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Phosphorylation of C--H bonds of aromatic compounds using metals and metal complexes

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1 A. E. Arbuzov Institute of Organic and Physical Chemistry of Kazan Scientific Center of Russian Academy of Sciences
Published 30 November 2014
Communication , Volume 84, Issue 9, 917-951
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Budnikova Y. H., Sinyashin O. G. Phosphorylation of C--H bonds of aromatic compounds using metals and metal complexes // Russian Chemical Reviews. 2015. Vol. 84. No. 9. pp. 917-951.
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Budnikova Y. H., Sinyashin O. G. Phosphorylation of C--H bonds of aromatic compounds using metals and metal complexes // Russian Chemical Reviews. 2015. Vol. 84. No. 9. pp. 917-951.
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TY - JOUR
DO - 10.1070/RCR4525
UR - https://rcr.colab.ws/publications/10.1070/RCR4525
TI - Phosphorylation of C--H bonds of aromatic compounds using metals and metal complexes
T2 - Russian Chemical Reviews
AU - Budnikova, Yulia Hermanovna
AU - Sinyashin, Oleg Gerol'dovich
PY - 2015
DA - 2014/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 917-951
IS - 9
VL - 84
ER -
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@article{2015_Budnikova,
author = {Yulia Hermanovna Budnikova and Oleg Gerol'dovich Sinyashin},
title = {Phosphorylation of C--H bonds of aromatic compounds using metals and metal complexes},
journal = {Russian Chemical Reviews},
year = {2015},
volume = {84},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4525},
number = {9},
pages = {917--951},
doi = {10.1070/RCR4525}
}
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Cite this
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Budnikova, Yulia Hermanovna, and Oleg Gerol'dovich Sinyashin. “Phosphorylation of C--H bonds of aromatic compounds using metals and metal complexes.” Russian Chemical Reviews, vol. 84, no. 9, Nov. 2015, pp. 917-951. https://rcr.colab.ws/publications/10.1070/RCR4525.
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Abstract

Key achievements and current trends in the development of methods for phosphorylation of aromatic C--H bonds catalyzed by metal salts and complexes are considered. The most important and promising approaches of the last decade, including those concerning the synthesis and properties of arylphosphonates, are distinguished. Methods for the introduction of a phosphonate group into non-activated and functionally substituted aromatic compounds and heteroaromatic molecules and phosphorylation--cyclization reactions involving acetylenes, 2-isocyanobiphenyls and alkynoates are analyzed. The possibilities of ligand-directed phosphorylation of compounds with aromatic C--H bonds and presumed mechanisms and intermediates in the C--P bond formation reactions are considered. The potential of this extensively developing research trend in organic and organoelement chemistry is highlighted.

The bibliography includes 263~references.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
2.
Corbridge D.E.
2016
3.
3
M. F. Shostakovskii
"Prostye Vinilovye Efiry" (Vinyl Ethers) , 1952
4.
4
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1949
7.
Identification of triazinoindol-benzimidazolones as nanomolar inhibitors of the Mycobacterium tuberculosis enzyme TDP-6-deoxy-d-xylo-4-hexopyranosid-4-ulose 3,5-epimerase (RmlC)
Sivendran S., Jones V., Sun D., Wang Y., Grzegorzewicz A.E., Scherman M.S., Napper A.D., McCammon J.A., Lee R.E., Diamond S.L., McNeil M.
Bioorganic and Medicinal Chemistry , 2010
8.
Discovery of a Series of Phosphonic Acid-Containing Thiazoles and Orally Bioavailable Diamide Prodrugs That Lower Glucose in Diabetic Animals Through Inhibition of Fructose-1,6-Bisphosphatase
Dang Q., Liu Y., Cashion D.K., Kasibhatla S.R., Jiang T., Taplin F., Jacintho J.D., Li H., Sun Z., Fan Y., DaRe J., Tian F., Li W., Gibson T., Lemus R., et. al.
Journal of Medicinal Chemistry , 2010
9.
Structure-Guided Design, Synthesis, and Evaluation of Guanine-Derived Inhibitors of the eIF4E mRNA–Cap Interaction
Chen X., Kopecky D.J., Mihalic J., Jeffries S., Min X., Heath J., Deignan J., Lai S., Fu Z., Guimaraes C., Shen S., Li S., Johnstone S., Thibault S., Xu H., et. al.
Journal of Medicinal Chemistry , 2012
10.
Synthesis of a diverse series of phosphacoumarins with biological activity.
Li X., Zhang D., Pang H., Shen F., Fu H., Jiang Y., Zhao Y.
Organic Letters , 2005
12.
