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Fluoroalkylation of organic compounds

D Yu Mikhaylov 1
D Yu Mikhaylov
, 
1 A. E.  Arbuzov Institute of Organic and Physical Chemistry of Kazan Scientific Center of Russian Academy of Sciences
Published 30 November 2012
Communication , Volume 82, Issue 9, 835-864
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Mikhaylov D. Yu., Budnikova Y. H. Fluoroalkylation of organic compounds // Russian Chemical Reviews. 2013. Vol. 82. No. 9. pp. 835-864.
GOST all authors (up to 50)
Mikhaylov D. Yu., Budnikova Y. H. Fluoroalkylation of organic compounds // Russian Chemical Reviews. 2013. Vol. 82. No. 9. pp. 835-864.
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TY - JOUR
DO - 10.1070/RC2013v082n09ABEH004342
UR - https://rcr.colab.ws/publications/10.1070/RC2013v082n09ABEH004342
TI - Fluoroalkylation of organic compounds
T2 - Russian Chemical Reviews
AU - Mikhaylov, D Yu
AU - Budnikova, Yulia Hermanovna
PY - 2013
DA - 2012/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 835-864
IS - 9
VL - 82
ER -
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@article{2013_Mikhaylov,
author = {D Yu Mikhaylov and Yulia Hermanovna Budnikova},
title = {Fluoroalkylation of organic compounds},
journal = {Russian Chemical Reviews},
year = {2013},
volume = {82},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC2013v082n09ABEH004342},
number = {9},
pages = {835--864},
doi = {10.1070/RC2013v082n09ABEH004342}
}
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Cite this
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Mikhaylov, D. Yu., and Yulia Hermanovna Budnikova. “Fluoroalkylation of organic compounds.” Russian Chemical Reviews, vol. 82, no. 9, Nov. 2013, pp. 835-864. https://rcr.colab.ws/publications/10.1070/RC2013v082n09ABEH004342.
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Abstract

Data on fluoroalkylation and perfluoroalkylation methods in organic synthesis are analyzed, summarized and described systematically. The most practically important properties of compounds with fluoroalkyl substituents are illustrated. The key trends of the development and the potential of this field of organic chemistry are considered. Electrochemical syntheses of perfluoroalkyl derivatives that are inaccessible or experimentally difficult by regular chemical techniques are presented. Particular attention is paid to processes involving organometallic compounds as well as to prospects for the development of this field of research.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
2
A. A. Krasnovskii
Zhur. Fiz. Khim. , 1956
6.
Aromatic Trifluoromethylation with Metal Complexes
Tomashenko O.A., Grushin V.V.
Chemical Reviews , 2011
7.
Fluorine chemistry at the millennium
Dolbier W.R.
Journal of Fluorine Chemistry , 2005
9.
9
V. H. Lynch
Carnegie Inst. Year Book , 1954
10.
10
T. A. Kryukova
"Polyaro-graficheskii Analiz" (Polarographic Analysis) , 1959
12.
Fluorine in medicinal chemistry: A review of anti-cancer agents
Isanbor C., O’Hagan D.
Journal of Fluorine Chemistry , 2006
13.
Cho Y.S., Wu K.-., Moore M.A., Chou T.-., Danishefsky S.J.
Drugs of the Future , 2005
14.
Trifluoromethylation of Organic Compounds and Related Reactions
Kumadaki I., Ando A., Sato K., Tarui A., Omote M.
Synthesis , 2010
15.
Chirality-Sensing Supramolecular Systems
Hembury G.A., Borovkov V.V., Inoue Y.
Chemical Reviews , 2007
21.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
23.
Fluoroalkylation of aromatic compounds
Cowell A.B., Tamborski C.
Journal of Fluorine Chemistry , 1981
24.
Reactions of Atoms and Free Radicals in Solution. X. The Addition of Polyhalomethanes to Olefins
Kharasch M.S., Jensen E.V., Urry W.H.
Journal of the American Chemical Society , 1947
25.
Free Radical Additions Involving Fluorine Compounds. IV. The Addition of Dibromodifluoromethane to Some Fluoroölefins1
Tarrant P., Lovelace A.M., Lilyquist M.R.
Journal of the American Chemical Society , 1955
27.
One-step synthesis of epoxy(perfluoroalkyl)alkenes
Bazhin D.N., Gorbunova T.I., Zapevalov A.Y., Saloutin V.I.
Russian Journal of Organic Chemistry , 2009
30.
