Home / Articles / Methods for selective benzylic C-H oxofunctionalization of organic compounds

Methods for selective benzylic C-H oxofunctionalization of organic compounds

Dmitry Petrovich Lubov 1, 2
Dmitry Petrovich Lubov
, 
Evgenii Pavlovich Talsi 1, 2
Evgenii Pavlovich Talsi
, 
Konstantin Petrovich Bryliakov 1, 2
Konstantin Petrovich Bryliakov
1 Boreskov Institute of Catalysis SB RAS, Novosibirsk
2 Novosibirsk State University
10.1070/RCR4918
Published 30 November 2019
Review , RCR4918, Volume 89, Issue 6, 587-628
36
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Lubov D. P., Talsi E. P., Bryliakov K. P. Methods for selective benzylic C-H oxofunctionalization of organic compounds // Russian Chemical Reviews. 2019. Vol. 89. No. 6. pp. 587-628.
GOST all authors (up to 50)
Copy cite
Lubov D. P., Talsi E. P., Bryliakov K. P. Methods for selective benzylic C-H oxofunctionalization of organic compounds // Russian Chemical Reviews. 2019. Vol. 89. No. 6. pp. 587-628.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RCR4918
UR - https://rcr.colab.ws/publications/10.1070/RCR4918
TI - Methods for selective benzylic C-H oxofunctionalization of organic compounds
T2 - Russian Chemical Reviews
AU - Lubov, Dmitry Petrovich
AU - Talsi, Evgenii Pavlovich
AU - Bryliakov, Konstantin Petrovich
PY - 2019
DA - 2019/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 587-628
IS - 6
VL - 89
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{2019_Lubov,
author = {Dmitry Petrovich Lubov and Evgenii Pavlovich Talsi and Konstantin Petrovich Bryliakov},
title = {Methods for selective benzylic C-H oxofunctionalization of organic compounds},
journal = {Russian Chemical Reviews},
year = {2019},
volume = {89},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4918},
number = {6},
pages = {587--628},
doi = {10.1070/RCR4918}
}
MLA
Cite this
MLA
Copy cite
Lubov, Dmitry Petrovich, et al. “Methods for selective benzylic C-H oxofunctionalization of organic compounds.” Russian Chemical Reviews, vol. 89, no. 6, Nov. 2019, pp. 587-628. https://rcr.colab.ws/publications/10.1070/RCR4918.
Views / Visits / Downloads
33 / 32 / 4

Keywords

Benzylic
C-H activation
homogeneous catalysis
mechanism
selective oxidation

Abstract

The development of methods for the selective oxidation of C-H groups of organic compounds resulting in the formation of C-O bonds is a challenging problem in modern synthetic organic chemistry. Versatile methods for oxofunctionalization of these groups are currently lacking. Approaches for the oxidation of benzylic C-H groups having a relatively weak C-Y bond (the homolytic dissociation energy is ≈80-90 kcal/mol) differ from the methods used for the oxidation of aliphatic and aromatic C-H groups with stronger C-H bonds. The review summarizes homogeneous catalytic and non-catalytic methods for the selective oxofunctionalization of benzylic groups of organic compounds developed in the past 40 years. Reactions involving various oxidizing agents in the presence or in the absence of transition metal compounds are considered. Putative mechanisms of selected transformations are discussed, with a particular focus on selective oxidation of various substrates. The bibliography includes 278 references.

Funders

Ministry of Education and Science of the Russian Federation
АААА-А17-117041710080-4