Intermediate temperature proton conductors for PEM fuel cells based on phosphonic acid as protogenic group: A progress report
Steininger H., Schuster M., Kreuer K.D., Kaltbeitzel A., Bingöl B., Meyer W.H., Schauff S., Brunklaus G., Maier J., Spiess H.W.
Physical Chemistry Chemical Physics , 2007
13.
Tin(iv) phosphonates: porous nanoparticles and pillared materials
Kirumakki S., Huang J., Subbiah A., Yao J., Rowland A., Smith B., Mukherjee A., Samarajeewa S., Clearfield A.
Journal of Materials Chemistry A , 2009
14.
Functionalization of Oxide Surfaces by Terpyridine Phosphonate Ligands: Surface Reactions and Anchoring Geometry
Spampinato V., Tuccitto N., Quici S., Calabrese V., Marletta G., Torrisi A., Licciardello A.
Langmuir , 2010
15.
Palladacycle-catalyzed phosphonation of aryl halides in neat water
Xu K., Yang F., Zhang G., Wu Y.
Green Chemistry , 2013
16.
Recent Advances in Metal-Catalyzed C–P Bond Formation
Glueck D.S.
Topics in Organometallic Chemistry , 2010
17.
Review on Modern Advances of Chemical Methods for the Introduction of a Phosphonic Acid Group
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
19.
19
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1959
20.
Review: Organophosphonates: occurrence, synthesis and biodegradation by microorganisms
G.Ternan N., Mc Grath J.W., Mc Mullan G., Quinn J.P.
World Journal of Microbiology and Biotechnology , 1998
22.
Fructose-1,6-bisphosphatase Inhibitors. 2. Design, Synthesis, and Structure−Activity Relationship of a Series of Phosphonic Acid Containing Benzimidazoles that Function as 5′-Adenosinemonophosphate (AMP) Mimics
Dang Q., Kasibhatla S.R., Xiao W., Liu Y., DaRe J., Taplin F., Reddy K.R., Scarlato G.R., Gibson T., van Poelje P.D., Potter S.C., Erion M.D.
Journal of Medicinal Chemistry , 2009
24.
α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Antagonists: From Bench to Bedside
Mattes H., Carcache D., Kalkman H.O., Koller M.
Journal of Medicinal Chemistry , 2010
25.
Discovery of Potent, Selective, Orally Active, Nonpeptide Inhibitors of Human Mast Cell Chymase
Greco M.N., Hawkins M.J., Powell E.T., Almond, H.R., de Garavilla L., Hall J., Minor L.K., Wang Y., Corcoran T.W., Di Cera E., Cantwell A.M., Savvides S.N., Damiano B.P., Maryanoff B.E., et. al.
Journal of Medicinal Chemistry , 2007
26.
Mercaptophosphonate Compounds as Broad-Spectrum Inhibitors of the Metallo-β-lactamases
Lassaux P., Hamel M., Gulea M., Delbrück H., Mercuri P.S., Horsfall L., Dehareng D., Kupper M., Frère J., Hoffmann K., Galleni M., Bebrone C.
Journal of Medicinal Chemistry , 2010
27.
Structure−Activity Relationship of (N)-Methanocarba Phosphonate Analogues of 5′-AMP as Cardioprotective Agents Acting Through a Cardiac P2X Receptor
Kumar T.S., Zhou S., Joshi B.V., Balasubramanian R., Yang T., Liang B.T., Jacobson K.A.
Journal of Medicinal Chemistry , 2010
28.
Examination of Phosphoryl-Mimicking Functionalities within a Macrocyclic Grb2 SH2 Domain-Binding Platform
Kang S., Shi Z., Worthy K.M., Bindu L.K., Dharmawardana P.G., Choyke S.J., Bottaro D.P., Fisher R.J., Burke T.R.
Journal of Medicinal Chemistry , 2005
29.
Drugs in development: bisphosphonates and metalloproteinase inhibitors
Catterall J.B., Cawston T.E.
Arthritis Research , 2003
30.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
31.
Synthesis of α-substituted fosmidomycin analogues as highly potent Plasmodium falciparum growth inhibitors
Haemers T., Wiesner J., Poecke S.V., Goeman J., Henschker D., Beck E., Jomaa H., Calenbergh S.V.
Bioorganic and Medicinal Chemistry Letters , 2006
35.
Prodrugs of Phosphates and Phosphonates
Hecker S.J., Erion M.D.
Journal of Medicinal Chemistry , 2008
36.
Discovery of Phosphonic Diamide Prodrugs and Their Use for the Oral Delivery of a Series of Fructose 1,6-Bisphosphatase Inhibitors
Dang Q., Kasibhatla S.R., Jiang T., Fan K., Liu Y., Taplin F., Schulz W., Cashion D.K., Reddy K.R., van Poelje P.D., Fujitaki J.M., Potter S.C., Erion M.D.