A new approach to the photochemical trifluoromethylation of aromatic compounds
Lai C., Mallouk T.E.
Journal of the Chemical Society Chemical Communications , 1993
31.
[60]- and [70]Fullerenes are trifluoromethylated across 5:6-bonds
Darwish A.D., Avent A.G., Abdul-Sada A.K., Taylor R.
Chemical Communications , 2003
34.
Perfluoroalkylation of aliphatic thiols in the presence of sodium hydroxymethanesulfinate
Anselmi E., Blazejewski J., Tordeux M., Wakselman C.
Journal of Fluorine Chemistry , 2000
37.
Electrochemical Oxy-trifluoromethylation of Butyl Acrylate
Sato Y., Watanabe S., Uneyama K.
Bulletin of the Chemical Society of Japan , 1993
38.
Electrochemical Hydrotrifluoromethylation of Dialkyl Fumarates
Dan-oh Y., Uneyama K.
Bulletin of the Chemical Society of Japan , 1995
40.
Electrochemical trifluoromethylation of aromatic compounds
Grinberg V.A., Lundgren S.A., Sterlin S.R., Mysov E.I.
Russian Chemical Bulletin , 1997
41.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1950
44.
Radical Reactions in Aqueous Medium Using (Me3Si)3SiH
Postigo A., Kopsov S., Ferreri C., Chatgilialoglu C.
Organic Letters , 2007
46.
Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis.
Nagib D.A., Scott M.E., MacMillan D.W.
Journal of the American Chemical Society , 2009
48.
Direct Functionalization of Polycyclic Aromatics via Radical Perfluoroalkylation
Li Y., Li C., Yue W., Jiang W., Kopecek R., Qu J., Wang Z.
Organic Letters , 2010
49.
Light-induced iodoperfluoroalkylation reactions of carbon–carbon multiple bonds in water
Slodowicz M., Barata-Vallejo S., Vázquez A., Nudelman N.S., Postigo A.
Journal of Fluorine Chemistry , 2012
50.
Cascade Radical Reaction Induced by Polarity-Mismatched Perfluoroalkylation
51.
High-temperature and photochemical syntheses of C60 and C70 fullerene derivatives with linear perfluoroalkyl chains
Shustova N.B., Kareev I.E., Kuvychko I.V., Whitaker J.B., Lebedkin S.F., Popov A.A., Dunsch L., Chen Y., Seppelt K., Strauss S.H., Boltalina O.V.
Journal of Fluorine Chemistry , 2010
52.
The Chemistry of Highly Fluorinated Carbocations
Krespan C.G., Petrov V.A.
Chemical Reviews , 1996
54.
Existence of the Halocarbonyl and Trifluoromethyl Cations in the Condensed Phase
Christe K.O., Hoge B., Boatz J.A., Prakash G.K., Olah G.A., Sheehy J.A.
Inorganic Chemistry , 1999
55.
Electrophilic Perfluoroalkylating Agents.
56.
A New Method of Perfluoroalkylation
YAGUPOLSKII L.M., MALETINA I.I., KONDRATENKO N.V., ORDA V.V.
Synthesis , 1978
57.
Aromatic compounds with new fluorine-containing substituents
58.
Novel 10-I-3 Hypervalent Iodine-Based Compounds for Electrophilic Trifluoromethylation
Eisenberger P., Gischig S., Togni A.
Chemistry - A European Journal , 2006
62.
Reactivity of a 10-I-3 Hypervalent Iodine Trifluoromethylation Reagent With Phenols
Stanek K., Koller R., Togni A.
Journal of Organic Chemistry , 2008
63.
Zinc-Mediated Formation of Trifluoromethyl Ethers from Alcohols and Hypervalent Iodine Trifluoromethylation Reagents
Koller R., Stanek K., Stolz D., Aardoom R., Niedermann K., Togni A.
Angewandte Chemie - International Edition , 2009
64.
A Ritter-Type Reaction: Direct Electrophilic Trifluoromethylation at Nitrogen Atoms Using Hypervalent Iodine Reagents
Niedermann K., Früh N., Vinogradova E., Wiehn M.S., Moreno A., Togni A.
Angewandte Chemie - International Edition , 2010
66.
Electrophilic Trifluoromethylation of S-Hydrogen Phosphorothioates
Santschi N., Togni A.
Journal of Organic Chemistry , 2011
67.
67
N. N. Mel'nikov
Zhur. Obshch. Khim. , 1940
68.