References

1.
rcr_89_6_587_bib1
2.
rcr_89_6_587_bib2
Serra
2015
3.
Efficient Heterogeneous Oxidation of Alkylarenes with Molecular Oxygen
Kamata K., Kasai J., Yamaguchi K., Mizuno N.
Organic Letters , 2004
5.
Cr-MCM-41-Catalyzed Selective Oxidation of Alkylarenes with TBHP
Das T.K., Chaudhari K., Nandanan E., Chandwadkar A.J., Sudalai A., Ravindranathan T., Sivasanker S.
Tetrahedron Letters , 1997
10.
Synthesis of a reusable polymer anchored cobalt(II) complex for the aerobic oxidation of alkyl aromatics and unsaturated organic compounds
Islam S.M., Ghosh K., Molla R.A., Roy A.S., Salam N., Iqubal M.A.
Journal of Organometallic Chemistry , 2014
15.
Benzocycloarene hydroxylation by P450 biocatalysis
Mayhew M.P., Roitberg A.E., Tewari Y., Holden M.J., Vanderah D.J., Vilker V.L.
New Journal of Chemistry , 2002
16.
Hydrocarbon Hydroxylation by Cytochrome P450 Enzymes
Ortiz de Montellano P.R.
Chemical Reviews , 2009
17.
Chloroperoxidase-catalyzed benzylic hydroxylation.
Miller V.P., Tschirretguth R.A., Demontellano P.R.
Archives of Biochemistry and Biophysics , 1995
18.
Side chain oxidation of aromatic compounds by fungi. 7. A rationale for sulfoxidation, benzylic hydroxylation, and olefin oxidation by Mortierella isabellina
Holland H.L., Allen L.J., Chernishenko M.J., Diez M., Kohl A., Ozog J., Gu J.
Journal of Molecular Catalysis B Enzymatic , 1997
19.
Stereoselective benzylic hydroxylation of 2-substituted indanes using toluene dioxygenase as biocatalyst
Bowers N.I., Boyd D.R., Sharma N.D., Goodrich P.A., Groocock M.R., Blacker A.J., Goode P., Dalton H.
Journal of the Chemical Society Perkin Transactions 1 , 1999
20.
Enantioselective α-Hydroxylation of 2-Arylacetic Acid Derivatives and Buspirone Catalyzed by Engineered Cytochrome P450 BM-3
Landwehr M., Hochrein L., Otey C.R., Kasrayan A., Bäckvall J., Arnold F.H.
Journal of the American Chemical Society , 2006
25.
Manganese terpyridine artificial metalloenzymes for benzylic oxygenation and olefin epoxidation
Zhang C., Srivastava P., Ellis-Guardiola K., Lewis J.C.
Tetrahedron , 2014
26.
Enantioselective Benzylic Hydroxylation Catalysed by P450 Monooxygenases: Characterisation of a P450cam Mutant Library and Molecular Modelling
Eichler A., Gricman Ł., Herter S., Kelly P.P., Turner N.J., Pleiss J., Flitsch S.L.
ChemBioChem , 2016
28.
rcr_89_6_587_bib28
Tan
RSC Adv. , 2017
29.
rcr_89_6_587_bib29
Olofsson
2005
30.
rcr_89_6_587_bib30
Ameta
2014
32.
rcr_89_6_587_bib32
Doherty
2014
33.
rcr_89_6_587_bib33
Chiappe
2008
36.
rcr_89_6_587_bib36
Buckle
2009
39.
Total Syntheses of Ningalins D and G
Kim J., Kim D., Jeon T., Kim W., Cho C.
Organic Letters , 2017
40.
Total Syntheses of Biologically Active Pterocarpan, Isoflavan, and Isoflavanone from Dalbergia oliveri
Singh D.K., Kim J., Sung J., Kim I.
Bulletin of the Korean Chemical Society , 2018
42.
Oxidations by methyl(trifluoromethyl)dioxirane. II: Oxyfunctionalization of saturated hydrocarbons
Mello R., Fiorentino M., Fusco C., Curci R.
Journal of the American Chemical Society , 1989
44.
10.1021/ja012127+
45.
Selective benzylic C–H monooxygenation mediated by iodine oxides
LaMartina K.B., Kuck H.K., Oglesbee L.S., Al-Odaini A., Boaz N.C.
Beilstein Journal of Organic Chemistry , 2019
50.
rcr_89_6_587_bib50
Ojha
2009
55.
Synthesis of structurally diverse diarylketones through the diarylmethyl sp3 CH oxidation
He C., Zhang X., Huang R., Pan J., Li J., Ling X., Xiong Y., Zhu X.
Tetrahedron Letters , 2014
60.
rcr_89_6_587_bib60
Alanthadka
2016
62.
Efficient metal-free aerobic oxidation of aromatic hydrocarbons utilizing aryl-tetrahalogenated N-hydroxyphthalimides and 1,4-diamino-2,3-dichloroanthraquinone
Zhang Q., Chen C., Ma H., Miao H., Zhang W., Sun Z., Xu J.
Journal of Chemical Technology and Biotechnology , 2008
63.
Efficient aerobic oxidation of hydrocarbons with O2catalyzed by DDQ/NHPI
Yang X., Wang Y., Zhou L., Chen C., Zhang W., Xu J.
Journal of Chemical Technology and Biotechnology , 2010
64.
Highly efficient and organic nitrogen-containing cation-promoted aerobic oxidation of alkylaromatics in the presence of N-hydroxyphthalimide
