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Regioselectivity of the Chan–Lam coupling of ambident nitropyrazoles with trans-styrylboronic acid

Dmitry Vladimirovich Davydov 1
Dmitry Vladimirovich Davydov
, 
Petr Kirillovich Sazonov 1
Petr Kirillovich Sazonov
, 
Yurii Fedorovich Oprunenko 1
Yurii Fedorovich Oprunenko
10.1016/j.mencom.2020.03.018
Published 2020-03-02
Communication , Volume 30, Issue 2, 185-187
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Davydov D. V., Sazonov P. K., Oprunenko Y. F. Regioselectivity of the Chan–Lam coupling of ambident nitropyrazoles with trans-styrylboronic acid // Mendeleev Communications. 2020. Vol. 30. No. 2. pp. 185-187.
GOST all authors (up to 50) Copy
Davydov D. V., Sazonov P. K., Oprunenko Y. F. Regioselectivity of the Chan–Lam coupling of ambident nitropyrazoles with trans-styrylboronic acid // Mendeleev Communications. 2020. Vol. 30. No. 2. pp. 185-187.
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TY - JOUR
DO - 10.1016/j.mencom.2020.03.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.018
TI - Regioselectivity of the Chan–Lam coupling of ambident nitropyrazoles with trans-styrylboronic acid
T2 - Mendeleev Communications
AU - Davydov, Dmitry Vladimirovich
AU - Sazonov, Petr Kirillovich
AU - Oprunenko, Yurii Fedorovich
PY - 2020
DA - 2020/03/02
PB - Mendeleev Communications
SP - 185-187
IS - 2
VL - 30
ER -
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@article{2020_Davydov,
author = {Dmitry Vladimirovich Davydov and Petr Kirillovich Sazonov and Yurii Fedorovich Oprunenko},
title = {Regioselectivity of the Chan–Lam coupling of ambident nitropyrazoles with trans-styrylboronic acid},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.018},
number = {2},
pages = {185--187},
doi = {10.1016/j.mencom.2020.03.018}
}
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Davydov, Dmitry Vladimirovich, et al. “Regioselectivity of the Chan–Lam coupling of ambident nitropyrazoles with trans-styrylboronic acid.” Mendeleev Communications, vol. 30, no. 2, Mar. 2020, pp. 185-187. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.018.

Keywords

13C NMR
Chan–Lam reaction
copper catalysis
DFT
nitropyrazoles
pyrazoles
vinylboronic acids
vinylpyrazoles

Abstract

Regioselectivity of the Chan–Lam coupling of ambident nitropyrazoles with trans-styrylboronic acid depends on the base and catalyst nature and can vary the N(1)/N(2)-isomer ratio from ∼2 : 1 to ∼1 : 2. 2-Methyl-4-nitro- and 2,4-dinitroimidazoles are unreactive in this reaction. The structure of N(1)/N(2) isomers was elucidated by NOE measurements and by the comparison of experimental and DFT calculated 13C NMR chemical shifts.

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