Probing the interactions of an acyl carrier protein domain from the 6-deoxyerythronolide B synthase
Charkoudian L.K., Liu C.W., Capone S., Kapur S., Cane D.E., Togni A., Seebach D., Khosla C.
Protein Science , 2011
73.
NMR-Solution Structures and Affinities for the Human Somatostatin G-Protein-Coupled Receptors hsst1–5 of CF3 Derivatives of Sandostatin® (Octreotide)
Seebach D., Widmer H., Capone S., Ernst R., Bremi T., Kieltsch I., Togni A., Monna D., Langenegger D., Hoyer D.
Helvetica Chimica Acta , 2009
74.
Acid-mediated formation of trifluoromethyl sulfonates from sulfonic acids and a hypervalent iodine trifluoromethylating agent
77.
Highly Selective Trifluoromethylation of 1,3-Disubstituted Arenes through Iridium-Catalyzed Arene Borylation
78.
Copper-Catalyzed C(sp3)–C(sp3) Bond Formation Using a Hypervalent Iodine Reagent: An Efficient Allylic Trifluoromethylation
Wang X., Ye Y., Zhang S., Feng J., Xu Y., Zhang Y., Wang J.
Journal of the American Chemical Society , 2011
79.
Copper-Catalyzed Trifluoromethylation of Unactivated Olefins
Parsons A.T., Buchwald S.L.
Angewandte Chemie - International Edition , 2011
81.
Direct C2-trifluoromethylation of indole derivatives catalyzed by copper acetate
Shimizu R., Egami H., Nagi T., Chae J., Hamashima Y., Sodeoka M.
Tetrahedron Letters , 2010
84.
Pd(II)-catalyzed ortho-trifluoromethylation of arenes using TFA as a promoter.
Wang X., Truesdale L., Yu J.
Journal of the American Chemical Society , 2010
86.
N-Trihalomethyl derivatives of benzimidazole, benzotriazole and indazole
Yagupolskii L.M., Fedyuk D.V., Petko K.I., Troitskaya V.I., Rudyk V.I., Rudyuk V.V.
Journal of Fluorine Chemistry , 2000
87.
Direct Electrophilic N-Trifluoromethylation of Azoles by a Hypervalent Iodine Reagent
Niedermann K., Früh N., Senn R., Czarniecki B., Verel R., Togni A.
Angewandte Chemie - International Edition , 2012
88.
The New Age of Electrophilic Perfluoro­alk­ylation Reactions†‡
Macé Y., Magnier E.
European Journal of Organic Chemistry , 2012
89.
89
A. A. Krasnovskii
Izd. Akad. Nauk SSSR, Moscow , 1955
91.
Synthesis of Trifluoromethyl-Porphyrins and -Chlorins
Tamiaki H., Nagata Y., Tsudzuki S.
European Journal of Organic Chemistry , 1999
93.
Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective
Shibata N., Matsnev A., Cahard D.
Beilstein Journal of Organic Chemistry , 2010
96.
96
L. M. Vorob'eva
Biokhimiya , 1958
97.
Fluorinated Carbanions
Farnham W.B.
Chemical Reviews , 1996
98.
98
W. Franke
Chem. Zentr. , 1954
101.
Coupling of fluoroform with aldehydes using an electrogenerated base
Barhdadi R., Troupel M., Périchon J.
Chemical Communications , 1998
102.
Fluoroform: an efficient precursor for the trifluoromethylation of aldehydes
Folléas B., Marek I., Normant J., Saint-Jalmes L.
Tetrahedron , 2000
107.
Synthesis of Optically Pure Perfluoroalkyl Aryl Carbinols
Solladié-Cavallo A., Suffert J.
Synthesis , 1985
108.
108
F. Fichter
Helv. Chim. Acta , 1924
109.
Perfluoroalkylation in flow microreactors: generation of perfluoroalkyllithiums in the presence and absence of electrophiles
Nagaki A., Tokuoka S., Yamada S., Tomida Y., Oshiro K., Amii H., Yoshida J.
Organic and Biomolecular Chemistry , 2011
110.
Synthesis and reactions of perfluoro-n-octylmagnesium bromide
Smith C.F., Soloski E.J., Tamborski C.
Journal of Fluorine Chemistry , 1974
111.
Some perfluoroalkyl grignard reagents and their derivatives
Dua S.S., Howells R.D., Gilman H.
Journal of Fluorine Chemistry , 1974
112.
