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Cationic palladium(II)-acetylacetonate complexes bearing pyridinyl imine ligands as catalysts for the hydroamination of phenylacetylene and polymerization of norbornene

Dmitrii Sergeevich Suslov 1
Dmitrii Sergeevich Suslov
Anastasia Vyacheslavovna Suchkova 1
Anastasia Vyacheslavovna Suchkova
Mikhail Valer'evich Bykov 1
Mikhail Valer'evich Bykov
Zorikto Danilovich Abramov 1
Zorikto Danilovich Abramov
Marina Vladimirovna Pakhomova 1
Marina Vladimirovna Pakhomova
Timur Sergeevich Orlov 1
Timur Sergeevich Orlov
Igor Alekseevich Ushakov 2
Igor Alekseevich Ushakov
Tatyana Nikolaevna Borodina 2
Tatyana Nikolaevna Borodina
Vladimir Ilyich Smirnov 2
Vladimir Ilyich Smirnov
1 Research Institute of Oil and Coal Chemical Synthesis, Irkutsk State University, Irkutsk, Russian Federation
Published 2023-02-13
CommunicationVolume 33, Issue 2, 184-187
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Suslov D. S. et al. Cationic palladium(II)-acetylacetonate complexes bearing pyridinyl imine ligands as catalysts for the hydroamination of phenylacetylene and polymerization of norbornene // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 184-187.
GOST all authors (up to 50) Copy
Suslov D. S., Suchkova A. V., Bykov M. V., Abramov Z. D., Pakhomova M. V., Orlov T. S., Ushakov I. A., Borodina T. N., Smirnov V. I. Cationic palladium(II)-acetylacetonate complexes bearing pyridinyl imine ligands as catalysts for the hydroamination of phenylacetylene and polymerization of norbornene // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 184-187.
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TY - JOUR
DO - 10.1016/j.mencom.2023.02.011
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.011
TI - Cationic palladium(II)-acetylacetonate complexes bearing pyridinyl imine ligands as catalysts for the hydroamination of phenylacetylene and polymerization of norbornene
T2 - Mendeleev Communications
AU - Suslov, Dmitrii Sergeevich
AU - Suchkova, Anastasia Vyacheslavovna
AU - Bykov, Mikhail Valer'evich
AU - Abramov, Zorikto Danilovich
AU - Pakhomova, Marina Vladimirovna
AU - Orlov, Timur Sergeevich
AU - Ushakov, Igor Alekseevich
AU - Borodina, Tatyana Nikolaevna
AU - Smirnov, Vladimir Ilyich
PY - 2023
DA - 2023/02/13
PB - Mendeleev Communications
SP - 184-187
IS - 2
VL - 33
ER -
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@article{2023_Suslov,
author = {Dmitrii Sergeevich Suslov and Anastasia Vyacheslavovna Suchkova and Mikhail Valer'evich Bykov and Zorikto Danilovich Abramov and Marina Vladimirovna Pakhomova and Timur Sergeevich Orlov and Igor Alekseevich Ushakov and Tatyana Nikolaevna Borodina and Vladimir Ilyich Smirnov},
title = {Cationic palladium(II)-acetylacetonate complexes bearing pyridinyl imine ligands as catalysts for the hydroamination of phenylacetylene and polymerization of norbornene},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.011},
number = {2},
pages = {184--187},
doi = {10.1016/j.mencom.2023.02.011}
}
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Cite this
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Suslov, Dmitrii Sergeevich, et al. “Cationic palladium(II)-acetylacetonate complexes bearing pyridinyl imine ligands as catalysts for the hydroamination of phenylacetylene and polymerization of norbornene.” Mendeleev Communications, vol. 33, no. 2, Feb. 2023, pp. 184-187. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.011.

Keywords

acetylacetonate
hydroamination
imines
norbornene
palladium
phenylacetylene
polymerization.
pyridines

Abstract

Acetylacetonate palladium(II) complexes bearing pyridinyl imine ligands [Pd(acac)(L)]BF4 were synthesized via nitrile displacement in [Pd(acac)(MeCN)2]BF4 by the bidentate ligands L of type 2-C5H4N-CH=N-(CH2)nOMe or 2-C5H4N-CH=N-Ar. The structures of complexes were analyzed by X-ray diffractometry, NMR, and DFT. The complexes catalyze hydroamination of phenylacetylene with aniline to give the Markovnikov imine product as well as polymerization of norbornene.

