Home / Publications / CF3-Carbenoid functionalization of N-(pyrimidin-2-yl)indole catalyzed by cobalt complexes: Ligand control of selectivity

CF3-Carbenoid functionalization of N-(pyrimidin-2-yl)indole catalyzed by cobalt complexes: Ligand control of selectivity

Sofya Sergeevna Kuvshinova 1
Sofya Sergeevna Kuvshinova
Alexander Fedorovich Smol'yakov 1, 2
Alexander Fedorovich Smol'yakov
Daria Vladimirovna Vorobyeva 1
Daria Vladimirovna Vorobyeva
Sergey Nikolaevich Osipov 1
Sergey Nikolaevich Osipov
Dmitry Alexandrovich Loginov 1
Dmitry Alexandrovich Loginov
Published 2018-06-29
CommunicationVolume 28, Issue 4, 359-361
13
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Kuvshinova S. S. et al. CF3-Carbenoid functionalization of N-(pyrimidin-2-yl)indole catalyzed by cobalt complexes: Ligand control of selectivity // Mendeleev Communications. 2018. Vol. 28. No. 4. pp. 359-361.
GOST all authors (up to 50) Copy
Kuvshinova S. S., Smol'yakov A. F., Vorobyeva D. V., Osipov S. N., Loginov D. A. CF3-Carbenoid functionalization of N-(pyrimidin-2-yl)indole catalyzed by cobalt complexes: Ligand control of selectivity // Mendeleev Communications. 2018. Vol. 28. No. 4. pp. 359-361.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2018.07.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.07.005
TI - CF3-Carbenoid functionalization of N-(pyrimidin-2-yl)indole catalyzed by cobalt complexes: Ligand control of selectivity
T2 - Mendeleev Communications
AU - Kuvshinova, Sofya Sergeevna
AU - Smol'yakov, Alexander Fedorovich
AU - Vorobyeva, Daria Vladimirovna
AU - Osipov, Sergey Nikolaevich
AU - Loginov, Dmitry Alexandrovich
PY - 2018
DA - 2018/06/29
PB - Mendeleev Communications
SP - 359-361
IS - 4
VL - 28
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Kuvshinova,
author = {Sofya Sergeevna Kuvshinova and Alexander Fedorovich Smol'yakov and Daria Vladimirovna Vorobyeva and Sergey Nikolaevich Osipov and Dmitry Alexandrovich Loginov},
title = {CF3-Carbenoid functionalization of N-(pyrimidin-2-yl)indole catalyzed by cobalt complexes: Ligand control of selectivity},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.07.005},
number = {4},
pages = {359--361},
doi = {10.1016/j.mencom.2018.07.005}
}
MLA
Cite this
MLA Copy
Kuvshinova, Sofya Sergeevna, et al. “CF3-Carbenoid functionalization of N-(pyrimidin-2-yl)indole catalyzed by cobalt complexes: Ligand control of selectivity.” Mendeleev Communications, vol. 28, no. 4, Jun. 2018, pp. 359-361. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.07.005.

Abstract

The carbonyl cobalt complex Cp*Co(CO)I2 catalyzes carbenoid Co alkylation of N-(pyrimidin-2-yl)indole with methyl 3,3,3-trifluoro-2-diazopropionate regioselectively giving 2-substituted indole, while the N,N’-ligated cations [CpCo(L)I]+ (L=bipy, phen) provide 3-substitution exclusively. The structure of [CpCo(phen)I]PF6 was investigated by X-ray diffraction.