Group IIB metal alkyls: the synthesis of trifluorosilyl and trifluoromethyl alkyls of cadmium and zinc
Guerra M.A., Bierschenk T.R., Lagow R.J.
Journal of the American Chemical Society , 1986
113.
Preparation and properties of ZnBr(CF3)·2L — a convenient route for the preparation of CF3I
Naumann D., Tyrra W., Kock B., Rudolph W., Wilkes B.
Journal of Fluorine Chemistry , 1994
116.
Ultrasound-promoted selective perfluoroalkylation on the desired position of organic molecules
Kitazume T., Ishikawa N.
Journal of the American Chemical Society , 1985
126.
Novel Nucleophilic Trifluoromethylation of Vicinal Diol Cyclic Sulfates
Takechi N., Ait-Mohand S., Medebielle M., Dolbier W.R.
Organic Letters , 2002
127.
A New and Efficient Method for the Synthesis of Trifluoromethylthio- and Selenoethers
128.
Nucleophilic Perfluoroalkylation of Aldehydes, Ketones, Imines, Disulfides, and Diselenides
Pooput C., Dolbier, W.R., Médebielle M.
Journal of Organic Chemistry , 2006
129.
Perfluoroalkylation with Organosilicon Reagents
Prakash G.K., Yudin A.K.
Chemical Reviews , 1997
131.
Die ersten CF3-substituierten organyl(chlor)silane
Ruppert I., Schlich K., Volbach W.
Tetrahedron Letters , 1984
137.
Synthesis, structure and reactivity of a trifluoromethyl sulfide anionic salt stabilized with tetrakis(dimethylamino)ethylene dication (TDAE2+)
Kolomeitsev A., Médebielle M., Kirsch P., Lork E., Röschenthaler G.
Journal of the Chemical Society Perkin Transactions 1 , 2000
138.
Regioselective 1,4-trifluoromethylation of α,β-enones using ‘protect-in-situ’ methodology
Sevenard D.V., Sosnovskikh V.Y., Kolomeitsev A.A., Königsmann M.H., Röschenthaler G.
Tetrahedron Letters , 2003
141.
Anhydrodihydroartemisinin and Its 10-Trifluoromethyl Analogue:  Access to Novel D-Ring-Contracted Artemisinin Trifluoromethyl Ketones
Grellepois F., Chorki F., Crousse B., Ourévitch M., Bonnet-Delpon D., Bégué J.
Journal of Organic Chemistry , 2002
143.
Nucleophilic difluoromethylation of CN bonds in heterocycles with difluoromethyl silane reagents
144.
Reactions of Sulfur- and Phosphorus-Substituted Fluoroalkylating Silicon Reagents with Imines and Enamines under Acidic Conditions
Kosobokov M.D., Dilman A.D., Struchkova M.I., Belyakov P.A., Hu J.
Journal of Organic Chemistry , 2012
145.
Difluoro(trimethylsilyl)acetonitrile: Synthesis and Fluoroalkylation Reactions
Kosobokov M.D., Dilman A.D., Levin V.V., Struchkova M.I.
Journal of Organic Chemistry , 2012
146.
Trifluoromethylation of aryl and heteroaryl halides
Roy S., Gregg B.T., Gribble G.W., Le V., Roy S.
Tetrahedron , 2011
147.
α-Fluoroalkylation of carbonyl compounds mediated by a highly reactive alkyl-rhodium complex
Sato K., Yamazoe S., Akashi Y., Hamano T., Miyamoto A., Sugiyama S., Tarui A., Omote M., Kumadaki I., Ando A.
Journal of Fluorine Chemistry , 2010
150.
Organic Synthesis—Where now?
Seebach D.
Angewandte Chemie - International Edition , 1990
151.
151
V. M. Rodionov
Zhur. Obshch. Khim. , 1936
155.
623. Organometallic fluorine compounds. Part I. The synthesis of trifluoromethyl and pentafluoroethyl mercurials
156.
624. Organometallic fluorine compounds. Part II. The synthesis of bistrifluoromethylmercury
Emeléus H.J., Haszeldine R.N.
Journal of the Chemical Society (Resumed) , 1949
161.
10.1021/ja038527+
162.
Synthesis of the First Family of Rhodium(I) Perfluoroalkyl Complexes from Rhodium(I) Fluoro Complexes1
Vicente J., Gil-Rubio J., Guerrero-Leal J., Bautista D.
Organometallics , 2004
163.
