Home / Publications / 2-Halopyridines in the triple reaction in the Pn/KOH/DMSO system to form tri(2-pyridyl)phosphine: Experimental and quantum-chemical dissimilarities

2-Halopyridines in the triple reaction in the Pn/KOH/DMSO system to form tri(2-pyridyl)phosphine: Experimental and quantum-chemical dissimilarities

Svetlana Filippovna Malysheva 1
Svetlana Filippovna Malysheva
, 
Vladimir Anatol'evich Kuimov 1
Vladimir Anatol'evich Kuimov
, 
Alexander Borisovich Trofimov 1
Alexander Borisovich Trofimov
, 
Natalia Alekseevna Belogorlova 1
Natalia Alekseevna Belogorlova
, 
Yuriy Igorevich Litvintsev 1
Yuriy Igorevich Litvintsev
, 
Alexandra Maksimovna Belogolova 1
Alexandra Maksimovna Belogolova
, 
Nina Kuzminichna Gusarova 1
Nina Kuzminichna Gusarova
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2018.09.006
Published 2018-09-07
Communication , Volume 28, Issue 5, 472-474
15
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Malysheva S. F. et al. 2-Halopyridines in the triple reaction in the Pn/KOH/DMSO system to form tri(2-pyridyl)phosphine: Experimental and quantum-chemical dissimilarities // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 472-474.
GOST all authors (up to 50) Copy
Malysheva S. F., Kuimov V. A., Trofimov A. B., Belogorlova N. A., Litvintsev Y. I., Belogolova A. M., Gusarova N. K., Trofimov B. A. 2-Halopyridines in the triple reaction in the Pn/KOH/DMSO system to form tri(2-pyridyl)phosphine: Experimental and quantum-chemical dissimilarities // Mendeleev Communications. 2018. Vol. 28. No. 5. pp. 472-474.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2018.09.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.006
TI - 2-Halopyridines in the triple reaction in the Pn/KOH/DMSO system to form tri(2-pyridyl)phosphine: Experimental and quantum-chemical dissimilarities
T2 - Mendeleev Communications
AU - Malysheva, Svetlana Filippovna
AU - Kuimov, Vladimir Anatol'evich
AU - Trofimov, Alexander Borisovich
AU - Belogorlova, Natalia Alekseevna
AU - Litvintsev, Yuriy Igorevich
AU - Belogolova, Alexandra Maksimovna
AU - Gusarova, Nina Kuzminichna
AU - Trofimov, Boris Aleksandrovich
PY - 2018
DA - 2018/09/07
PB - Mendeleev Communications
SP - 472-474
IS - 5
VL - 28
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2018_Malysheva,
author = {Svetlana Filippovna Malysheva and Vladimir Anatol'evich Kuimov and Alexander Borisovich Trofimov and Natalia Alekseevna Belogorlova and Yuriy Igorevich Litvintsev and Alexandra Maksimovna Belogolova and Nina Kuzminichna Gusarova and Boris Aleksandrovich Trofimov},
title = {2-Halopyridines in the triple reaction in the Pn/KOH/DMSO system to form tri(2-pyridyl)phosphine: Experimental and quantum-chemical dissimilarities},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.006},
number = {5},
pages = {472--474},
doi = {10.1016/j.mencom.2018.09.006}
}
MLA
Cite this
MLA Copy
Malysheva, Svetlana Filippovna, et al. “2-Halopyridines in the triple reaction in the Pn/KOH/DMSO system to form tri(2-pyridyl)phosphine: Experimental and quantum-chemical dissimilarities.” Mendeleev Communications, vol. 28, no. 5, Sep. 2018, pp. 472-474. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.09.006.

Abstract

Experimental and quantum-chemical features of the triple nucleophilic substitution of halogen atoms in 2-chloro- and 2-bromopyridines under the action of P-centered nucleophiles generated in the system Pn/KOH/DMSO to afford tri(2-pyridyl)phosphine in a yield of up to 69% have been compared.

