Home / Publications / Ruthenium(II)-catalyzed C(3)–H arylation of furan moiety in fuberidazole derivatives

Ruthenium(II)-catalyzed C(3)–H arylation of furan moiety in fuberidazole derivatives

Konstantin Evgen'evich Shepelenko 1
Konstantin Evgen'evich Shepelenko
Ksenia Alekseevna Nikolaeva 1
Ksenia Alekseevna Nikolaeva
Irina Gennad'evna Gnatiuk 1
Irina Gennad'evna Gnatiuk
Olga Gennad'evna Garanzha 1
Olga Gennad'evna Garanzha
Andrey Anatol'evich Alexandrov 1
Andrey Anatol'evich Alexandrov
Viktor Mikhailovich Chernyshev 1
Viktor Mikhailovich Chernyshev
Published 2022-07-01
CommunicationVolume 32, Issue 4, 485-487
8
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Shepelenko K. E. et al. Ruthenium(II)-catalyzed C(3)–H arylation of furan moiety in fuberidazole derivatives // Mendeleev Communications. 2022. Vol. 32. No. 4. pp. 485-487.
GOST all authors (up to 50) Copy
Shepelenko K. E., Nikolaeva K. A., Gnatiuk I. G., Garanzha O. G., Alexandrov A. A., Minyaev M. E., Chernyshev V. M. Ruthenium(II)-catalyzed C(3)–H arylation of furan moiety in fuberidazole derivatives // Mendeleev Communications. 2022. Vol. 32. No. 4. pp. 485-487.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2022.07.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.018
TI - Ruthenium(II)-catalyzed C(3)–H arylation of furan moiety in fuberidazole derivatives
T2 - Mendeleev Communications
AU - Shepelenko, Konstantin Evgen'evich
AU - Nikolaeva, Ksenia Alekseevna
AU - Gnatiuk, Irina Gennad'evna
AU - Garanzha, Olga Gennad'evna
AU - Alexandrov, Andrey Anatol'evich
AU - Minyaev, Mikhail Evgenievich
AU - Chernyshev, Viktor Mikhailovich
PY - 2022
DA - 2022/07/01
PB - Mendeleev Communications
SP - 485-487
IS - 4
VL - 32
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2022_Shepelenko,
author = {Konstantin Evgen'evich Shepelenko and Ksenia Alekseevna Nikolaeva and Irina Gennad'evna Gnatiuk and Olga Gennad'evna Garanzha and Andrey Anatol'evich Alexandrov and Mikhail Evgenievich Minyaev and Viktor Mikhailovich Chernyshev},
title = {Ruthenium(II)-catalyzed C(3)–H arylation of furan moiety in fuberidazole derivatives},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.018},
number = {4},
pages = {485--487},
doi = {10.1016/j.mencom.2022.07.018}
}
MLA
Cite this
MLA Copy
Shepelenko, Konstantin Evgen'evich, et al. “Ruthenium(II)-catalyzed C(3)–H arylation of furan moiety in fuberidazole derivatives.” Mendeleev Communications, vol. 32, no. 4, Jul. 2022, pp. 485-487. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.018.

Keywords

2-hetarylfurans
arylation
benzimidazoles
carboxylate assistance
CH-functionalization
furans
ruthenium complexes

Abstract

An efficient selective C(3)–H arylation of furan ring in 2-(furan-2-yl)benzimidazoles, derivatives of fuberidazole fungicide, with aryl bromides catalyzed by [RuCl2(cymene)]2/ pivalic acid system has been accomplished. High selectivity of the process may be accounted for by the action of benzimidazol-2-yl substituent as the directing group.

