Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Synthesis, Structure, and Synthetic Potential of Arenediazonium Trifluoromethanesulfonates as Stable and Safe Diazonium Salts. / Filimonov, Victor D.; Krasnokutskaya, Elena A.; Kassanova, Assia Zh и др.
в: European Journal of Organic Chemistry, Том 2019, № 4, 31.01.2019, стр. 665-674.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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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