Journal of Medicinal Chemistry , 2008
38.
Selective Functionalization of P4by Metal-Mediated CP Bond Formation
Heinl S., Reisinger S., Schwarzmaier C., Bodensteiner M., Scheer M.
Angewandte Chemie - International Edition , 2014
40.
Direct Phosphonylation of Aromatic Azaheterocycles
Van der Jeught S., Stevens C.V.
Chemical Reviews , 2009
41.
41
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1950
43.
A Novel Synthesis of Dialkyl Arenephosphonates
Hirao T., Masunaga T., Ohshiro Y., Agawa T.
Synthesis , 1981
46.
Palladium-Catalyzed Cross-Coupling ofH-Phosphinate Esters with Chloroarenes
47.
Ni(II)/Zn catalyzed reductive coupling of aryl halides with diphenylphosphine oxide in water.
Zhang X., Liu H., Hu X., Tang G., Zhu J., Zhao Y.
Organic Letters , 2011
48.
Synthesis of Water-Soluble Phosphine Oxides by Pd/C-Catalyzed P–C Coupling in Water
Rummelt S.M., Ranocchiari M., van Bokhoven J.A.
Organic Letters , 2012
50.
Homolytic substitution at phosphorus for the synthesis of alkyl and aryl phosphanes.
Vaillard S., Mück-Lichtenfeld C., Grimme S., Studer A.
Angewandte Chemie - International Edition , 2007
51.
Memory of axial chirality in aryl radical phosphanylations.
Bruch A., Ambrosius A., Fröhlich R., Studer A., Guthrie D.B., Zhang H., Curran D.P.
Journal of the American Chemical Society , 2010
55.
Microwave-Promoted Palladium(II)-Catalyzed CP Bond Formation by Using Arylboronic Acids or Aryltrifluoroborates
Andaloussi M., Lindh J., Sävmarker J., J. R. Sjöberg P., Larhed M.
Chemistry - A European Journal , 2009
56.
Nickel-Catalyzed C–P Cross-Coupling of Arylboronic Acids with P(O)H Compounds
Hu G., Chen W., Fu T., Peng Z., Qiao H., Gao Y., Zhao Y.
Organic Letters , 2013
58.
Metal-catalyzed synthesis of hetero-substituted alkenes and alkynes
Evano G., Gaumont A., Alayrac C., Wrona I.E., Giguere J.R., Delacroix O., Bayle A., Jouvin K., Theunissen C., Gatignol J., Silvanus A.C.
Tetrahedron , 2014
59.
Key green chemistry research areas—a perspective from pharmaceutical manufacturers
Constable D.J., Dunn P.J., Hayler J.D., Humphrey G.R., Leazer, Jr. J.L., Linderman R.J., Lorenz K., Manley J., Pearlman B.A., Wells A., Zaks A., Zhang T.Y.
Green Chemistry , 2007
61.
61
A. N. Terenin
1959
62.
Palladium- and Copper-Catalyzed Arylation of Carbon−Hydrogen Bonds
Daugulis O., Do H., Shabashov D.
Accounts of Chemical Research , 2009
63.
Transition metal-catalyzed C–H activation reactions: diastereoselectivity and enantioselectivity
Giri R., Shi B., Engle K.M., Maugel N., Yu J.
Chemical Society Reviews , 2009
64.
Rhodium-Catalyzed C−C Bond Formation via Heteroatom-Directed C−H Bond Activation
65.
C−H Activation for the Construction of C−B Bonds
Mkhalid I.A., Barnard J.H., Marder T.B., Murphy J.M., Hartwig J.F.
Chemical Reviews , 2009
68.
If CH Bonds Could Talk: Selective CH Bond Oxidation
Newhouse T., Baran P.S.
Angewandte Chemie - International Edition , 2011
71.
Direct C−H Transformation via Iron Catalysis
Sun C., Li B., Shi Z.
Chemical Reviews , 2010
73.
C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.
Yamaguchi J., Yamaguchi A.D., Itami K.
Angewandte Chemie - International Edition , 2012
74.
Beyond directing groups: transition-metal-catalyzed C-H activation of simple arenes.
Kuhl N., Hopkinson M.N., Wencel-Delord J., Glorius F.
Angewandte Chemie - International Edition , 2012
75.
Ruthenium(II)-Catalyzed C–H Bond Activation and Functionalization
Arockiam P.B., Bruneau C., Dixneuf P.H.
Chemical Reviews , 2012
76.