References

1.
Atom-economic approach to the synthesis of α-(hetero)aryl substituted furan derivatives from biomass.
Romashov L.V., Kozlov K.S., Skorobogatko M.K., Kostyukovich A.Y., Ananikov V.P.
Chemistry - An Asian Journal, 2021
2.
10.1016/j.mencom.2022.07.018_b0010
Banerjee
Int. J. Rev. Life Sci., 2012
3.
Verbitskiy E.V., Baskakova S.A., Belyaev D.V., Vakhrusheva D.V., Eremeeva N.I., Rusinov G.L., Charushin V.N.
Mendeleev Communications, 2021
4.
The efficacy of lapatinib and capecitabine in HER-2 positive breast cancer with brain metastases: A systematic review and pooled analysis
Petrelli F., Ghidini M., Lonati V., Tomasello G., Borgonovo K., Ghilardi M., Cabiddu M., Barni S.
European Journal of Cancer, 2017
7.
10.1016/j.mencom.2022.07.018_b0035
Aftab
Int. J. Environ. Anal. Chem., 2021
9.
Part I. Synthesis, biological evaluation and docking studies of new 2-furylbenzimidazoles as antiangiogenic agents
Temirak A., Shaker Y.M., Ragab F.A., Ali M.M., Ali H.I., El Diwani H.I.
European Journal of Medicinal Chemistry, 2014
10.
Design, synthesis, molecular docking and cytotoxic evaluation of novel 2-furybenzimidazoles as VEGFR-2 inhibitors
Abdullaziz M.A., Abdel-Mohsen H.T., El Kerdawy A.M., Ragab F.A., Ali M.M., Abu-bakr S.M., Girgis A.S., El Diwani H.I.
European Journal of Medicinal Chemistry, 2017
11.
Targeting Receptor Tyrosine Kinase VEGFR-2 in Hepatocellular Cancer: Rational Design, Synthesis and Biological Evaluation of 1,2-Disubstituted Benzimidazoles
Abdel-Mohsen H.T., Abdullaziz M.A., El Kerdawy A.M., Ragab F.A., Flanagan K.J., Mahmoud A.E., Ali M.M., El Diwani H.I., Senge M.O.
Molecules, 2020
12.
Biological Activity of Newly Synthesized Benzimidazole and Benzothizole 2,5-Disubstituted Furane Derivatives
Racané L., Zlatar I., Perin N., Cindrić M., Radovanović V., Banjanac M., Shanmugam S., Stojković M.R., Brajša K., Hranjec M.
Molecules, 2021
13.
Direct inhibition of the DNA-binding activity of POU transcription factors Pit-1 and Brn-3 by selective binding of a phenyl-furan-benzimidazole dication
Peixoto P., Liu Y., Depauw S., Hildebrand M., Boykin D.W., Bailly C., Wilson W.D., David-Cordonnier M.
Nucleic Acids Research, 2008
18.
Synthesis and Reactivity of 2-(Furan-2-yl)benzo[1,2-d:4,3-d′]bis[1,3]thiazole
Aleksandrov A.A., Elchaninov M.M., Tishina D.A., Tarakanova Y.E., Shmanovsky M.L.
Russian Journal of Organic Chemistry, 2021
19.
2-(Fur-2-yl)thiazolo[4,5-f]quinoline: Synthesis and Electrophilic Substitution Reactions
Aleksandrov A.A., El’chaninov M.M., Zablotskii D.A.
Russian Journal of General Chemistry, 2019
20.
M. M. El’chaninov, A. M. Simonov and L. Ya. Oleinikova, Chem. Heterocycl. Compd., 1983, 19, 1041 (Khim. Geterotsikl. Soedin., 1983, 19, 1311).
22.
Ni/NHC catalysis in C–H functionalization using air-tolerant nickelocene and sodium formate for in situ catalyst generation
Khazipov O.V., Shepelenko K.E., Pasyukov D.V., Chesnokov V.V., Soliev S.B., Chernyshev V.M., Ananikov V.P.
Organic Chemistry Frontiers, 2021
23.
Regioselective Ru(II)/Pd(0) Dual Catalysis: One-Pot C–H Diarylation of Five-Membered Heterocyclic Derivatives
Al Mamari H.H., Grošelj U., Požgan F., Brodnik H.
Journal of Organic Chemistry, 2021
26.
Directing-Group-Free, Carbonyl Group-Promoted Catalytic C-H Arylation of Bio-Based Furans
Karlinskii B.Y., Kostyukovich A.Y., Kucherov F.A., Galkin K.I., Kozlov K.S., Ananikov V.P.
ACS Catalysis, 2020
29.
10.1016/j.mencom.2022.07.018_b0145
Siopa
Eur. J. Org. Chem., 2018
31.
Creating Diversity from Biomass: A Tandem Bio/Metal-Catalysis towards Chemoselective Synthesis of Densely Substituted Furans.
Ravasco J.M., Monteiro C.M., Siopa F., Trindade A.F., Oble J., Poli G., Simeonov S.P., Afonso C.A.
ChemSusChem, 2019
32.
10.1016/j.mencom.2022.07.018_b0160
Li
Synlett, 2017
33.
Ruthenium-catalyzed direct arylations with aryl chlorides
Zha G., Qin H., Kantchev E.A.
RSC Advances, 2016
35.
Shepelenko K.E., Nikolaeva K.A., Shevchenko M.A., Tkachenko Y.N., Minyaev M.E., Chernyshev V.M.
Mendeleev Communications, 2022