Home / Publications / Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free ‘green’ organophosphorus chemistry

Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free ‘green’ organophosphorus chemistry

Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
, 
Nina Kuzminichna Gusarova 1
Nina Kuzminichna Gusarova
10.1016/j.mencom.2009.11.001
Published 2009-11-02
Focus article , Volume 19, Issue 6, 295-302
98
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Trofimov B. A., Gusarova N. K. Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free ‘green’ organophosphorus chemistry // Mendeleev Communications. 2009. Vol. 19. No. 6. pp. 295-302.
GOST all authors (up to 50) Copy
Trofimov B. A., Gusarova N. K. Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free ‘green’ organophosphorus chemistry // Mendeleev Communications. 2009. Vol. 19. No. 6. pp. 295-302.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2009.11.001
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.11.001
TI - Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free ‘green’ organophosphorus chemistry
T2 - Mendeleev Communications
AU - Trofimov, Boris Aleksandrovich
AU - Gusarova, Nina Kuzminichna
PY - 2009
DA - 2009/11/02
PB - Mendeleev Communications
SP - 295-302
IS - 6
VL - 19
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2009_Trofimov,
author = {Boris Aleksandrovich Trofimov and Nina Kuzminichna Gusarova},
title = {Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free ‘green’ organophosphorus chemistry},
journal = {Mendeleev Communications},
year = {2009},
volume = {19},
publisher = {Mendeleev Communications},
month = {Nov},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.11.001},
number = {6},
pages = {295--302},
doi = {10.1016/j.mencom.2009.11.001}
}
MLA
Cite this
MLA Copy
Trofimov, Boris Aleksandrovich, and Nina Kuzminichna Gusarova. “Elemental phosphorus in strongly basic media as phosphorylating reagent: a dawn of halogen-free ‘green’ organophosphorus chemistry.” Mendeleev Communications, vol. 19, no. 6, Nov. 2009, pp. 295-302. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2009.11.001.
Views / Downloads
1 / 2

Abstract

The elemental phosphorus/strong bases systems are gaining a growing attention as halogen-free ‘green’ phosphorylating reagents enabling a great variety of alkenes, acetylenes, organic halides and oxiranes to be converted in one-pot procedures to inaccessible primary, secondary and tertiary phosphines and phosphine oxides.

References

1.
M. K. Whittlesey, in Organometallic Chemistry, ed. M. Green, The Royal Society of Chemistry, London, 2000, vol. 28, p. 367.
3.
Multiphase Systems for the Recycling of Alkoxycarbonylation Catalysts
de Pater J.J., Deelman B., Elsevier C., van Koten G.
Advanced Synthesis and Catalysis, 2006
5.
Modular Synthesis of ChiraClick Ligands:  A Library of P-Chirogenic Phosphines
Dolhem F., Johansson M.J., Antonsson T., Kann N.
Journal of Combinatorial Chemistry, 2007
6.
Trofimov B.A., Vasilevsky S.F., Gusarova N.K., Malysheva S.F., Baranov D.S., Mamatyuk V.I., Gatilov Y.V.
Mendeleev Communications, 2008
7.
Flame retardant epoxy resins based on diglycidyl ether of isobutyl bis(hydroxypropyl)phosphine oxide
Ribera G., Mercado L.A., Galià M., Cádiz V.
Journal of Applied Polymer Science, 2005
8.
10.1016/j.mencom.2009.11.001_bib2_2
Plotnikova
Zh. Prikl. Khim., 2008
11.
Uranium(VI) extraction by Winsor II microemulsion systems using trialkyl phosphine oxide
Shan Z., Yan-zhao Y., Tao Z., Jian H., Chang-Hong L.
Journal of Radioanalytical and Nuclear Chemistry, 2005
12.
10.1016/j.mencom.2009.11.001_bib3_4
Men'shikov
Zh. Prikl. Khim., 2009
13.
The Chemistry of Nanomaterials, eds. C. N. R. Rao, A. Müller and A. K. Cheetham, Wiley-VCH, New York, 2004, vol. 2.
14.
PbSe Nanocrystal Assemblies:  Synthesis and Structural, Optical, and Electrical Characterization
Sashchiuk A., Amirav L., Bashouti M., Krueger M., Sivan U., Lifshitz E.
