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Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts. / Солдатова, Наталья Сергеевна; Семёнов, Артём; Гейль, Кирилл Константинович; Байков, Сергей Валентинович; Шетнев, Антон; Константинова, Анна; Корсаков, Михаил Константинович; Юсубов, М.С.; Постников, П.С.

In: Advanced Synthesis and Catalysis, Vol. 363, No. 14, 20.07.2021, p. 3566-3576.

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

Harvard

Солдатова, НС, Семёнов, А, Гейль, КК, Байков, СВ, Шетнев, А, Константинова, А, Корсаков, МК, Юсубов, МС & Постников, ПС 2021, 'Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts', Advanced Synthesis and Catalysis, vol. 363, no. 14, pp. 3566-3576. https://doi.org/10.1002/adsc.202100426

APA

Солдатова, Н. С., Семёнов, А., Гейль, К. К., Байков, С. В., Шетнев, А., Константинова, А., Корсаков, М. К., Юсубов, М. С., & Постников, П. С. (2021). Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts. Advanced Synthesis and Catalysis, 363(14), 3566-3576. https://doi.org/10.1002/adsc.202100426

Vancouver

Солдатова НС, Семёнов А, Гейль КК, Байков СВ, Шетнев А, Константинова А et al. Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts. Advanced Synthesis and Catalysis. 2021 Jul 20;363(14):3566-3576. https://doi.org/10.1002/adsc.202100426

Author

Солдатова, Наталья Сергеевна ; Семёнов, Артём ; Гейль, Кирилл Константинович ; Байков, Сергей Валентинович ; Шетнев, Антон ; Константинова, Анна ; Корсаков, Михаил Константинович ; Юсубов, М.С. ; Постников, П.С. / Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts. In: Advanced Synthesis and Catalysis. 2021 ; Vol. 363, No. 14. pp. 3566-3576.

BibTeX

@article{6a213f2f276940f88d8f9770f9a68ab4,
title = "Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts",
abstract = "Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol. (Figure presented.).",
keywords = "Amides, Arylation, Chemoselectivity, Heterocycles, Iodonium salts, ANTAGONIST, 2-PYRIDONES, ONE-POT SYNTHESIS, ARENES, IODINE, ALKYNYLATION, ANILINES, ARYL IODIDES, EFFICIENT, CYCLIZATION",
author = "Солдатова, {Наталья Сергеевна} and Артём Семёнов and Гейль, {Кирилл Константинович} and Байков, {Сергей Валентинович} and Антон Шетнев and Анна Константинова and Корсаков, {Михаил Константинович} and М.С. Юсубов and П.С. Постников",
note = "Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",
year = "2021",
month = jul,
day = "20",
doi = "10.1002/adsc.202100426",
language = "English",
volume = "363",
pages = "3566--3576",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-Blackwell",
number = "14",

}

RIS

TY - JOUR

T1 - Copper-Catalyzed Selective N-Arylation of Oxadiazolones by Diaryliodonium Salts

AU - Солдатова, Наталья Сергеевна

AU - Семёнов, Артём

AU - Гейль, Кирилл Константинович

AU - Байков, Сергей Валентинович

AU - Шетнев, Антон

AU - Константинова, Анна

AU - Корсаков, Михаил Константинович

AU - Юсубов, М.С.

AU - Постников, П.С.

N1 - Publisher Copyright: © 2021 Wiley-VCH GmbH

PY - 2021/7/20

Y1 - 2021/7/20

N2 - Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol. (Figure presented.).

AB - Here, we report the method for copper-catalyzed N-arylation of diverse oxadiazolones by diaryliodonium salts under mild conditions in high yields (up to 92%) using available CuI as a catalyst. The developed method allows utilizing both symmetric and unsymmetric diaryliodonium salts bearing auxiliary groups such as 2,4,6-trimethoxyphenyl (TMP). We found that the steric effects in aryl moieties determined the chemoselectivity of N- and O-arylation of the 1,2,4-oxadiazol-5(4H)-ones. Mesityl-substituted diaryliodonium salts demonstrated the high potential as a selective arylation reagent. The structural study suggests that steric accessibility of N-atom in 1,2,4-oxadiazol-5(4H)-ones impact to arylation with sterically hindered diaryliodonium salts. The synthetic application of proposed method was also demonstrated on selective arylation of 1,3,4-oxadiazol-2(3H)-ones and 1,2,4-oxadiazole-5-thiol. (Figure presented.).

KW - Amides

KW - Arylation

KW - Chemoselectivity

KW - Heterocycles

KW - Iodonium salts

KW - ANTAGONIST

KW - 2-PYRIDONES

KW - ONE-POT SYNTHESIS

KW - ARENES

KW - IODINE

KW - ALKYNYLATION

KW - ANILINES

KW - ARYL IODIDES

KW - EFFICIENT

KW - CYCLIZATION

UR - http://www.scopus.com/inward/record.url?scp=85107761429&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/425d9b73-165b-3d27-b109-2d7fd7e3f7f1/

U2 - 10.1002/adsc.202100426

DO - 10.1002/adsc.202100426

M3 - Article

VL - 363

SP - 3566

EP - 3576

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 14

ER -

ID: 83137416