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Reductive α-alkylation of ketones with aldehydes at atmospheric pressure of carbon monoxide: the effect of fluoride activation in ruthenium catalysis

Alexey Anatol'evich Tsygankov 1
Alexey Anatol'evich Tsygankov
Denis Alexandrovich Chusov
1 A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
2 G.V. Plekhanov Russian University of Economics, Moscow, Russian Federation
Published 2022-12-26
CommunicationVolume 33, Issue 1, 17-20
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Runikhina S. A. et al. Reductive α-alkylation of ketones with aldehydes at atmospheric pressure of carbon monoxide: the effect of fluoride activation in ruthenium catalysis // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 17-20.
GOST all authors (up to 50) Copy
Runikhina S. A., Tsygankov A. A., Afanasyev O. I., Chusov D. A. Reductive α-alkylation of ketones with aldehydes at atmospheric pressure of carbon monoxide: the effect of fluoride activation in ruthenium catalysis // Mendeleev Communications. 2022. Vol. 33. No. 1. pp. 17-20.
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TY - JOUR
DO - 10.1016/j.mencom.2023.01.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.005
TI - Reductive α-alkylation of ketones with aldehydes at atmospheric pressure of carbon monoxide: the effect of fluoride activation in ruthenium catalysis
T2 - Mendeleev Communications
AU - Runikhina, Sofiya Alexandrovna
AU - Tsygankov, Alexey Anatol'evich
AU - Afanasyev, Oleg Ilyich
AU - Chusov, Denis Alexandrovich
PY - 2022
DA - 2022/12/26
PB - Mendeleev Communications
SP - 17-20
IS - 1
VL - 33
ER -
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@article{2022_Runikhina,
author = {Sofiya Alexandrovna Runikhina and Alexey Anatol'evich Tsygankov and Oleg Ilyich Afanasyev and Denis Alexandrovich Chusov},
title = {Reductive α-alkylation of ketones with aldehydes at atmospheric pressure of carbon monoxide: the effect of fluoride activation in ruthenium catalysis},
journal = {Mendeleev Communications},
year = {2022},
volume = {33},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.005},
number = {1},
pages = {17--20},
doi = {10.1016/j.mencom.2023.01.005}
}
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Runikhina, Sofiya Alexandrovna, et al. “Reductive α-alkylation of ketones with aldehydes at atmospheric pressure of carbon monoxide: the effect of fluoride activation in ruthenium catalysis.” Mendeleev Communications, vol. 33, no. 1, Dec. 2022, pp. 17-20. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.01.005.
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Keywords

aldehydes
aldol reaction
carbon monoxide
fluoride activation
Ketones
reductive addition
ruthenium

Abstract

Fluoride additive to [(p-cymene)RuCl2]2, a readily available ruthenium catalyst, allows one to achieve milder conditions for the reductive alkylation of aldehydes with ketones using carbon monoxide as a reducing agent. The procedure is suitable for the broad substrate scope, and a probable explanation for the fluoride role was provided.