Bis(Trifluoromethyl)Mercury
Eujen R., Gomes G., Morrison J.A.
Inorganic Syntheses , 1986
164.
Active Trifluoromethylating Agents from Well-Defined Copper(I)−CF3 Complexes
Dubinina G.G., Furutachi H., Vicic D.A.
Journal of the American Chemical Society , 2008
165.
Perfluoroalkyl complexes of palladium and platinum
Rosevear D.T., Stone F.G.
Journal of the Chemical Society A Inorganic Physical Theoretical , 1968
166.
Synthesen und Charakterisierungen der ersten Tris- und Tetrakis(trifluormethyl)palladate(II) und -platinate(II), [M(CF3)3(PPh3)]— und [M(CF3)4]2— (M = Pd, Pt)
Naumann D., Kirij N.V., Maggiarosa N., Tyrra W., Yagupolskii Y.L., Wickleder M.S.
Zeitschrift fur Anorganische und Allgemeine Chemie , 2004
168.
Notes
McBride D.W., Stafford S.L., Stone F.G., Heinekey D.M., Millar I.T., Mann F.G., Finch A., Gardner P.J., Lockhart J.C., Bhati A., Gladych J.M., Brown R.N., Winter G., Tobia S.K., Milad N.E., et. al.
Journal of the Chemical Society (Resumed) , 1963
169.
341. Chemistry of the metal carbonyls. Part XXV. Flurocarbon derivatives of nickel
McBride D.W., Dudek E., Stone F.G.
Journal of the Chemical Society (Resumed) , 1964
170.
Reactions of low-valent metal complexes with fluorocarbons. Part VII. Bis(triphenylphosphine)(π-ethylene)nickel and tetrakis(methyldiphenylphosphine)nickel
172.
Tetrakis(triethylphosphine)nickel(0) and related complexes
174.
Transformations of F-Alkyl Iodides and Bromides Induced by Nickel(0) Carbonyl
Krespan C.G., Dixon D.A.
Journal of Organic Chemistry , 1998
176.
Exploring Trifluoromethylation Reactions at Nickel: A Structural and Reactivity Study
Dubinina G.G., Brennessel W.W., Miller J.L., Vicic D.A.
Organometallics , 2008
177.
Unexpected H2O-Induced Ar−X Activation with Trifluoromethylpalladium(II) Aryls
Grushin V.V., Marshall W.J.
Journal of the American Chemical Society , 2006
178.
Methyl fluorosulphonyldifluoroacetate; a new trifluoromethylating agent
Chen Q., Wu S.
Journal of the Chemical Society Chemical Communications , 1989
179.
Aromatic trifluoromethylation catalytic in copper.
Oishi M., Kondo H., Amii H.
Chemical Communications , 2009
180.
Magnitudes of Electron-Withdrawing Effects of the Trifluoromethyl Ligand in Organometallic Complexes of Copper and Nickel
Kieltsch I., Dubinina G.G., Hamacher C., Kaiser A., Torres-Nieto J., Hutchison J.M., Klein A., Budnikova Y., Vicic D.A.
Organometallics , 2010
181.
181
Chem. Abs. , 1947
183.
Tetrakis{3,5-bis(perfluorohexyl)phenyl}borate: a highly fluorous anion
van den Broeke J., Deelman B., van Koten G.
Tetrahedron Letters , 2001
184.
Phosphorous(III) compounds incorporating perfluoroalkyl-derivatised biphenolic units
Adams D.J., Gudmunsen D., Hope E.G., Stuart A.M., West A.
Journal of Fluorine Chemistry , 2003
189.
Palladium-Catalyzed C–H Perfluoroalkylation of Arenes
Loy R.N., Sanford M.S.
Organic Letters , 2011
190.
The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides
Cho E.J., Senecal T.D., Kinzel T., Zhang Y., Watson D.A., Buchwald S.L.
Science , 2010
191.
Electrochemistry within molecules using ultrafast cyclic voltammetry
Amatore C., Bouret Y., Maisonhaute E., Abruña H.D., Goldsmith J.I.
Comptes Rendus Chimie , 2003
193.
Trends in organic electrosynthesis
Utley J.
Chemical Society Reviews , 1997
196.
Metal complex catalysis in organic electrosynthesis
198.
Metal complexes with non-innocent ligands
Butin K.P., Beloglazkina E.K., Zyk N.V.
Russian Chemical Reviews , 2005
199.
199
Yu. K. Delimarskii
Byull. Izobr. , 1970
202.