Nano Letters, 2003
15.
10.1016/j.mencom.2009.11.001_bib4_3
Gubin
Izv. Akad. Nauk, Ser. Khim., 2005
16.
Synthesis of CdSe/CdTe Nanobarbells
Halpert J.E., Porter V.J., Zimmer J.P., Bawendi M.G.
Journal of the American Chemical Society, 2006
17.
TEM-Induced Structural Evolution in Amorphous Fe Oxide Nanoparticles
Latham A.H., Wilson M.J., Schiffer P., Williams M.E.
Journal of the American Chemical Society, 2006
18.
G. M. Kosolapoff and L. Maier, Organic Phosphorus Compounds, Wiley-Interscience, New York, 1972, vol. 1.
19.
G. M. Kosolapoff and L. Maier, Organic Phosphorus Compounds, Wiley-Interscience, New York, 1972, vol. 3.
20.
THE SYNTHESIS OF ORGANOPHOSPHORUS COMPOUNDS DIRECTLY FROM THE ELEMENT
Brown C., Hudson R.F., Wartew G.A.
Phosphorous and Sulfur and the Related Elements, 1978
21.
New reactions involving the oxidative O-, N-, and C-phosphorylation of organic compounds by phosphorus and phosphides in the presence of metal complexes
Dorfman Y.A., Aleshkova M.M., Polimbetova G.S., Levina L.V., Petrova T.V., Abdreimova R.R., Doroshkevich D.M.
Russian Chemical Reviews, 1993
22.
Electrochemical syntheses based on elemental phosphorous and phosphorus acid esters
Tomilov A.P., Osadchenko I.M., Khudenko A.V.
Russian Chemical Reviews, 1996
23.
Organic chemistry of elemental phosphorus
Milyukov V.A., Budnikova Y.H., Sinyashin O.G.
Russian Chemical Reviews, 2005
24.
10.1016/j.mencom.2009.11.001_bib7_1
Trofimov
Izv. Akad. Nauk SSSR, Ser. Khim., 1988
25.
10.1016/j.mencom.2009.11.001_bib7_2
Gusarova
Izv. Akad. Nauk SSSR, Ser. Khim., 1989
26.
10.1016/j.mencom.2009.11.001_bib7_3
Malysheva
Izv. Akad. Nauk SSSR, Ser. Khim., 1989
27.
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
28.
10.1016/j.mencom.2009.11.001_bib8_2
Trofimov
Elem., 1991
29.
10.1016/j.mencom.2009.11.001_bib8_3
Trofimov
Main Group Chem. News, 1996
30.
10.1016/j.mencom.2009.11.001_bib8_4
Gusarova
Izv. Akad. Nauk, Ser. Khim., 1998
31.
10.1016/j.mencom.2009.11.001_bib9_1
Sukhov
Izv. Akad. Nauk, Ser. Khim., 2003
32.
S. F. Malysheva and S. N. Arbuzova, in Sovremennyi organicheskii sintez (Modern Organic Synthesis), ed. D. L. Rakhmankulov, Khimiya, Moscow, 2003, p. 160.(in Russian).
33.
Sukhov B., Malysheva S., Vakul’skaya T., Tirsky V., Martynovich E., Smetannikov Y., Tarasova N.
Arkivoc, 2003
34.
10.1016/j.mencom.2009.11.001_bib9_4
Trofimov
Kataliz v promyshlennosti, 2006
35.
M. M. Rauhut, Topics in Phosphorus Chemistry, Wiley-Interscience, New York, 1964, vol. 1.
36.
10.1016/j.mencom.2009.11.001_bib11_1
Bogolyubov
Zh. Obshch. Khim., 1966
37.
10.1016/j.mencom.2009.11.001_bib11_2
Bogolyubov
Dokl. Akad. Nauk SSSR, 1967
39.
10.1016/j.mencom.2009.11.001_bib13_1
Trofimov
Zh. Obshch. Khim., 1991
40.
10.1016/j.mencom.2009.11.001_bib13_2
Gusarova
Izv. Akad. Nauk, Ser. Khim., 1994
41.
10.1016/j.mencom.2009.11.001_bib13_3
Arbuzova
Zh. Obshch. Khim., 1996
43.
10.1016/j.mencom.2009.11.001_bib14_1
Gusarova
Zh. Obshch. Khim., 2002
44.