References

2.
Recent Advances in Enantioselective Pd-Catalyzed Allylic Substitution: From Design to Applications
Pàmies O., Margalef J., Cañellas S., James J., Judge E., Guiry P.J., Moberg C., Bäckvall J., Pfaltz A., Pericàs M.A., Diéguez M.
Chemical Reviews, 2021
4.
Harnessing the Power of the Water-Gas Shift Reaction for Organic Synthesis.
Ambrosi A., Denmark S.E.
Angewandte Chemie - International Edition, 2016
12.
Towards ligand simplification in manganese-catalyzed hydrogenation and hydrosilylation processes
Gulyaeva E.S., Osipova E.S., Buhaibeh R., Canac Y., Sortais J., Valyaev D.A.
Coordination Chemistry Reviews, 2022
13.
New horizons for catalysis disclosed by supramolecular chemistry
Olivo G., Capocasa G., Del Giudice D., Lanzalunga O., Di Stefano S.
Chemical Society Reviews, 2021
14.
Molecular Complexity Calculated by Fractal Dimension
von Korff M., Sander T.
Scientific Reports, 2019
15.
Photooxygenation of 2-propargylfurans: a path to structurally diverse nitrogen-containing 5-membered rings
Marin L., Force G., Guillot R., Gandon V., Schulz E., Lebœuf D.
Chemical Communications, 2019
16.
The many roles of molecular complexity in drug discovery
Méndez-Lucio O., Medina-Franco J.L.
Drug Discovery Today, 2017
17.
Sustainable Synthesis of a Potent and Selective 5-HT7 Receptor Antagonist Using a Mechanochemical Approach
Canale V., Frisi V., Bantreil X., Lamaty F., Zajdel P.
Journal of Organic Chemistry, 2020
18.
Stereoselective Protection-Free Modification of 3-Keto-saccharides
Marinus N., Tahiri N., Duca M., Mouthaan L.M., Bianca S., van den Noort M., Poolman B., Witte M.D., Minnaard A.J.
Organic Letters, 2020
19.
Calixarene-supported Pd–NHC complexes as efficient catalysts for scalable Suzuki–Miyaura cross-couplings
Labattut A., Abi Fayssal S., Buendia J., Abdellah I., Huc V., Martini C., Schulz E.
Reaction Chemistry and Engineering, 2020
20.
Site-selective nitrenoid insertions utilizing postfunctionalized bifunctional rhodium(ii) catalysts
Berndt J., Radchenko Y., Becker J., Logemann C., Bhandari D.R., Hrdina R., Schreiner P.R.
Chemical Science, 2019
22.
Aldehydes as Alkylating Agents for Ketones
Runikhina S.A., Afanasyev O.I., Biriukov K., Perekalin D.S., Klussmann M., Chusov D.
Chemistry - A European Journal, 2019
24.
Palladium/iodide catalyzed oxidative carbonylation of aniline to diphenylurea: Effect of ppm amounts of iron salts
25.
Reductive Amidation without an External Hydrogen Source Using Rhodium on Carbon Matrix as a Catalyst
Tsygankov A.A., Makarova M., Afanasyev O.I., Kashin A.S., Naumkin A.V., Loginov D.A., Chusov D.
ChemCatChem, 2019
27.
Gold and Silver-Catalyzed Reductive Amination of Aromatic Carboxylic Acids to Benzylic Amines
Coeck R., Meeprasert J., Li G., Altantzis T., Bals S., Pidko E.A., De Vos D.E.
ACS Catalysis, 2021
28.
Reductive Aldol‐type Reactions in the Synthesis of Pharmaceuticals
Runikhina S., Eremin D., Chusov D.
Chemistry - A European Journal, 2021
30.
The preparation and crystal structure of a ruthenium carbonyl fluoride [Ru(CO)3F2]4
Marshall C.J., Peacock R.D., Russell D.R., Wilson I.L.
Journal of the Chemical Society D Chemical Communications, 1970
31.
Synthesis and characterisation of ruthenium carbonyl fluorides
Coleman K.S., Holloway J.H., Hope E.G.
Journal of the Chemical Society Dalton Transactions, 1997
33.
Fluorine as a Hydrogen-Bond Acceptor: Experimental Evidence and Computational Calculations
Dalvit C., Invernizzi C., Vulpetti A.
Chemistry - A European Journal, 2014
34.
Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure–activity relationship study
Ivković B.M., Nikolic K., Ilić B.B., Žižak Ž.S., Novaković R.B., Čudina O.A., Vladimirov S.M.
European Journal of Medicinal Chemistry, 2013
35.
Philippova A.N., Vorobyeva D.V., Vasilyeva T.P., Mailyan A.K., Gribanov P.S., Osipov S.N.
Mendeleev Communications, 2022
36.
Shepelenko K.E., Nikolaeva K.A., Shevchenko M.A., Tkachenko Y.N., Minyaev M.E., Chernyshev V.M.
Mendeleev Communications, 2022