Synthesis of 2-(2-Pyridyl)-2 H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines

Standard

Synthesis of 2-(2-Pyridyl)-2 H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines. / Agafonova, Anastasiya V.; Smetanin, Ilia A.; Rostovskii, Nikolai V.; Khlebnikov, Alexander F.; Novikov, Mikhail S.

In: Organic Letters, Vol. 23, No. 20, 15.10.2021, p. 8045-8049.

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

BibTeX

@article{cb3983824b364c6a909ddcf2d102e882,

title = "Synthesis of 2-(2-Pyridyl)-2 H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines",

abstract = "A high-yield method for the introduction of a 2-pyridyl substituent in the C2 position of the three-membered ring of 2-bromo-2H-azirine-2-carboxylic acid derivatives by the direct cross-coupling with 2-(trialkylstannyl)pyridines has been described. The reaction works well with 3-, 4-, or 5-substituted 2-stannylpyridines and can be also employed for the synthesis of 2-(thiazol-2-yl)-2H-azirines. According to DFT calculations, the reaction proceeds through the sequence of SN2′-substitution of bromine, 1,4-stannyl shift, and [2,3]-sigmatropic shift of the pyridine ring. ",

keywords = "RING CONTRACTION, 2H-AZIRINES, ACCESS, REACTIVITY, EFFICIENT",

author = "Agafonova, {Anastasiya V.} and Smetanin, {Ilia A.} and Rostovskii, {Nikolai V.} and Khlebnikov, {Alexander F.} and Novikov, {Mikhail S.}",

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

year = "2021",

month = oct,

day = "15",

doi = "10.1021/acs.orglett.1c03060",

language = "English",

volume = "23",

pages = "8045--8049",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "20",

}

RIS

TY - JOUR

T1 - Synthesis of 2-(2-Pyridyl)-2 H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines

AU - Agafonova, Anastasiya V.

AU - Smetanin, Ilia A.

AU - Rostovskii, Nikolai V.

AU - Khlebnikov, Alexander F.

AU - Novikov, Mikhail S.

PY - 2021/10/15

Y1 - 2021/10/15

N2 - A high-yield method for the introduction of a 2-pyridyl substituent in the C2 position of the three-membered ring of 2-bromo-2H-azirine-2-carboxylic acid derivatives by the direct cross-coupling with 2-(trialkylstannyl)pyridines has been described. The reaction works well with 3-, 4-, or 5-substituted 2-stannylpyridines and can be also employed for the synthesis of 2-(thiazol-2-yl)-2H-azirines. According to DFT calculations, the reaction proceeds through the sequence of SN2′-substitution of bromine, 1,4-stannyl shift, and [2,3]-sigmatropic shift of the pyridine ring.

AB - A high-yield method for the introduction of a 2-pyridyl substituent in the C2 position of the three-membered ring of 2-bromo-2H-azirine-2-carboxylic acid derivatives by the direct cross-coupling with 2-(trialkylstannyl)pyridines has been described. The reaction works well with 3-, 4-, or 5-substituted 2-stannylpyridines and can be also employed for the synthesis of 2-(thiazol-2-yl)-2H-azirines. According to DFT calculations, the reaction proceeds through the sequence of SN2′-substitution of bromine, 1,4-stannyl shift, and [2,3]-sigmatropic shift of the pyridine ring.

KW - RING CONTRACTION

KW - 2H-AZIRINES

KW - ACCESS

KW - REACTIVITY

KW - EFFICIENT

UR - http://www.scopus.com/inward/record.url?scp=85117130574&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/9adebd7c-c0ce-3807-a099-4200c9c52554/

U2 - 10.1021/acs.orglett.1c03060

DO - 10.1021/acs.orglett.1c03060

M3 - Article

AN - SCOPUS:85117130574

VL - 23

SP - 8045

EP - 8049

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 20

ER -

ID: 87946712