References

2.
Practical Methodologies for the Synthesis of Indoles
Humphrey G.R., Kuethe J.T.
Chemical Reviews, 2006
3.
Catalytic Functionalization of Indoles in a New Dimension
Bandini M., Eichholzer A.
Angewandte Chemie - International Edition, 2009
4.
Tsygankov A.A., Makarova M., Chusov D.
Mendeleev Communications, 2018
7.
Convenient Preparation of Indolyl Malonates via Carbenoid Insertion
Gibe R., Kerr M.A.
Journal of Organic Chemistry, 2002
10.
Rhodium(II)-Catalyzed Enantioselective C−H Functionalization of Indoles
DeAngelis A., Shurtleff V.W., Dmitrenko O., Fox J.M.
Journal of the American Chemical Society, 2011
11.
CuO/SiO2 as a simple, effective and recoverable catalyst for alkylation of indole derivatives with diazo compounds
Fraile J.M., Le Jeune K., Mayoral J.A., Ravasio N., Zaccheria F.
Organic and Biomolecular Chemistry, 2013
12.
Cu‐Catalyzed Carbenoid Functionalization of Indoles by Methyl 3,3,3‐Trifluoro‐2‐diazopropionate
Tsyshchuk I.E., Vorobyeva D.V., Peregudov A.S., Osipov S.N.
European Journal of Organic Chemistry, 2014
14.
Efficient catalytic addition of aromatic carbon-hydrogen bonds to olefins
Murai S., Kakiuchi F., Sekine S., Tanaka Y., Kamatani A., Sonoda M., Chatani N.
Nature, 1993
17.
Oxidative coupling of benzoic acids with alkynes: Catalyst design and selectivity
19.
10.1016/j.mencom.2018.07.005_sbref0030b
Vorobyeva
Eur. J. Org. Chem., 2015
21.
RhIII-Catalyzed CF3-Carbenoid C-7 Functionalization of Indolines
Iagafarova I.E., Vorobyeva D.V., Loginov D.A., Peregudov A.S., Osipov S.N.
European Journal of Organic Chemistry, 2017
23.
Synthesis of α-CF3-containing triazolyl amino acids as potential neurotransmitters via click-reaction
Vorobyeva D.V., Peregudov A.S., Röschenthaler G., Osipov S.N.
Journal of Fluorine Chemistry, 2015
24.
Fluorinated Unsymmetrical N ,N ′-Diaryl Imidazolium Salts-New Functionalized NHC-Ligand Precursors
Topchiy M.A., Zotova M.A., Masoud S.M., Mailyan A.K., Ananyev I.V., Nefedov S.E., Asachenko A.F., Osipov S.N.
Chemistry - A European Journal, 2017
25.
Synthesis of metathesis catalysts with fluorinated unsymmetrical N,N’-diaryl imidazoline-based NHC ligands
Masoud S.M., Topchiy M.A., Peregudov A.S., Roisnel T., Dixneuf P.H., Bruneau C., Osipov S.N.
Journal of Fluorine Chemistry, 2017
26.
Rhodium(iii)-catalyzed CF3-carbenoid C-H functionalization of 6-arylpurines.
Vorobyeva D.V., Vinogradov M.M., Nelyubina Y.V., Loginov D.A., Peregudov A.S., Osipov S.N.
Organic and Biomolecular Chemistry, 2018
29.
Stereoselective Alkane Oxidation with meta-Chloroperoxybenzoic Acid (MCPBA) Catalyzed by Organometallic Cobalt Complexes
Shul’pin G., Loginov D., Shul’pina L., Ikonnikov N., Idrisov V., Vinogradov M., Osipov S., Nelyubina Y., Tyubaeva P.
Molecules, 2016
30.
10.1016/j.mencom.2018.07.005_bib0050
Spek
Acta Crystallogr, 2009
31.
Cobalt(III)-Catalyzed Directed CH Coupling with Diazo Compounds: Straightforward Access towards Extended π-Systems
Zhao D., Kim J.H., Stegemann L., Strassert C.A., Glorius F.
Angewandte Chemie - International Edition, 2015
34.
Oxidative Annulation of Arenecarboxylic and Acrylic Acids with Alkynes under Ambient Conditions Catalyzed by an Electron‐Deficient Rhodium(III) Complex
Kudo E., Shibata Y., Yamazaki M., Masutomi K., Miyauchi Y., Fukui M., Sugiyama H., Uekusa H., Satoh T., Miura M., Tanaka K.
Chemistry - A European Journal, 2016
35.
Chamkin A.A., Finogenova A.M., Nelyubina Y.V., Laskova J., Kudinov A.R., Loginov D.A.
Mendeleev Communications, 2016