Organopalladium(IV) chemistry.
Xu L., Li B., Yang Z., Shi Z.
Chemical Society Reviews , 2010
78.
Palladium(II)-Catalyzed CH Activation/CC Cross-Coupling Reactions: Versatility and Practicality
Chen X., Engle K., Wang D., Yu J.
Angewandte Chemie - International Edition , 2009
79.
Recent advances in directed C–H functionalizations using monodentate nitrogen-based directing groups
Zhang M., Zhang Y., Jie X., Zhao H., Li G., Su W.
Organic Chemistry Frontiers , 2014
80.
Direct nucleophilic functionalization of C(sp2)–H-bonds in arenes and hetarenes by electrochemical methods
Shchepochkin A.V., Chupakhin O.N., Charushin V.N., Petrosyan V.A.
Russian Chemical Reviews , 2013
81.
Microwave-assisted palladium-catalyzed C–C coupling versus nucleophilic aromatic substitution of hydrogen (S N H ) in 5-bromopyrimidine by action of bithiophene and its analogues
Verbitskiy E.V., Cheprakova E.M., Zhilina E.F., Kodess M.I., Ezhikova M.A., Pervova M.G., Slepukhin P.A., Subbotina J.O., Schepochkin A.V., Rusinov G.L., Chupakhin O.N., Charushin V.N.
Tetrahedron , 2013
82.
Combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen (SNH) reactions as a versatile route to pyrimidines bearing thiophene fragments
Verbitskiy E.V., Cheprakova E.M., Slepukhin P.A., Kodess M.I., Ezhikova M.A., Pervova M.G., Rusinov G.L., Chupakhin O.N., Charushin V.N.
Tetrahedron , 2012
83.
Synthesis of chiral ferrocenylazines. Negishi cross-coupling or S N H reactions?
Musikhina A.A., Utepova I.A., Serebrennikova P.O., Chupakhin O.N., Charushin V.N.
Russian Journal of Organic Chemistry , 2013
84.
Rupe and Meyer-Schuster rearrangements
Swaminathan S., Narayanan K.V.
Chemical Reviews , 1971
85.
Michaelis-Arbuzov rearrangement
Bhattacharya A.K., Thyagarajan G.
Chemical Reviews , 1981
92.
Free-Radical Phosphonation of Aromatic Compounds
JASON E.F., FIELDS E.K.
Journal of Organic Chemistry , 1962
93.
Oxidative Phosphonylierung von Aromaten mit Cerammoniumnitrat
Kottmann H., Skarzewski J., Effenberger F.
Synthesis , 1987
94.
Oxidative Phosphonylation of Aromatic Compounds
95.
Phosphonation of Arenes with Dialkyl Phosphites Catalyzed by Mn(II)/Co(II)/O2 Redox Couple
Kagayama T., Nakano A., Sakaguchi S., Ishii Y.
Organic Letters , 2006
96.
Silver-Catalyzed Highly Regioselective Phosphonation of Arenes Bearing Electron-Withdrawing Groups
Mao X., Ma X., Zhang S., Hu H., Zhu C., Cheng Y.
European Journal of Organic Chemistry , 2013
98.
Coupling Reactions of Heteroarenes with Phosphites under Silver Catalysis
Xiang C., Bian Y., Mao X., Huang Z.
Journal of Organic Chemistry , 2012
99.
Palladium-catalyzed direct phosphonation of azoles with dialkyl phosphites
Hou C., Ren Y., Lang R., Hu X., Xia C., Li F.
Chemical Communications , 2012
101.
Palladium-Catalyzed Dehydrogenative Cross-Couplings of Benzazoles with Azoles
Han W., Mayer P., Ofial A.R.
Angewandte Chemie - International Edition , 2011
102.
Copper-Mediated Intermolecular Direct Biaryl Coupling
Kitahara M., Umeda N., Hirano K., Satoh T., Miura M.
Journal of the American Chemical Society , 2011
105.
The Nickel/Copper-Catalyzed Direct Alkylation of Heterocyclic CH Bonds
Vechorkin O., Proust V., Hu X.
Angewandte Chemie - International Edition , 2010
107.
Copper-Catalyzed Direct Benzylation or Allylation of 1,3-Azoles with N-Tosylhydrazones
Zhao X., Wu G., Zhang Y., Wang J.
Journal of the American Chemical Society , 2011
108.
Copper-Catalyzed Direct Carboxylation of CH Bonds with Carbon Dioxide
Zhang L., Cheng J., Ohishi T., Hou Z.
Angewandte Chemie - International Edition , 2010
109.
Palladium-Catalyzed Carbonylative CH Activation of Heteroarenes
Wu X., Anbarasan P., Neumann H., Beller M.