10.1016/j.mencom.2009.11.001_bib14_2
Gusarova
Izv. Akad. Nauk, Ser. Khim., 2003
45.
10.1016/j.mencom.2009.11.001_bib15_1
Trofimov
Zh. Obshch. Khim., 1990
46.
10.1016/j.mencom.2009.11.001_bib15_2
Gusarova
Zh. Obshch. Khim., 1993
47.
10.1016/j.mencom.2009.11.001_bib15_3
Trofimov
Zh. Obshch. Khim., 2000
48.
10.1016/j.mencom.2009.11.001_bib15_4
Gusarova
Khim. Geterotsikl. Soedin., 2001
49.
10.1016/j.mencom.2009.11.001_bib16_1
Gusarova
Zh. Obshch. Khim., 2005
50.
10.1016/j.mencom.2009.11.001_bib16_2
Malysheva
Zh. Obshch. Khim., 2007
51.
Phosphine in the synthesis of organophosphorus compounds
Trofimov B.A., Arbuzova S.N., Gusarova N.K.
Russian Chemical Reviews, 1999
54.
10.1016/j.mencom.2009.11.001_bib18_2
Gusarova
Zh. Obshch. Khim., 1997
55.
10.1016/j.mencom.2009.11.001_bib18_3
Trofimov
Zh. Obshch. Khim., 1997
56.
Gusarova N.K., Malysheva S.F., Kuimov V.A., Belogorlova N.A., Mikhailenko V.L., Trofimov B.A.
Mendeleev Communications, 2008
57.
10.1016/j.mencom.2009.11.001_bib19_1
Trofimov
Zh. Obshch. Khim., 1991
58.
10.1016/j.mencom.2009.11.001_bib19_2
Gusarova
Zh. Obshch. Khim., 1993
59.
Base-Catalyzed Addition of Phosphine to Aryl- and Hetarylethynes. An Efficient Method for the Preparation of 2-Substituted Trivinylphosphines
Trofimov B.A., Gusarova N.K., Arbuzova S.N., Malysheva S.F., Besten R.D., Brandsma L.
Synthesis, 1995
60.
10.1016/j.mencom.2009.11.001_bib19_4
Gusarova
Zh. Obshch. Khim., 2001
61.
10.1016/j.mencom.2009.11.001_bib20
Trofimov
Dokl. Akad. Nauk, 2009
62.
10.1016/j.mencom.2009.11.001_bib21_1
Gusarova
Zh. Obshch. Khim., 1990
63.
10.1016/j.mencom.2009.11.001_bib21_2
Gusarova
Zh. Org. Khim., 1996
64.
10.1016/j.mencom.2009.11.001_bib22
Trofimov
Zh. Obshch. Khim., 2005
65.
10.1016/j.mencom.2009.11.001_bib23
Shaikhudinova
Zh. Obshch. Khim., 2001
66.
10.1016/j.mencom.2009.11.001_bib24_1
Gusarova
Zh. Obshch. Khim., 2004
67.
10.1016/j.mencom.2009.11.001_bib24_2
Kuimov
Zh. Obshch. Khim., 2006
68.
TRIS[(5-CHLORO-2-THIENYL)METHYL] PHOSPHINE OXIDE FROM ELEMENTAL PHOSPHORUS AND 2-CHLORO-5-(CHLOROMETHYL) THIOPHENE
Gusarova N.K., Arbuzova S.N., Shaikhudinova S.I., Kazantseva T.I., Reutskaya A.M., Ivanova N.I., Papernaya L., Trofimov B.A.
Phosphorus, Sulfur and Silicon and the Related Elements, 2001
69.
10.1016/j.mencom.2009.11.001_bib26
Malysheva
Zh. Obshch. Khim., 1997
70.
10.1016/j.mencom.2009.11.001_bib27_1
Gusarova
Izv. Akad. Nauk, Ser. Khim., 2000
71.
10.1016/j.mencom.2009.11.001_bib27_2
Gusarova
Zh. Obshch. Khim., 2001
72.
Phosphorylation of Allyl Halides with White Phosphorus
Malysheva S., Sukhov B., Gusarova N., Shaikhudinova S., Kazantseva T., Belogorlova N., Kuimov V., Trofimov B.
