2], the other cheaper coinage metal (first of all Cu, but also Ag) species function as alternative catalysts for the selective activation of alkynylsulfones and their conversion to 3-sulfonylpyrroles. The developed catalytic annulation operates under relatively mild conditions (5 mol% of a coinage metal catalyst, DCE, 80 °C) and provides a high functional group tolerance (36 examples; yields up to 99%). The synthetic utility of the obtained products was illustrated by practical post-modification of either the pyrrole backbone, or the peripheral substituents.

UR - https://www.mendeley.com/catalogue/3cae11c0-ed9b-3b5f-89f9-c701fb4a66da/

U2 - 10.1039/D4CY00660G

DO - 10.1039/D4CY00660G

M3 - Article

JO - Catalysis Science and Technology

JF - Catalysis Science and Technology

SN - 2044-4753

ER -

ID: 123878204