References

.
Advances in Non-Metallocene Olefin Polymerization Catalysis
Gibson V.C., Spitzmesser S.K.
Chemical Reviews, 2002
.
Late Transition Metal-Catalyzed Hydroamination and Hydroamidation
Huang L., Arndt M., Gooßen K., Heydt H., Gooßen L.J.
Chemical Reviews, 2015
.
Metal catalysts for the vinyl/addition polymerization of norbornene
.
Late-Metal Catalysts for Ethylene Homo- and Copolymerization
Ittel S.D., Johnson L.K., Brookhart M.
Chemical Reviews, 2000
.
New Pd(II)- and Ni(II)-Based Catalysts for Polymerization of Ethylene and .alpha.-Olefins
Johnson L.K., Killian C.M., Brookhart M.
Journal of the American Chemical Society, 1995
.
NMR study on the coordination behavior of dissymmetric terdentate trinitrogen ligands on methylpalladium(II) compounds
Rulke R.E., Ernsting J.M., Spek A.L., Elsevier C.J., van Leeuwen P.W., Vrieze K.
Inorganic Chemistry, 1993
.
Cationic acetylacetonate palladium complexes/boron trifluoride etherate catalyst systems for hydroamination of vinylarenes using arylamines
Suslov D.S., Bykov M.V., Pakhomova M.V., Abramov P.A., Ushakov I.A., Tkach V.S.
Catalysis Communications, 2017
.
Synthesis of dialkyl, diaryl and metallacyclic complexes of Ni and Pd containing pyridine, α-diimines and other nitrogen ligands
Cámpora J., del Mar Conejo M., Mereiter K., Palma P., Pérez C., Reyes M.L., Ruiz C.
Journal of Organometallic Chemistry, 2003
.
PdI2 as a Simple and Efficient Catalyst for the Hydroamination of Arylacetylenes with Anilines
Casnati A., Voronov A., Ferrari D.G., Mancuso R., Gabriele B., Motti E., Della Ca’ N.
Catalysts, 2020
.
Hydroamination of Aromatic Alkynes to Imines Catalyzed by Pd(II)–Anthraphos Complexes
Erken C., Hindemith C., Weyhermüller T., Hölscher M., Werlé C., Leitner W.
ACS Omega, 2020
.
Pyridine Wingtip in [Pd(Py-tzNHC)2]2+ Complex Is a Proton Shuttle in the Catalytic Hydroamination of Alkynes
Virant M., Mihelač M., Gazvoda M., Cotman A.E., Frantar A., Pinter B., Košmrlj J.
Organic Letters, 2020
.
Synthesis of mononuclear and dinuclear palladium (II) complexes containing oxadithioether ligands and their catalytic activities in norbornene polymerization
Suslov D.S., Abramov Z.D., Babenko I.A., Bezborodov V.A., Borodina T.N., Bykov M.V., Pakhomova M.V., Smirnov V.I., Suchkova A.V., Ratovskii G.V., Ushakov I.A., Vilms A.I.
Applied Organometallic Chemistry, 2021
.
Bis-alkoxycarbonylation of styrene by pyridinimine palladium catalysts
Bianchini C., Man Lee H., Mantovani G., Meli A., Oberhauser W.
New Journal of Chemistry, 2002
.
Simple, efficient and reusable Pd–NHC catalysts for hydroamination
Chen Q., Lv L., Yu M., Shi Y., Li Y., Pang G., Cao C.
RSC Advances, 2013
.
Palladium complexes with simple iminopyridines as catalysts for polyketone synthesis
Rosar V., Dedeic D., Nobile T., Fini F., Balducci G., Alessio E., Carfagna C., Milani B.
Dalton Transactions, 2016
.
Pyridinylimine-based nickel(II) and palladium(II) complexes: preparation, structural characterization and use as alkene polymerization catalysts
Laine T.V., Piironen U., Lappalainen K., Klinga M., Aitola E., Leskelä M.
Journal of Organometallic Chemistry, 2000
.
Oligomerisation of Ethylene by Bis(imino)pyridyliron and -cobalt Complexes
Britovsek G.J., Mastroianni S., Solan G.A., Baugh S.P., Redshaw C., Gibson V.C., White A.J., Williams D.J., Elsegood M.R.
Chemistry - A European Journal, 2000
.
Nucleophilic Attack on Coordinated Imines: The Synthesis of C‐Bonded Acetylacetonates of Palladium(II) and Mechanistic Insights
Birkle T., Carbayo A., Cuevas J.V., García‐Herbosa G., Muñoz A.
European Journal of Inorganic Chemistry, 2012
.
Vinyl polymerization of norbornene with dinuclear diimine nickel dichloride/MAO
Mi X., Ma Z., Cui N., Wang L., Ke Y., Hu Y.
Journal of Applied Polymer Science, 2003
.
15N NMR studies on cyclopalladated Schiff's base complexes
Pregosin P.S., Rüedi R., Anklin C.
Magnetic Resonance in Chemistry, 1986
.
Synthesis, characterization, and application for addition polymerization of norbornene of novel acetylacetonate bis(anilines) palladium (II) complexes
Suslov D.S., Bykov M.V., Abramov P.A., Pakhomova M.V., Ushakov I.A., Voronov V.K., Tkach V.S.
Inorganic Chemistry Communication, 2016
.
Cationic acetylacetonate palladium complexes/boron trifluoride etherate catalyst systems for polymerization of 5-methoxycarbonylnorbornene
Suslov D.S., Bykov M.V., Kuzmin A.V., Abramov P.A., Kravchenko O.V., Pakhomova M.V., Rokhin A.V., Ushakov I.A., Tkach V.S.
Catalysis Communications, 2018
.
Palladium(II) complexes of (pyridyl)imine ligands as catalysts for the methoxycarbonylation of olefins
Zulu Z., Nyamato G.S., Tshabalala T.A., Ojwach S.O.
Inorganica Chimica Acta, 2020
.
Cationic palladium(II)–acetylacetonate complexes containing phosphine and aminophosphine ligands and their catalytic activities in telomerization of 1,3-butadiene with methanol
Suslov D.S., Bykov M.V., Abramov Z.D., Ushakov I.A., Borodina T.N., Smirnov V.I., Ratovskii G.V., Tkach V.S.
Journal of Organometallic Chemistry, 2020
.
An effective route for the synthesis of cationic palladium complexes of general formula [(Acac)PdL1L2]+A−
Tkach V.S., Suslov D.S., Myagmarsuren G., Ratovskii G.V., Rohin A.V., Felix T., Shmidt F.K.
Journal of Organometallic Chemistry, 2008