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.
| Original language | English |
|---|---|
| Pages (from-to) | 665-674 |
| Number of pages | 10 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2019 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 1 Jan 2019 |
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Keywords
- Aromatic substitution
- Diazo compounds
- Diazonium salts
- Solvent effects
- Synthetic methods
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts. / Filimonov, Victor D.; Krasnokutskaya, Elena A.; Kassanova, Assia Zh; Fedorova, Valentina A.; Stankevich, Ksenia S.; Naumov, Nikolay G.; Bondarev, Alexander A.; Kataeva, Veronika A.
In: European Journal of Organic Chemistry, Vol. 2019, No. 4, 01.01.2019, p. 665-674.Research output: Contribution to journal › Article
}
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.
PY - 2019/1/1
Y1 - 2019/1/1
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
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UR - http://www.scopus.com/inward/citedby.url?scp=85053045771&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201800887
DO - 10.1002/ejoc.201800887
M3 - Article
VL - 2019
SP - 665
EP - 674
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 4
ER -