Home / Publications / Nitrogen ligand influence on the CO-assisted ruthenium-catalyzed reductive amination

Nitrogen ligand influence on the CO-assisted ruthenium-catalyzed reductive amination

Andrey Sergeyevich Kozlov 1
Andrey Sergeyevich Kozlov
,  , 
Mikhail Andreevich Losev 1, 2
Mikhail Andreevich Losev
, 
Maria Igorevna Godovikova 1
Maria Igorevna Godovikova
, 
Denis Alexandrovich Chusov 1, 3
Denis Alexandrovich Chusov
1 A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
2 National Research University Higher School of Economics (HSE University), Moscow, Russian Federation
3 G.V. Plekhanov Russian University of Economics, Moscow, Russian Federation
10.1016/j.mencom.2023.02.008
Published 2023-02-13
Communication , Volume 33, Issue 2, 174-176
0
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Kozlov A. S. et al. Nitrogen ligand influence on the CO-assisted ruthenium-catalyzed reductive amination // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 174-176.
GOST all authors (up to 50) Copy
Kozlov A. S., Afanasyev O. I., Losev M. A., Godovikova M. I., Chusov D. A. Nitrogen ligand influence on the CO-assisted ruthenium-catalyzed reductive amination // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 174-176.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2023.02.008
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.008
TI - Nitrogen ligand influence on the CO-assisted ruthenium-catalyzed reductive amination
T2 - Mendeleev Communications
AU - Kozlov, Andrey Sergeyevich
AU - Afanasyev, Oleg Ilyich
AU - Losev, Mikhail Andreevich
AU - Godovikova, Maria Igorevna
AU - Chusov, Denis Alexandrovich
PY - 2023
DA - 2023/02/13
PB - Mendeleev Communications
SP - 174-176
IS - 2
VL - 33
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2023_Kozlov,
author = {Andrey Sergeyevich Kozlov and Oleg Ilyich Afanasyev and Mikhail Andreevich Losev and Maria Igorevna Godovikova and Denis Alexandrovich Chusov},
title = {Nitrogen ligand influence on the CO-assisted ruthenium-catalyzed reductive amination},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.008},
number = {2},
pages = {174--176},
doi = {10.1016/j.mencom.2023.02.008}
}
MLA
Cite this
MLA Copy
Kozlov, Andrey Sergeyevich, et al. “Nitrogen ligand influence on the CO-assisted ruthenium-catalyzed reductive amination.” Mendeleev Communications, vol. 33, no. 2, Feb. 2023, pp. 174-176. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.008.

Keywords

aldehydes
amines
carbon monoxide
catalysis.
nitrogen-containing ligands
reductive amination
ruthenium

Abstract

A representative set of amines and N-heterocycles was applied as additives in the CO-assisted Ru-catalyzed reductive amination of p-anisaldehyde with p-anisidine. Among the tested ligands, pyridine caused a strong activation for low active aliphatic substrates while bidentate heterocyclic ligands possess significant inhibition of catalyst for the majority of substrates.