Angewandte Chemie - International Edition , 2010
110.
Silver-Mediated Direct Amination of Benzoxazoles: Tuning the Amino Group Source from Formamides to Parent Amines
111.
Direct Amination of Azoles via Catalytic C−H, N−H Coupling
Monguchi D., Fujiwara T., Furukawa H., Mori A.
Organic Letters , 2009
113.
Copper-Catalyzed Direct Sulfoximination of Azoles and Polyfluoroarenes under Ambient Conditions
Miyasaka M., Hirano K., Satoh T., Kowalczyk R., Bolm C., Miura M.
Organic Letters , 2010
114.
Copper-catalyzed addition of H-phosphine oxides to alkynes forming alkenylphosphine oxides
117.
Arylpalladium Phosphonate Complexes as Reactive Intermediates in Phosphorus−Carbon Bond Forming Reactions
Kohler M.C., Grimes T.V., Wang X., Cundari T.R., Stockland R.A.
Organometallics , 2009
118.
Probing the Mechanism of the Heck Reaction with Arene Diazonium Salts by Electrospray Mass and Tandem Mass Spectrometry
Sabino A.A., Machado A.H., Correia C.R., Eberlin M.N.
Angewandte Chemie - International Edition , 2004
119.
Synthesis of Styrenes by Palladium(II)-Catalyzed Vinylation of Arylboronic Acids and Aryltrifluoroborates by Using Vinyl Acetate
Lindh J., Sävmarker J., Nilsson P., Sjöberg P. ., Larhed M.
Chemistry - A European Journal , 2009
120.
Mechanism of Benzoquinone-Promoted Palladium-Catalyzed Oxidative Cross-Coupling Reactions
Hull K.L., Sanford M.S.
Journal of the American Chemical Society , 2009
121.
Benzoquinone-Promoted Reaction of O2with a PdII−Hydride
Decharin N., Stahl S.S.
Journal of the American Chemical Society , 2011
122.
Peroxides as “Switches” of Dialkyl H-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates
Chen X., Li X., Qu L., Tang Y., Mai W., Wei D., Bi W., Duan L., Sun K., Chen J., Ke D., Zhao Y.
Journal of Organic Chemistry , 2014
123.
Antimicrobial properties of some hydroxycoumarins and Fraxinus ornus bark extracts
Kostova I.N., Nikolov N.M., Chipilska L.N.
Journal of Ethnopharmacology , 1993
126.
Inhibition of cell cycle progression in human leukemia HL-60 cells by esculetin
127.
New Caged Coumarin Fluorophores with Extraordinary Uncaging Cross Sections Suitable for Biological Imaging Applications
Zhao Y., Zheng Q., Dakin K., Xu K., Martinez M.L., Li W.
Journal of the American Chemical Society , 2004
128.
Development of an iminocoumarin-based zinc sensor suitable for ratiometric fluorescence imaging of neuronal zinc.
Komatsu K., Urano Y., Kojima H., Nagano T.
Journal of the American Chemical Society , 2007
129.
Polarity-Sensitive Coumarins Tailored to Live Cell Imaging
Signore G., Nifosì R., Albertazzi L., Storti B., Bizzarri R.
Journal of the American Chemical Society , 2010
130.
Design, Synthesis, and Evaluation of Coumarin-Based Molecular Probes for Imaging of Myelination
Wang C., Wu C., Zhu J., Miller R.H., Wang Y.
Journal of Medicinal Chemistry , 2011
131.
Pancreatic anticancer activity of a novel geranylgeranylated coumarin derivative
Devji T., Reddy C., Woo C., Awale S., Kadota S., Carrico-Moniz D.
Bioorganic and Medicinal Chemistry Letters , 2011
132.
Synthesis and Structure-Activity Relationships of Novel Amino/Nitro Substituted 3-Arylcoumarins as Antibacterial Agents
Matos M., Vazquez-Rodriguez S., Santana L., Uriarte E., Fuentes-Edfuf C., Santos Y., Muñoz-Crego A.
Molecules , 2013
134.
10.1002/1521-3773(20011217)40:24<4677::AID-ANIE4677>3.0.CO;2-U
135.
Synthesis and Electrogenerated Chemiluminescence of Donor-Substituted Phenylethynylcoumarins
Elangovan A., Lin J., Yang S., Hsu H., Ho T.
Journal of Organic Chemistry , 2004
137.
Environment-Sensitive Fluorophore Emitting in Protic Environments
Uchiyama S., Takehira K., Yoshihara T., Tobita S., Ohwada T.
Organic Letters , 2006
138.
