TY  - JOUR
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban D.
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4358
AB  - The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines
VL  - 86
IS  - 6
SP  - 4794
EP  - 4803
DO  - 10.1021/acs.joc.1c00282
ER  - 

@article{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban D. and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
abstract = "The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines",
volume = "86",
number = "6",
pages = "4794-4803",
doi = "10.1021/acs.joc.1c00282"
}

Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B. D., Selaković, Ž., Ajdačić, V.,& Opsenica, I.. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry
American Chemical Society (ACS)., 86(6), 4794-4803.
https://doi.org/10.1021/acs.joc.1c00282

Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković BD, Selaković Ž, Ajdačić V, Opsenica I. Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry. 2021;86(6):4794-4803.
doi:10.1021/acs.joc.1c00282 .

Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban D., Selaković, Života, Ajdačić, Vladimir, Opsenica, Igor, "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines" in The Journal of Organic Chemistry, 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 . .

TY  - JOUR
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban D.
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4359
AB  - The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines
VL  - 86
IS  - 6
SP  - 4794
EP  - 4803
DO  - 10.1021/acs.joc.1c00282
ER  - 

@article{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban D. and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
abstract = "The Pd-catalyzed N-arylation method for the synthesis of eighteen N,1-diaryl-1H-tetrazol-5-amine derivatives is reported. By running the reactions at 35 °C, compounds were isolated as single isomers since the undesired Dimroth rearrangement was completely suppressed. Furthermore, the Dimroth rearrangement of N,1-diaryl-1H-tetrazol-5-amines was rationalized by conducting comprehensive experiments and NMR analysis as well as density functional theory (DFT) calculations of thermodynamic stability of the compounds. It was established that the Dimroth rearrangement is thermodynamically controlled, and the equilibrium of the reaction is determined by the stability of the corresponding isomers. The mechanism was investigated by additional DFT calculations, and the opening of the tetrazole ring was shown to be the rate-determining step. By maneuvering Pd-catalyzed N-arylation and the subsequent Dimroth rearrangement, two more N,1-diaryl-1H-tetrazol-5-amine derivatives were acquired, which otherwise cannot be synthesized by employing the C–N cross-coupling reaction.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines",
volume = "86",
number = "6",
pages = "4794-4803",
doi = "10.1021/acs.joc.1c00282"
}

Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B. D., Selaković, Ž., Ajdačić, V.,& Opsenica, I.. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry
American Chemical Society (ACS)., 86(6), 4794-4803.
https://doi.org/10.1021/acs.joc.1c00282

Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković BD, Selaković Ž, Ajdačić V, Opsenica I. Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. in The Journal of Organic Chemistry. 2021;86(6):4794-4803.
doi:10.1021/acs.joc.1c00282 .

Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban D., Selaković, Života, Ajdačić, Vladimir, Opsenica, Igor, "Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines" in The Journal of Organic Chemistry, 86, no. 6 (2021):4794-4803,
https://doi.org/10.1021/acs.joc.1c00282 . .

TY  - DATA
AU  - Nikolić, Andrea
AU  - Stanić, Jelena
AU  - Zlatar, Matija
AU  - Gruden, Maja
AU  - Anđelković, Boban D.
AU  - Selaković, Života
AU  - Ajdačić, Vladimir
AU  - Opsenica, Igor
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4360
AB  - Copies of 1H and 13C NMR spectra for the synthesized compounds; Extended computational results, and total electronic energies, number of imaginary frequencies;  Cartesian coordinates of all structures.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - Supporting information for the article: Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry, American Chemical Society (ACS)., 86(6), 4794-4803. https://doi.org/10.1021/acs.joc.1c00282
DO  - 10.1021/acs.joc.1c00282.s001
ER  - 

@misc{
author = "Nikolić, Andrea and Stanić, Jelena and Zlatar, Matija and Gruden, Maja and Anđelković, Boban D. and Selaković, Života and Ajdačić, Vladimir and Opsenica, Igor",
year = "2021",
abstract = "Copies of 1H and 13C NMR spectra for the synthesized compounds; Extended computational results, and total electronic energies, number of imaginary frequencies;  Cartesian coordinates of all structures.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "Supporting information for the article: Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry, American Chemical Society (ACS)., 86(6), 4794-4803. https://doi.org/10.1021/acs.joc.1c00282",
doi = "10.1021/acs.joc.1c00282.s001"
}

Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B. D., Selaković, Ž., Ajdačić, V.,& Opsenica, I.. (2021). Supporting information for the article: Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry, American Chemical Society (ACS)., 86(6), 4794-4803. https://doi.org/10.1021/acs.joc.1c00282. in The Journal of Organic Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.joc.1c00282.s001

Nikolić A, Stanić J, Zlatar M, Gruden M, Anđelković BD, Selaković Ž, Ajdačić V, Opsenica I. Supporting information for the article: Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry, American Chemical Society (ACS)., 86(6), 4794-4803. https://doi.org/10.1021/acs.joc.1c00282. in The Journal of Organic Chemistry. 2021;.
doi:10.1021/acs.joc.1c00282.s001 .

Nikolić, Andrea, Stanić, Jelena, Zlatar, Matija, Gruden, Maja, Anđelković, Boban D., Selaković, Života, Ajdačić, Vladimir, Opsenica, Igor, "Supporting information for the article: Nikolić, A., Stanić, J., Zlatar, M., Gruden, M., Anđelković, B., Selaković, Ž., Ajdačić, V.,& Opsenica, I. (2021). Controlling Pd-Catalyzed N-Arylation and Dimroth Rearrangement in the Synthesis of N,1-Diaryl-1H-tetrazol-5-amines. The Journal of Organic Chemistry, American Chemical Society (ACS)., 86(6), 4794-4803. https://doi.org/10.1021/acs.joc.1c00282" in The Journal of Organic Chemistry (2021),
https://doi.org/10.1021/acs.joc.1c00282.s001 . .