References

.
Harnessing the Power of the Water-Gas Shift Reaction for Organic Synthesis.
Ambrosi A., Denmark S.E.
Angewandte Chemie - International Edition, 2016
.
Philippova A.N., Vorobyeva D.V., Vasilyeva T.P., Mailyan A.K., Gribanov P.S., Osipov S.N.
Mendeleev Communications, 2022
.
3d Transition Metals for C–H Activation
Gandeepan P., Müller T., Zell D., Cera G., Warratz S., Ackermann L.
Chemical Reviews, 2018
.
Asymmetric Aminocatalysis-Gold Rush in Organic Chemistry
Melchiorre P., Marigo M., Carlone A., Bartoli G.
Angewandte Chemie - International Edition, 2008
.
Organocatalysis—after the gold rush
Bertelsen S., Jørgensen K.A.
Chemical Society Reviews, 2009
.
Levin V.V., Struchkova M.I., Dilman A.D.
Mendeleev Communications, 2017
.
Reductive Amination in the Synthesis of Pharmaceuticals.
Afanasyev O.I., Kuchuk E., Usanov D.L., Chusov D.
Chemical Reviews, 2019
.
Synthesis of Polyamines, Their Derivatives, Analogues and Conjugates
Kuksa V., Buchan R., Kong Thoo Lin P.
Synthesis, 2000
.
Amines, Aliphatic
Roose P., Eller K., Henkes E., Rossbacher R., Höke H.
2015
.
Hitchhiker’s Guide to Reductive Amination
Podyacheva E., Afanasyev O.I., Tsygankov A.A., Makarova M., Chusov D.
Synthesis, 2019
.
Bardonov D.A., Puntus L.N., Taidakov I.V., Varaksina E.A., Lyssenko K.A., Nifant'ev I.E., Roitershtein D.M.
Mendeleev Communications, 2022
.
Catalytic reductive aminations using molecular hydrogen for synthesis of different kinds of amines.
Murugesan K., Senthamarai T., Chandrashekhar V.G., Natte K., Kamer P.C., Beller M., Jagadeesh R.V.
Chemical Society Reviews, 2020
.
Reductive amination without an external hydrogen Source.
Chusov D., List B.
Angewandte Chemie - International Edition, 2014
.
Reductive amination catalyzed by iridium complexes using carbon monoxide as a reducing agent.
Moskovets A.P., Usanov D.L., Afanasyev O.I., Fastovskiy V.A., Molotkov A.P., Muratov K.M., Denisov G.L., Zlotskii S.S., Smol'yakov A.F., Loginov D.A., Chusov D.
Organic and Biomolecular Chemistry, 2017
.
Carbon monoxide-driven osmium catalyzed reductive amination harvesting WGSR power
Biriukov K.O., Vinogradov M.M., Afanasyev O.I., Vasilyev D.V., Tsygankov A.A., Godovikova M., Nelyubina Y.V., Loginov D.A., Chusov D.
Catalysis Science and Technology, 2021
.
Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures1
Abdel-Magid A.F., Carson K.G., Harris B.D., Maryanoff C.A., Shah R.D.
Journal of Organic Chemistry, 1996
.
On the Basicity of Conjugated Nitrogen Heterocycles in Different Media
Lõkov M., Tshepelevitsh S., Heering A., Plieger P.G., Vianello R., Leito I.
European Journal of Organic Chemistry, 2017
.
Korshunov V.M., Chmovzh T.N., Chkhetiani G.R., Taydakov I.V., Rakitin O.A.
Mendeleev Communications, 2022
.
Vlasenko E.S., Nikovskiy I.A., Nelyubina Y.V., Korlyukov A.A., Novikov V.V.
Mendeleev Communications, 2022
.
Phosphine ligands in the ruthenium-catalyzed reductive amination without an external hydrogen source
Makarova M., Afanasyev O.I., Kliuev F., Nelyubina Y.V., Godovikova M., Chusov D.
Journal of Organometallic Chemistry, 2021
.
Afanasyev O.I., Cherkashchenko I., Kuznetsov A., Kliuev F., Semenov S., Chusova O., Denisov G., Chusov D.
Mendeleev Communications, 2020
.
Trainov K.P., Salikov R.F., Luponosov Y.N., Savchenko P.S., Mannanov A.L., Ponomarenko S.A., Platonov D.N., Tomilov Y.V.
Mendeleev Communications, 2019
.
Fateeva A.A., Shutkov I.A., Mazur D.M., Kovaleva O.N., Milaeva E.R., Nazarov A.A.
Mendeleev Communications, 2022
.
Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers
Jakubczyk M., Mkrtchyan S., Shkoor M., Lanka S., Budzák Š., Iliaš M., Skoršepa M., Iaroshenko V.O.
Journal of the American Chemical Society, 2022
.
Synthesis of Bis(β‐Oximinoalkyl)malonates and Their Catalytic Reductive Cyclization to Piperidines
Pospelov E.V., Boyko Y.D., Ioffe S.L., Sukhorukov A.Y.
Advanced Synthesis and Catalysis, 2022
.
Synthesis of secondary amines
Salvatore R.N., Yoon C.H., Jung K.W.
Tetrahedron, 2001
.
Gribov P.S., Mikhailova M.V., Kon'kova T.S., Matyushin Y.N., Sheremetev A.B.
Mendeleev Communications, 2022