Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes

Standard

Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes. / Щербаков, Николай Викторович ; Дарьин, Дмитрий Викторович ; Кукушкин, Вадим Юрьевич ; Дубовцев, Алексей Юрьевич.

In: Journal of Organic Chemistry, Vol. 86, No. 18, 17.09.2021, p. 12964-12972.

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

BibTeX

@article{8e864667984d4d56a7e1682bdfb633ef,

title = "Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes",

abstract = "The gold-catalyzed reaction between benzofuroxans, functioning as nitrene transfer reagents, and N-allylynamides leads to 3-azabicyclo[3.1.0]hexan-2-imines. This highly selective annulation proceeds smoothly under mild conditions (5 mol % Ph3PAuNTf2, PhCl, 60 °C) and exhibits high functional group tolerance (21 examples, ≤96% yields). The obtained cyclopropanated products represent a useful synthetic platform with an easily modulated substitution pattern as illustrated by their postmodifications. Intramolecular cyclopropanation of gold α-imino carbene intermediates is suggested as a key step of the catalytic cycle.",

keywords = "2H-AZIRINES, ACCESS, ALKYNES, ANTHRANILS, CARBENES, COUNTER ANIONS, EFFICIENT, GENERATION, INDUSTRIAL PERSPECTIVE, YNAMIDES",

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

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

year = "2021",

month = sep,

day = "17",

doi = "10.1021/acs.joc.1c01654",

language = "English",

volume = "86",

pages = "12964--12972",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "18",

}

RIS

TY - JOUR

T1 - Gold-Catalyzed Nitrene Transfer from Benzofuroxans to N-Allylynamides: Synthesis of 3-Azabicyclo[3.1.0]hexanes

AU - Щербаков, Николай Викторович

AU - Дарьин, Дмитрий Викторович

AU - Кукушкин, Вадим Юрьевич

AU - Дубовцев, Алексей Юрьевич

PY - 2021/9/17

Y1 - 2021/9/17

N2 - The gold-catalyzed reaction between benzofuroxans, functioning as nitrene transfer reagents, and N-allylynamides leads to 3-azabicyclo[3.1.0]hexan-2-imines. This highly selective annulation proceeds smoothly under mild conditions (5 mol % Ph3PAuNTf2, PhCl, 60 °C) and exhibits high functional group tolerance (21 examples, ≤96% yields). The obtained cyclopropanated products represent a useful synthetic platform with an easily modulated substitution pattern as illustrated by their postmodifications. Intramolecular cyclopropanation of gold α-imino carbene intermediates is suggested as a key step of the catalytic cycle.

AB - The gold-catalyzed reaction between benzofuroxans, functioning as nitrene transfer reagents, and N-allylynamides leads to 3-azabicyclo[3.1.0]hexan-2-imines. This highly selective annulation proceeds smoothly under mild conditions (5 mol % Ph3PAuNTf2, PhCl, 60 °C) and exhibits high functional group tolerance (21 examples, ≤96% yields). The obtained cyclopropanated products represent a useful synthetic platform with an easily modulated substitution pattern as illustrated by their postmodifications. Intramolecular cyclopropanation of gold α-imino carbene intermediates is suggested as a key step of the catalytic cycle.

KW - 2H-AZIRINES

KW - ACCESS

KW - ALKYNES

KW - ANTHRANILS

KW - CARBENES

KW - COUNTER ANIONS

KW - EFFICIENT

KW - GENERATION

KW - INDUSTRIAL PERSPECTIVE

KW - YNAMIDES

UR - http://www.scopus.com/inward/record.url?scp=85114860454&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/edd5442b-3022-3425-a9ac-9bbaaaf26569/

U2 - 10.1021/acs.joc.1c01654

DO - 10.1021/acs.joc.1c01654

M3 - Article

VL - 86

SP - 12964

EP - 12972

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 18

ER -

ID: 87337614