Phosphorus, Sulfur and Silicon and the Related Elements, 2003
73.
10.1016/j.mencom.2009.11.001_bib29_1
Trofimov
Zh. Obshch. Khim., 1989
74.
10.1016/j.mencom.2009.11.001_bib29_2
Malysheva
Zh. Obshch. Khim., 2004
75.
10.1016/j.mencom.2009.11.001_bib30_1
Gusarova
Zh. Obshch. Khim., 2006
76.
10.1016/j.mencom.2009.11.001_bib30_2
Malysheva
Zh. Obshch. Khim., 2007
77.
10.1016/j.mencom.2009.11.001_bib31
Malysheva
Dokl. Akad. Nauk, 2008
78.
10.1016/j.mencom.2009.11.001_bib32
Gusarova
Zh. Obshch. Khim., 1995
79.
10.1016/j.mencom.2009.11.001_bib33
Gusarova
Zh. Obshch. Khim., 1990
80.
EFFICIENT ONE-POT PROCEDURES FOR THE PREPARATION OF SECONDARY PHOSPHINES
Brandsma L., Gusarova N.K., Gusarov A.V., Verkruijsse H.D., Trofimov B.A.
Synthetic Communications, 1994
82.
Brandsma L., van Doom J.A., de Lang R., Gusarova N.K., Trofimov B.A.
Mendeleev Communications, 1995
83.
10.1016/j.mencom.2009.11.001_bib34_4
Brandsma
Elem., 1997
84.
A Convenient Synthesis of Primary 2-Hydroxyorganophosphines from Red Phosphorus and Oxiranes
Arbuzova S.N., Brandsma L., Gusarova N.K., van der Kerk A.H., van Hooijdonk M.C., Trofimov B.A.
Synthesis, 2000
85.
10.1016/j.mencom.2009.11.001_bib35_1
Trofimov
Izv. Akad. Nauk, Ser. Khim., 1997
86.
10.1016/j.mencom.2009.11.001_bib35_2
Trofimov
Zh. Obshch. Khim., 1997
87.
Arbuzova S.N., Brandsma L., Gusarova N.K., Nikitin M.V., Trofimov B.A.
Mendeleev Communications, 2000
88.
10.1016/j.mencom.2009.11.001_bib36
Trofimov
Zh. Obshch. Khim., 2008
89.
10.1016/j.mencom.2009.11.001_bib37
Trofimov
Dokl. Akad. Nauk, 2009
90.
Addition of secondary phosphines to a vinyl ether of diacetone-D-glucose: a new approach to optically active phosphines and their derivatives
Trofimov B.A., Sukhov B.G., Malysheva S.F., Belogorlova N.A., Tantsirev A.P., Parshina L.N., Oparina L.A., Tunik S.P., Gusarova N.K.
Tetrahedron Letters, 2004
91.
Gusarova N.K., Ivanova N.I., Bogdanova M.V., Malysheva S.F., Belogorlova N.A., Sukhov B.G., Trofimov B.A.
Mendeleev Communications, 2004
92.
10.1016/j.mencom.2009.11.001_bib38_3
Gusarova
Synthesis, 2007
93.
Gusarova N.K., Malysheva S.F., Oparina L.A., Belogorlova N.A., Tantsyrev A.P., Parshina L.N., Sukhov B.G., Tlegenov R.T., Trofimov B.A.
Arkivoc, 2009
94.
B. A. Trofimov, S. F. Malysheva, N. A. Belogorlova, V. A. Kuimov, A. I. Albanov and N. K. Gusarova, Eur. J. Org. Chem., 2009, DOI:10.1002/ejoc.200900382.1.
95.
10.1016/j.mencom.2009.11.001_bib38_6
Trofimov
Synthesis, 2002
96.
10.1016/j.mencom.2009.11.001_bib38_7
Gusarova
Synthesis, 2008, 2008
97.
Addition of secondary phosphines to N-vinylpyrroles
Trofimov B.A., Malysheva S.F., Sukhov B.G., Belogorlova N.A., Schmidt E.Y., Sobenina L.N., Kuimov V.A., Gusarova N.K.
Tetrahedron Letters, 2003
98.
10.1016/j.mencom.2009.11.001_bib38_9
Gusarova
Synthesis, 2005
99.