Development of a Library of 6-Arylcoumarins as Candidate Fluorescent Sensors
Hirano T., Hiromoto K., Kagechika H.
Organic Letters , 2007
140.
Condensation of Triethyl Phosphonoacetate with Aromatic Aldehydes
Robinson C.N., Addison J.F.
Journal of Organic Chemistry , 1966
141.
An efficient synthesis of diethyl coumarin-3-phosphonates
Singh R.K., Rogers M.D.
Journal of Heterocyclic Chemistry , 1985
145.
4-Derivatives Coumarin-3-Phosphonic Acids and Esters
Kostka K., Pastuszko S., Kotyński A., Budzisz E.
Phosphorus, Sulfur and Silicon and the Related Elements , 1998
148.
Manganese(III)-mediated direct phosphonylation of arenes
149.
Manganese(III)-mediated direct phosphonation of arylalkenes and arylalkynes.
Pan X., Zou J., Zhang G., Zhang W.
Chemical Communications , 2010
152.
10.1002/1521-4184(200112)334:12<381::AID-ARDP381>3.0.CO;2-0
153.
A new series of 2-substituted 3-phosphonic derivatives of chromone.
Budzisz E., Graczyk-Wojciechowska J., Zieba R., Nawrot B.
New Journal of Chemistry , 2002
154.
INVESTIGATION IN THE CHROMONE SERIES. PART XX. CHROMONE-3-PHOSPHONIC ACIDS AND ESTERS
Kostka K., Pastuszko S., Porada M.
Phosphorus, Sulfur and Silicon and the Related Elements , 1992
156.
Copper-Catalyzed Aerobic Oxidative Coupling of Terminal Alkynes with H-Phosphonates Leading to Alkynylphosphonates
Gao Y., Wang G., Chen L., Xu P., Zhao Y., Zhou Y., Han L.
Journal of the American Chemical Society , 2009
159.
Alternative synthesis of enantiomeric 1-diphenylphosphino-2-dimethylaminomethylferrocene (Kumada's ligand)
160.
Regioselective palladation of 2-oxazolinyl-[2.2]paracyclophanes.
Bolm C., Wenz K., Raabe G.
Journal of Organometallic Chemistry , 2002
161.
Reactions of Cyclopalladated Complexes with Lithium Diphenylphosphide
Stepanova V.A., Dunina V.V., Smoliakova I.P.
Organometallics , 2009
162.
Design of Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase with Improved Drug Resistance Properties. 1.
Hopkins A.L., Ren J., Milton J., Hazen R.J., Chan J.H., Stuart D.I., Stammers D.K.
Journal of Medicinal Chemistry , 2004
163.
3-Aryl-4-methyl-2-quinolones Targeting MultiresistantStaphylococcus aureusBacteria
Doléans-Jordheim A., Veron J., Fendrich O., Bergeron E., Montagut-Romans A., Wong Y., Furdui B., Freney J., Dumontet C., Boumendjel A.
ChemMedChem , 2013
170.
171
Friedl.
171.
Design and synthesis of phosphole-based π systems for novel organic materials
Matano Y., Imahori H.
Organic and Biomolecular Chemistry , 2009
173.
Modular Synthesis of Benzo[b]phosphole Derivatives via BuLi-Mediated Cyclization of (o-Alkynylphenyl)phosphine
Tsuji H., Sato K., Ilies L., Itoh Y., Sato Y., Nakamura E.
Organic Letters , 2008
176.
Synthesis and Structure-Property Relationships of 2,2′-Bis(benzo[b]phosphole) and 2,2′-Benzo[b]phosphole-Benzo[b]heterole Hybrid π Systems
178.
Direct annulations toward phosphorylated oxindoles: silver-catalyzed carbon-phosphorus functionalization of alkenes.
Li Y., Sun M., Wang H., Tian Q., Yang S.
Angewandte Chemie - International Edition , 2013
179.
Pd(II)-Catalyzed Phosphorylation of Aryl C–H Bonds
Feng C., Ye M., Xiao K., Li S., Yu J.
Journal of the American Chemical Society , 2013
183.
Enantioselective Catalysis with Chiral Phosphine Oxide Preligands
Dubrovina N.V., Börner A.
Angewandte Chemie - International Edition , 2004
185.
Radical aryl migration reactions
Studer A., Bossart M.
Tetrahedron , 2001
186.
Synthesis using aromatic homolytic substitution—recent advances
Bowman W.R., Storey J.M.
Chemical Society Reviews , 2007
188.
Synthesis of Biaryls by Intramolecular Radical Transfer in Phosphinates
Clive D.L., Kang S.
Journal of Organic Chemistry , 2001
192.