References

1.
A new class of luminescent Cu(i) complexes with tripodal ligands – TADF emitters for the yellow to red color range
Gneuß T., Leitl M.J., Finger L.H., Rau N., Yersin H., Sundermeyer J.
Dalton Transactions, 2015
2.
Sterically-constrained tripodal phosphorus-bridged tris-pyridyl ligands
Hanf S., García-Rodríguez R., Bond A.D., Hey-Hawkins E., Wright D.S.
Dalton Transactions, 2016
3.
Variable coordination of tris(2-pyridyl)phosphine and its oxide toward M(hfac)2: a metal-specifiable switching between the formation of mono- and bis-scorpionate complexes
Artem'ev A.V., Kashevskii A.V., Bogomyakov A.S., Safronov A.Y., Sutyrina A.O., Telezhkin A.A., Sterkhova I.V.
Dalton Transactions, 2017
4.
Tris(2-pyridyl)phosphine as a versatile ligand for pnictogen acceptors
Suter R., Sinclair H., Burford N., McDonald R., Ferguson M.J., Schrader E.
Dalton Transactions, 2017
5.
A new family of clusters containing a silver-centered tetracapped [Ag@Ag4(μ3-P)4] tetrahedron, inscribed within a N12 icosahedron
Artem'ev A.V., Bagryanskaya I.Y., Doronina E.P., Tolstoy P.M., Gushchin A.L., Rakhmanova M.I., Ivanov A.Y., Suturina A.O.
Dalton Transactions, 2017
6.
Iron(II) and cobalt(II) tris(2-pyridyl)phosphine and tris(2-pyridyl)amine catalysts for the ethylene polymerization
Karam A., Tenia R., Martínez M., López-Linares F., Albano C., Diaz-Barrios A., Sánchez Y., Catarí E., Casas E., Pekerar S., Albornoz A.
Journal of Molecular Catalysis A Chemical, 2007
7.
Hydrogenation of α,β-unsaturated substrates by tris(2-phridyl)amine (tpN) or tris(2-pyridyl)phosphine (tpP)/[Ir(COE)2Cl]2 catalyst systems
López-Linares F., Fuentes A., Tenia R., Martinez M., Karam A.
Reaction Kinetics and Catalysis Letters, 2007
9.
D.W. Norman, J.L. Laningham, Patent US 20150080628, 2015.(Chem. Abstr., 2015, 162, 438977).
10.
T. Gneuß, J. Sundermeyer, M. Leitl, H. Yersin, Patent DE 102014116314, 2016.(Chem. Abstr., 2016, 164, 609200).
11.
Luminescent CuI thiocyanate complexes based on tris(2-pyridyl)phosphine and its oxide: from mono-, di- and trinuclear species to coordination polymers
Artem’ev A.V., Doronina E.P., Rakhmanova M.I., Sutyrina A.O., Bagryanskaya I.Y., Tolstoy P.M., Gushchin A.L., Mazur A.S., Gusarova N.K., Trofimov B.A.
New Journal of Chemistry, 2016
12.
T. Hanyu, Patent JP 2003057783, 2003.(Chem. Abstr., 2003, 138, 195810).
13.
K. Amine, L. Zhang, Z. Zhang, Patent US 20140272607, 2014.(Chem. Abstr., 2014, 161, 477212).
14.
In vitro antitumour and hepatotoxicity profiles of Au(I) and Ag(I) bidentate pyridyl phosphine complexes and relationships to cellular uptake.
Liu J.J., Galettis P., Farr A., Maharaj L., Samarasinha H., McGechan A.C., Baguley B.C., Bowen R.J., Berners-Price S.J., McKeage M.J.
Journal of Inorganic Biochemistry, 2008
16.
Molecular Structure and Antimicrobial Activity of a Luminescent Dinuclear Silver(I) Complex of Phenyl-bis(2-pyridyl)phosphine
Nemati Kharat A., Bakhoda A., Foroutannejad S., Foroutannejad C.
Zeitschrift fur Anorganische und Allgemeine Chemie, 2011
17.
Luminescent Ag(I) scorpionates based on tris(2-pyridyl)phosphine oxide: Synthesis and cytotoxic activity evaluation
Artem'ev A.V., Eremina J.A., Lider E.V., Antonova O.V., Vorontsova E.V., Bagryanskaya I.Y.
Polyhedron, 2017
18.
Reaction of Tri(2-pyridyl)phosphine with Electron-Deficient Alkynes in Water: Stereoselective Synthesis of Functionalized Pyridylvinylphosphine Oxides
Arbuzova S.N., Gusarova N.K., Glotova T.E., Ushakov I.A., Verkhoturova S.I., Korocheva A.O., Trofimov B.A.
European Journal of Organic Chemistry, 2013
19.