Highly reactive σ-organonickel complexes in electrocatalytic processes
Budnikova Y.H., Perichon J., Yakhvarov D.G., Kargin Y.M., Sinyashin O.G.
Journal of Organometallic Chemistry , 2001
203.
Electrocatalytic fluoroalkylation of olefins
Mikhaylov D.Y., Budnikova Y.H., Gryaznova T.V., Krivolapov D.V., Litvinov I.A., Vicic D.A., Sinyashin O.G.
Journal of Organometallic Chemistry , 2009
204.
Electrocatalytic Fluoroalkylation of Olefins
Mikhaylov D.Y., Budnikova Y.H., Gryaznova T., Sinyashin O.G.
ECS Transactions , 2010
205.
Nanocluster Catalysts in Electrochemical Transformations with Formation and Break of P- and C- Bonds
Budnikova Y.H., Mikhaylov D.Y., Gryaznova T., Sinyashin O.G.
ECS Transactions , 2010
206.
Electrocatalytic fluoroalkylation of olefins
Mikhaylov D.Y., Gryaznova T.V., Budnikova Y.G., Sinyashin O.G.
Russian Chemical Bulletin , 2010
207.
207
F. Fichter
"Organische Elektrochemie" , 1942
208.
208
O. A. Reutov
"Teoreticheskie Problemy Organicheskoi Khimii" (Theoretical Problems in Organic Chemistry) , 1956
209.
Indirect electroreductive radical cyclization of halogeno ethers using nickel(II) complexes as electron-transfer catalysts
Ozaki S., Matsushita H., Ohmori H.
Journal of the Chemical Society Chemical Communications , 1992
211.
211
C. Schall
Z. Elektrochem. , 1923
212.
212
L. V. Pavlova
Zh. Obshch. Khim. , 1965
213.
213
F. Yu. Rachinskii
"Khimiya Seraorganicheskikh Soedinenii, Soderzhashchikh-sya v Neftyakh i Nefteproduktakh" (Chemistry of Organo-sulphur Compounds Present in Petroleum and Petroleum Products) , 1966
214.
214
L. V. Pavlova
1965
215.
Aromatic perfluoroalkylation with metal complexes in electrocatalytic conditions
Khrizanforov M., Gryaznova T., Sinyashin O., Budnikova Y.
Journal of Organometallic Chemistry , 2012
217.
Synthesis and characterization of chromium and molybdenum(0) complexes bearing the (pentafluoroethyl)diphenylphosphine (pfepp) ligand
Palcic J.D., Baughman R.G., Golynskiy M.V., Frawley S.B., Peters R.G.
Journal of Organometallic Chemistry , 2005
219.
Phosphorus(III) ligands with fluorous ponytails
Bhattacharyya P., Gudmunsen D., Hope E.G., Kemmitt R.D., Paige D.R., Stuart A.M.
Journal of the Chemical Society Perkin Transactions 1 , 1997
222.
222
Chem. Abs. , 1961
223.
Organic chemistry of elemental phosphorus
Milyukov V.A., Budnikova Y.H., Sinyashin O.G.
Russian Chemical Reviews , 2005
224.
Electrochemical synthesis of organophosphorus compounds with PO, PN and PC bonds from white phosphorus
Kargin Y.M., Budnikova Y.H., Martynov B.I., Turygin V.V., Tomilov A.P.
Journal of Electroanalytical Chemistry , 2001
225.
Novel electrochemical pathway to fluoroalkyl phosphines and phosphine oxides
Mikhaylov D.Y., Gryaznova T.V., Dudkina Y.B., Polyancev F.M., Latypov S.K., Sinyashin O.G., Budnikova Y.H.
Journal of Fluorine Chemistry , 2013
226.
Novel Perfluoroalkyl-Diphenylphosphine Compounds. Syntheses and Reaction Mechanisms
227.
MII/MIII-Catalyzed ortho-Fluoroalkylation of 2-Phenylpyridine
Dudkina Y.B., Mikhaylov D.Y., Gryaznova T.V., Sinyashin O.G., Vicic D.A., Budnikova Y.H.
European Journal of Organic Chemistry , 2012
228.
Decarboxylative trifluoromethylation of aryl halides using well-defined copper–trifluoroacetate and –chlorodifluoroacetate precursors
McReynolds K.A., Lewis R.S., Ackerman L.K., Dubinina G.G., Brennessel W.W., Vicic D.A.
Journal of Fluorine Chemistry , 2010