Modular synthesis of phenanthridine derivatives by oxidative cyclization of 2-isocyanobiphenyls with organoboron reagents.
195.
196
E. Müller
Z. Elektrochem. , 1910
196.
Hydrophosphorylation of alkenes with dialkyl phosphites catalyzed by Mn(III) under air.
Tayama O., Nakano A., Iwahama T., Sakaguchi S., Ishii Y.
Journal of Organic Chemistry , 2004
198.
New Crinine-Type Alkaloids with Inhibitory Effect on Induction of Inducible Nitric Oxide Synthase from Crinum yemense
Abdel-Halim O.B., Morikawa T., Ando S., Matsuda H., Yoshikawa M.
Journal of Natural Products , 2004
199.
Phenanthridine synthesis via [2+2+2] cyclotrimerization reactions
Sripada L., Teske J.A., Deiters A.
Organic and Biomolecular Chemistry , 2008
200.
New Type of Metalloproteinase Inhibitor:  Design and Synthesis of New Phosphonamide-Based Hydroxamic Acids
Sawa M., Kiyoi T., Kurokawa K., Kumihara H., Yamamoto M., Miyasaka T., Ito Y., Hirayama R., Inoue T., Kirii Y., Nishiwaki E., Ohmoto H., Maeda Y., Ishibushi E., Inoue Y., et. al.
Journal of Medicinal Chemistry , 2002
202.
Palladium-Catalyzed Alkylation of Aryl C−H Bonds with sp3 Organotin Reagents Using Benzoquinone as a Crucial Promoter
Chen X., Li J., Hao X., Goodhue C.E., Yu J.
Journal of the American Chemical Society , 2005
205.
Ligand-Enabled β-C–H Arylation of α-Amino Acids Using a Simple and Practical Auxiliary
Chen G., Shigenari T., Jain P., Zhang Z., Jin Z., He J., Li S., Mapelli C., Miller M.M., Poss M.A., Scola P.M., Yeung K., Yu J.
Journal of the American Chemical Society , 2015
206.
Pyridine-Directed Palladium-Catalyzed Phosphonation of C(sp2)H Bonds
Li C., Yano T., Ishida N., Murakami M.
Angewandte Chemie - International Edition , 2013
209.
Pd-Catalyzed P–C Cross-Coupling Reactions for Versatile Triarylphosphine Synthesis
Hayashi M., Matsuura T., Tanaka I., Ohta H., Watanabe Y.
Organic Letters , 2013
210.
Organophosphorus Chemistry. Addition Reactions of Diethyl Phosphonate and the Oxidation of Triethyl Phosphite1
211.
δ-Bonded 2-Phenylpyridine Palladium Complex
Kasahara A.
Bulletin of the Chemical Society of Japan , 1968
213.
Aromatic substitution of olefin. IV Reaction with palladium metal and silver acetate
Fujiwara Y., Moritani I., Matsuda M., Teranishi S.
Tetrahedron Letters , 1968
214.
Elements of Regiocontrol in Palladium-Catalyzed Oxidative Arene Cross-Coupling
Stuart D.R., Villemure E., Fagnou K.
Journal of the American Chemical Society , 2007
216.
Electrochemical C-H phosphorylation of 2-phenylpyridine in the presence of palladium salts
Dudkina Y.B., Gryaznova T.V., Kataeva O.N., Budnikova Y.H., Sinyashin O.G.
Russian Chemical Bulletin , 2014
217.
Pyridine-directed palladium-catalyzed electrochemical phosphonation of C(sp2)–H bond
Grayaznova T.V., Dudkina Y.B., Islamov D.R., Kataeva O.N., Sinyashin O.G., Vicic D.A., Budnikova Y.Н.
Journal of Organometallic Chemistry , 2015
218.
Electrochemistry of Organophosphorus Compounds
Kargin Y.M., Budnikova Y.G.
Russian Journal of General Chemistry , 2001
219.
221
1960
221.
Electrochemical Synthesis of Nitroaromatic Ketones
Gallardo I., Guirado G., Marquet J.
European Journal of Organic Chemistry , 2002
222.
Electrochemical synthesis of alkyl nitroaromatic compounds.
Gallardo I., Guirado G., Marquet J.
Journal of Organic Chemistry , 2002
223.
Alkylation of nitroaromatics with tetraalkylborate ion via electrochemical oxidation.
Gallardo I., Guirado G., Marquet J.
Journal of Organic Chemistry , 2003
225.
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
226.
Electrochemical Ortho Functionalization of 2-Phenylpyridine with Perfluorocarboxylic Acids Catalyzed by Palladium in Higher Oxidation States
Dudkina Y.B., Mikhaylov D.Y., Gryaznova T.V., Tufatullin A.I., Kataeva O.N., Vicic D.A., Budnikova Y.H.
