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Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts. / Filimonov, Victor D.; Krasnokutskaya, Elena A.; Kassanova, Assia Zh et al.

In: European Journal of Organic Chemistry, Vol. 2019, No. 4, 31.01.2019, p. 665-674.

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

Harvard

Filimonov, VD, Krasnokutskaya, EA, Kassanova, AZ, Fedorova, VA, Stankevich, KS, Naumov, NG, Bondarev, AA & Kataeva, VA 2019, 'Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts', European Journal of Organic Chemistry, vol. 2019, no. 4, pp. 665-674. https://doi.org/10.1002/ejoc.201800887

APA

Filimonov, V. D., Krasnokutskaya, E. A., Kassanova, A. Z., Fedorova, V. A., Stankevich, K. S., Naumov, N. G., Bondarev, A. A., & Kataeva, V. A. (2019). Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts. European Journal of Organic Chemistry, 2019(4), 665-674. https://doi.org/10.1002/ejoc.201800887

Vancouver

Filimonov VD, Krasnokutskaya EA, Kassanova AZ, Fedorova VA, Stankevich KS, Naumov NG et al. Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts. European Journal of Organic Chemistry. 2019 Jan 31;2019(4):665-674. doi: 10.1002/ejoc.201800887

Author

Filimonov, Victor D. ; Krasnokutskaya, Elena A. ; Kassanova, Assia Zh et al. / Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts. In: European Journal of Organic Chemistry. 2019 ; Vol. 2019, No. 4. pp. 665-674.

BibTeX

@article{3f18c4038f654cddbc9ab82ea6167fc6,
title = "Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts",
abstract = "Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2 + TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.",
keywords = "Aromatic substitution, Diazo compounds, Diazonium salts, Solvent effects, Synthetic methods, ARYL DIAZONIUM, PALLADIUM, O-BENZENEDISULFONIMIDES, IODINATION, IONS, AROMATIC-AMINES, DIAZOTIZATION, C-H ARYLATION, COUPLING REACTIONS, TOSYLATE SALTS",
author = "Filimonov, {Victor D.} and Krasnokutskaya, {Elena A.} and Kassanova, {Assia Zh} and Fedorova, {Valentina A.} and Stankevich, {Ksenia S.} and Naumov, {Nikolay G.} and Bondarev, {Alexander A.} and Kataeva, {Veronika A.}",
note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",
year = "2019",
month = jan,
day = "31",
doi = "10.1002/ejoc.201800887",
language = "English",
volume = "2019",
pages = "665--674",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "4",

}

RIS

TY - JOUR

T1 - Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts

AU - Filimonov, Victor D.

AU - Krasnokutskaya, Elena A.

AU - Kassanova, Assia Zh

AU - Fedorova, Valentina A.

AU - Stankevich, Ksenia S.

AU - Naumov, Nikolay G.

AU - Bondarev, Alexander A.

AU - Kataeva, Veronika A.

N1 - Publisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2019/1/31

Y1 - 2019/1/31

N2 - Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2 + TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.

AB - Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2 + TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.

KW - Aromatic substitution

KW - Diazo compounds

KW - Diazonium salts

KW - Solvent effects

KW - Synthetic methods

KW - ARYL DIAZONIUM

KW - PALLADIUM

KW - O-BENZENEDISULFONIMIDES

KW - IODINATION

KW - IONS

KW - AROMATIC-AMINES

KW - DIAZOTIZATION

KW - C-H ARYLATION

KW - COUPLING REACTIONS

KW - TOSYLATE SALTS

UR - http://www.scopus.com/inward/record.url?scp=85053045771&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201800887

DO - 10.1002/ejoc.201800887

M3 - Article

AN - SCOPUS:85053045771

VL - 2019

SP - 665

EP - 674

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 4

ER -

ID: 16483679