10.1016/j.mencom.2009.11.001_bib39_1
Gusarova
Izv. Akad. Nauk, Ser. Khim., 2009
100.
Trofimov B.A., Malysheva S.F., Gusarova N.K., Belogorlova N.A., Vasilevsky S.F., Kobychev V.B., Sukhov B.G., Ushakov I.A.
Mendeleev Communications, 2007
101.
Stereoselective free-radical addition of secondary phosphine selenides to aromatic acetylenes
Trofimov B.A., Gusarova N.K., Arbuzova S.N., Ivanova N.I., Artem’ev A.V., Volkov P.A., Ushakov I.A., Malysheva S.F., Kuimov V.A.
Journal of Organometallic Chemistry, 2009
102.
Trofimov B.A., Arbuzova S.N., Mal’kina A.G., Gusarova N.K., Malysheva S.F., Nikitin M.V., Vakul'skaya T.I.
Mendeleev Communications, 1999
103.
Regio- and stereospecific addition of phosphines to cyanoacetylenes
Gusarova N.K., Shaikhudinova S.I., Arbuzova S.N., Vakul'skaya T.I., Sukhov B.G., Sinegovskaya L.M., Nikitin M.V., Mal'kina A.G., Chernysheva N.A., Trofimov B.A.
Tetrahedron, 2003
104.
Arbuzova S.N., Gusarova N.K., Bogdanova M.V., Ivanova N.I., Ushakov I.A., Mal’kina A.G., Trofimov B.A.
Mendeleev Communications, 2005
105.
Arbuzova S.N., Gusarova N.K., Bogdanova M.V., Ushakov I.A., Mal’kina A.G., Trofimov B.A.
Mendeleev Communications, 2007
106.
Base Catalyzed Double Addition of Secondary Phosphine Chalcogenides to Benzoylacetylene
Glotova T., Dvorko M.Y., Arbuzova S., Ushakov I., Verkhoturova S., Gusarova N., Trofimov B.
Letters in Organic Chemistry, 2007
107.
Chemo- and Regiospecific Monoaddition of Secondary Phosphine Sulfides to 1-Acyl-2-phenylacetylenes
Glotova T.E., Dvorko M.Y., Gusarova N.K., Arbuzova S.N., Ushakov I.A., Kazantseva T.I., Trofimov B.A.
Phosphorus, Sulfur and Silicon and the Related Elements, 2008
108.
Regioselective addition of secondary phosphine oxides to 3-(trialkylsilyl)- and 3-(trialkylgermyl)-2-propynals
Gusarova N.K., Reutskaya A.M., Ivanova N.I., Medvedeva A.S., Demina M.M., Novopashin P.S., Afonin A.V., Albanov A.I., Trofimov B.A.
Journal of Organometallic Chemistry, 2002
109.
10.1016/j.mencom.2009.11.001_bib40_2
Ivanova
Elem., 2004
110.
10.1016/j.mencom.2009.11.001_bib40_3
Gusarova
Synthesis, 2006
111.
10.1016/j.mencom.2009.11.001_bib41_1
Gusarova
Zh. Org. Khim., 2001
112.
10.1016/j.mencom.2009.11.001_bib41_2
Ivanova
Zh. Obshch. Khim., 2003
113.
10.1016/j.mencom.2009.11.001_bib42_1
Nindakova
Zh. Obshch. Khim., 2004
114.
10.1016/j.mencom.2009.11.001_bib42_2
Baikalova
Zh. Obshch. Khim., 2005
115.
10.1016/j.mencom.2009.11.001_bib42_3
Reznikov
Zh. Obshch. Khim., 2005
116.
10.1016/j.mencom.2009.11.001_bib42_4
Andreev
Izv. Akad. Nauk, Ser. Khim., 2007
117.
Catalytic oxidation of organic substrates with hydrogen peroxide in two-phase systems in the presence of peroxo-polyoxotungstates containing organic ligands
Pai Z.P., Berdnikova P.V., Tolstikov A.G., Roor O.N., Khlebnikova T.B., Gusarova N.K., Malysheva S.F., Ivanova N.I., Trofimov B.A.
Reaction Kinetics and Catalysis Letters, 2008
118.
10.1016/j.mencom.2009.11.001_bib43
Timoshenko
Khim. Tekhnologiya, 2008