Organometallics , 2013
228.
Synthesis, Characterization, and Reactivity of a Hexane-Soluble Silver Salt
Stockland R.A., Wilson B.D., Goodman C.C., Giese B.J., Shrimp F.L.
Journal of Chemical Education , 2007
231.
Reductive Elimination from Metal Phosphonate Complexes:  Circumvention of Competing Protonolysis Reactions
Stockland, R.A., Levine A.M., Giovine M.T., Guzei I.A., Cannistra J.C.
Organometallics , 2004
233.
Electronic and Steric Effects on the Reductive Elimination of Diaryl Ethers from Palladium(II)
234.
Direct Observation of C−O Reductive Elimination from Palladium Aryl Alkoxide Complexes To Form Aryl Ethers
Widenhoefer R.A., Zhong H.A., Buchwald S.L.
Journal of the American Chemical Society , 1997
236.
Carbon−Nitrogen-Bond-Forming Reductive Elimination of Arylamines from Palladium(II) Phosphine Complexes
237.
Palladium-Catalyzed Asymmetric Phosphination. Scope, Mechanism, and Origin of Enantioselectivity
Blank N.F., Moncarz J.R., Brunker T.J., Scriban C., Anderson B.J., Amir O., Glueck D.S., Zakharov L.N., Golen J.A., Incarvito C.D., Rheingold A.L.
Journal of the American Chemical Society , 2007
239.
Direct transition metal-catalyzed functionalization of heteroaromatic compounds
240.
C–H functionalization logic in total synthesis
Gutekunst W.R., Baran P.S.
Chemical Society Reviews , 2011
241.
Intermolecular Dehydrogenative Heck Reactions
Le Bras J., Muzart J.
Chemical Reviews , 2011
243.
The Cross-Dehydrogenative Coupling of C sp 3H Bonds: A Versatile Strategy for CC Bond Formations
245.
A Cascade Cross-Coupling Hydrogen Evolution Reaction by Visible Light Catalysis
Meng Q., Zhong J., Liu Q., Gao X., Zhang H., Lei T., Li Z., Feng K., Chen B., Tung C., Wu L.
Journal of the American Chemical Society , 2013
247.
249
A. I. Fedorova
Dokl. Akad. Nauk SSSR , 1961
250.
Nickel-catalyzed C–P cross-coupling of diphenylphosphine oxide with aryl chlorides
Zhang H., Sun M., Ma Y., Tian Q., Yang S.
Organic and Biomolecular Chemistry , 2012
251.
Copper-Catalyzed C-P Coupling through Decarboxylation
Hu J., Zhao N., Yang B., Wang G., Guo L., Liang Y., Yang S.
Chemistry - A European Journal , 2011
252.
Nickel-Catalyzed CP Cross-Coupling by CCN Bond Cleavage
Sun M., Zhang H., Han Q., Yang K., Yang S.
Chemistry - A European Journal , 2011
254.
Synthesis and Biological Evaluation of Aryl-phospho-indole as Novel HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors
Alexandre F., Amador A., Bot S., Caillet C., Convard T., Jakubik J., Musiu C., Poddesu B., Vargiu L., Liuzzi M., Roland A., Seifer M., Standring D., Storer R., Dousson C.B., et. al.
Journal of Medicinal Chemistry , 2010
255.
257
L. Ya. Markovskii
Zh. Neorg. Khim. , 1957
257.
Looking for an Active Conformation of the Future HIV Type-1 Non-Nucleoside Reverse Transcriptase Inhibitors
Regina G.L., Coluccia A., Silvestri R.
Antiviral Chemistry and Chemotherapy , 2010
261.
Copper-catalyzed phosphorylation of sp2C–H bonds
Wang S., Guo R., Wang G., Chen S., Yu X.
Chemical Communications , 2014
262.
Copper-Catalyzed, Directing Group-Assisted Fluorination of Arene and Heteroarene C–H Bonds
Truong T., Klimovica K., Daugulis O.
Journal of the American Chemical Society , 2013
263.
Divergence between Organometallic and Single-Electron-Transfer Mechanisms in Copper(II)-Mediated Aerobic C–H Oxidation
Suess A.M., Ertem M.Z., Cramer C.J., Stahl S.S.
Journal of the American Chemical Society , 2013
264.
Copper‐Catalyzed Intramolecular C(sp3)H and C(sp2)H Amidation by Oxidative Cyclization
Wang Z., Ni J., Kuninobu Y., Kanai M.
Angewandte Chemie - International Edition , 2014