P-C Bond Cleavage by Hydroxyl Function during the Addition of Tris(2-pyridyl)phosphine to Cyanopropargylic Alcohols in Water
Arbuzova S.N., Gusarova N.K., Verkhoturova S.I., Kazantseva T.I., Ushakov I.A., Mal'kina A.G., Trofimov B.A.
Heteroatom Chemistry, 2015
21.
Efficient One-Pot Synthesis of Mono- and Bis[di(2-pyridyl)phosphine Oxides] from Tris(2-pyridyl)phosphine
Artem’ev A., Malysheva S., Gusarova N., Belogorlova N., Sutyrina A., Litvintsev Y., Albanov A., Sterkhova I.
Synlett, 2016
22.
Gusarova N.K., Volkov P.A., Ivanova N.I., Khrapova K.O., Telezhkin A.A., Albanov A.I., Trofimov B.A.
Mendeleev Communications, 2017
26.
Vereshchagin A.N., Elinson M.N., Anisina Y.E., Ryzhkov F.V., Goloveshkin A.S., Bushmarinov I.S., Zlotin S.G., Egorov M.P.
Mendeleev Communications, 2015
27.
One-Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF3 -Ynones
Romanov A.R., Rulev A.Y., Ushakov I.A., Muzalevskiy V.M., Nenajdenko V.G.
European Journal of Organic Chemistry, 2017
28.
PASE Pseudo-Four-Component Synthesis and Docking Studies of New 5-C-Substituted 2,4-Diamino-5H-Chromeno[2,3-b]pyridine-3-Carbonitriles
Vereshchagin A.N., Elinson M.N., Anisina Y.E., Ryzhkov F.V., Novikov R.A., Egorov M.P.
ChemistrySelect, 2017
29.
Expedient one-pot organometallics-free synthesis of tris(2-pyridyl)phosphine from 2-bromopyridine and elemental phosphorus
Trofimov B.A., Artem’ev A.V., Malysheva S.F., Gusarova N.K., Belogorlova N.A., Korocheva A.O., Gatilov Y.V., Mamatyuk V.I.
Tetrahedron Letters, 2012
30.
Trofimov B.A., Gusarova N.K., Artem’ev A.V., Malysheva S.F., Belogorlova N.A., Korocheva A.O., Kazheva O.N., Alexandrov G.G., Dyachenko O.A.
Mendeleev Communications, 2012
31.
Elemental phosphorus–strong base as a system for the synthesis of organophosphorus compounds
Trofimov B.A., Rakhmatulina T.N., Gusarova N.K., Malysheva S.F.
Russian Chemical Reviews, 1991
33.
Novel general halogen-free methodology for the synthesis of organophosphorus compounds
Gusarova N.K., Arbuzova S.N., Trofimov B.A.
Pure and Applied Chemistry, 2012
34.
The reaction of red phosphorus with 1-bromonaphthalene in the KOH-DMSO system: Synthesis of tri(1-naphthyl)phosphane
Kuimov V.A., Malysheva S.F., Gusarova N.K., Vakul'skaya T.I., Khutsishvili S.S., Trofimov B.A.
Heteroatom Chemistry, 2011
35.
Ionization of pyridine: Interplay of orbital relaxation and electron correlation
Trofimov A.B., Holland D.M., Powis I., Menzies R.C., Potts A.W., Karlsson L., Gromov E.V., Badsyuk I.L., Schirmer J.
Journal of Chemical Physics, 2017
36.
An experimental and theoretical study of the valence shell photoelectron spectra of 2-chloropyridine and 3-chloropyridine
Holland D.M., Powis I., Trofimov A.B., Menzies R.C., Potts A.W., Karlsson L., Badsyuk I.L., Moskovskaya T.E., Gromov E.V., Schirmer J.
Journal of Chemical Physics, 2017
37.
Artem’ev A.V., Gusarova N.K., Korocheva A.O., Malysheva S.F., Gatilov Y.V., Trofimov B.A.
Mendeleev Communications, 2014
38.
The Direct Phosphorylation Of 2-, 3-, and 4-Methylstyrenes and 2,4,6-Trimethylstyrene with Elemental Phosphorus VIA Trofimov–Gusarova Reaction
Artem’ev A.V., Korocheva A.O., Vashchenko A.V., Smirnov V.I., Malysheva S.F.
Phosphorus, Sulfur and Silicon and the Related Elements, 2015
39.
Reaction of elemental phosphorus with α-methylstyrenes: one-pot synthesis of secondary and tertiary phosphines, prospective bulky ligands for Pd(II) catalysts
Artem'ev A.V., Malysheva S.F., Gusarova N.K., Belogorlova N.A., Sukhov B.G., Sutyrina A.O., Matveeva E.A., Vasilevsky S.F., Govdi A.I., Gatilov Y.V., Albanov A.I., Trofimov B.A.
Tetrahedron, 2016