Redox-Neutral and Atom-Economic Route to β‑Carbolines via Gold- Catalyzed [4 + 2] Cycloaddition of Indolylynamides and Cyanamides

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Redox-Neutral and Atom-Economic Route to β‑Carbolines via Gold- Catalyzed [4 + 2] Cycloaddition of Indolylynamides and Cyanamides. / Щербаков, Николай Викторович ; Чикунова, Елена Игоревна ; Дарьин, Дмитрий Викторович ; Кукушкин, Вадим Юрьевич ; Дубовцев, Алексей Юрьевич.

In: Journal of Organic Chemistry, Vol. 86, No. 24, 23.11.2021, p. 17804 - 17815.

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

BibTeX

@article{e2d4d18e9aa04bf09d828aed64f77e18,

title = "Redox-Neutral and Atom-Economic Route to β‑Carbolines via Gold- Catalyzed [4 + 2] Cycloaddition of Indolylynamides and Cyanamides",

abstract = "Gold(I)-catalyzed [4 + 2] cycloaddition of indolylynamides and cyanamides (aminonitriles) is an efficient redox-neutral and atom-economic route to diversely substituted 1,3-diamino-β-carbolines. The protocol operates under mild conditions (Ph3PAuNTf2 5 mol %, DCE, 60 °C) with a good tolerance to functional groups (23 examples and yields up to 98%). The obtained β-carboline systems represent a versatile synthetic platform with modifiable substituents for successive functionalizations. Control experiments indicate the crucial role of both the nature of reactants and the identity of employed catalysts in the developed cycloaddition.",

author = "Щербаков, {Николай Викторович} and Чикунова, {Елена Игоревна} and Дарьин, {Дмитрий Викторович} and Кукушкин, {Вадим Юрьевич} and Дубовцев, {Алексей Юрьевич}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = nov,

day = "23",

doi = "10.1021/acs.joc.1c02119",

language = "English",

volume = "86",

pages = "17804 -- 17815",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "24",

}

RIS

TY - JOUR

T1 - Redox-Neutral and Atom-Economic Route to β‑Carbolines via Gold- Catalyzed [4 + 2] Cycloaddition of Indolylynamides and Cyanamides

AU - Щербаков, Николай Викторович

AU - Чикунова, Елена Игоревна

AU - Дарьин, Дмитрий Викторович

AU - Кукушкин, Вадим Юрьевич

AU - Дубовцев, Алексей Юрьевич

PY - 2021/11/23

Y1 - 2021/11/23

N2 - Gold(I)-catalyzed [4 + 2] cycloaddition of indolylynamides and cyanamides (aminonitriles) is an efficient redox-neutral and atom-economic route to diversely substituted 1,3-diamino-β-carbolines. The protocol operates under mild conditions (Ph3PAuNTf2 5 mol %, DCE, 60 °C) with a good tolerance to functional groups (23 examples and yields up to 98%). The obtained β-carboline systems represent a versatile synthetic platform with modifiable substituents for successive functionalizations. Control experiments indicate the crucial role of both the nature of reactants and the identity of employed catalysts in the developed cycloaddition.

AB - Gold(I)-catalyzed [4 + 2] cycloaddition of indolylynamides and cyanamides (aminonitriles) is an efficient redox-neutral and atom-economic route to diversely substituted 1,3-diamino-β-carbolines. The protocol operates under mild conditions (Ph3PAuNTf2 5 mol %, DCE, 60 °C) with a good tolerance to functional groups (23 examples and yields up to 98%). The obtained β-carboline systems represent a versatile synthetic platform with modifiable substituents for successive functionalizations. Control experiments indicate the crucial role of both the nature of reactants and the identity of employed catalysts in the developed cycloaddition.

UR - http://www.scopus.com/inward/record.url?scp=85120377311&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/3536c367-3689-3878-a196-cc0012e1b899/

U2 - 10.1021/acs.joc.1c02119

DO - 10.1021/acs.joc.1c02119

M3 - Article

VL - 86

SP - 17804

EP - 17815

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 24

ER -

ID: 88773580