Tong X., Xu J., Miao H., Gao J., Sun Z., Zhang W.
Journal of Chemical Technology and Biotechnology , 2009
65.
Kinetic Studies of Acenaphthene Oxidation Catalyzed by N -Hydroxyphthalimide
Opeida I.O., Litvinov Y.E., Kushch O.V., Kompanets M.O., Shendrik O.M.
International Journal of Chemical Kinetics , 2013
66.
rcr_89_6_587_bib66
Einhorn
1997
67.
Selective catalytic aerobic oxidation of substituted ethylbenzenes under mild conditions
Melone L., Prosperini S., Gambarotti C., Pastori N., Recupero F., Punta C.
Journal of Molecular Catalysis A Chemical , 2012
70.
rcr_89_6_587_bib70
Nakayama
2008
72.
rcr_89_6_587_bib72
Tada
2011
74.
Highly efficient synthesis of 9-fluorenones from 9H-fluorenes by air oxidation
Zhang X., Ji X., Jiang S., Liu L., Weeks B.L., Zhang Z.
Green Chemistry , 2011
75.
t-BuONa-Mediated Transition-Metal-Free Autoxidation of Diarylmethanes to Ketones
Li J., Yang F., Yang Q., Li Z., Chen G., Da Y., Huang P., Chen C., Zhang Y., Huang L.
Synlett , 2017
76.
Transition-Metal-Free C(sp3)–H Oxidation of Diarylmethanes
Yang F., Zhou B., Chen P., Zou D., Luo Q., Ren W., Li L., Fan L., Li J.
Molecules , 2018
78.
Iodosobenzoic Acid (IBA) Catalysed Benzylic and Aromatic C–H Oxidations
Bindu V.H., Parvathaneni S.P., Rao V.J.
Catalysis Letters , 2017
79.
DDQ/tert-Butyl nitrite-catalyzed aerobic oxidation of diarylmethane sp3 C–H bonds
Ma J., Hu Z., Li M., Zhao W., Hu X., Mo W., Hu B., Sun N., Shen Z.
Tetrahedron , 2015
85.
DMSO‐Promoted Metal‐Free Aerobic Oxidation of Heterobenzylic Methylene to Prepare N‐Heterocyclic Ketones
Zhang Y., Yue Y., Wang X., Wang K., Lou Y., Yao M., Zhuo K., Lv Q., Liu J.
Asian Journal of Organic Chemistry , 2018
87.
Direct electrosynthesis of ketones from benzylic methylenes by electrooxidative C-H activation.
Meng L., Su J., Zha Z., Zhang L., Zhang Z., Wang Z.
Chemistry - A European Journal , 2013
88.
Electrochemical benzylic oxidation of C–H bonds
Marko J.A., Durgham A., Bretz S.L., Liu W.
Chemical Communications , 2019
95.
Recent Developments in the ^|^ldquo;Cation Pool^|^rdquo; Method
Yoshida J., Ashikari Y., Matsumoto K., Nokami T.
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry , 2013
96.
Integrated electrochemical-chemical oxidation mediated by alkoxysulfonium ions.
Ashikari Y., Nokami T., Yoshida J.
Journal of the American Chemical Society , 2011
97.
rcr_89_6_587_bib97
Li
1989
98.
Solvent free permanganate oxidations
Shaabani A., Lee D.G.
Tetrahedron Letters , 2001
99.
rcr_89_6_587_bib99
Gannon
1987
100.
2,6-Dicarboxypyridinium Fluorochromate–Promoted Oxidation of Alkyl-Arenes into Carbonyl Compounds Under Nonaqueous and Aprotic Conditions
Sarrafi Y., Tajbakhsh M., Hosseinzadeh R., Sadatshahabi M., Alimohammadi K.
Synthetic Communications , 2011
101.
A Convenient Method of Benzylic Oxidation with Pyridinium Chlorochromate
Rathore R., Saxena N., Chandrasekaran S.
Synthetic Communications , 1986
102.
rcr_89_6_587_bib102
Hosseinzadeh
2005
104.
Enantiocontrolled Total Synthesis of (−)-Mersicarpine
Iwama Y., Okano K., Sugimoto K., Tokuyama H.
Chemistry - A European Journal , 2013
105.
Benzylic oxidation of aromatics with cerium(IV) triflate; synthetic scope and mechanistic insight
Laali K.K., Herbert M., Cushnyr B., Bhatt A., Terrano D.
Journal of the Chemical Society Perkin Transactions 1 , 2001
107.
Benzylic oxidation with palladium(II) acetate
Bryant D.R., McKeon J.E., Ream B.C.
Tetrahedron Letters , 1968
109.
rcr_89_6_587_bib109
Company
2012
110.
Biomimetic nonheme iron catalysts for alkane hydroxylation
Costas M., Chen K., Que L.
Coordination Chemistry Reviews , 2000
112.
Bioinspired oxidations of aliphatic C–H groups with H2O2 in the presence of manganese complexes
Talsi E.P., Ottenbacher R.V., Bryliakov K.P.
Journal of Organometallic Chemistry , 2015
113.
Enantioselective aliphatic C–H bond oxidation catalyzed by bioinspired complexes
Milan M., Bietti M., Costas M.
Chemical Communications , 2018
114.
The Quest for Selectivity in Hydrogen Atom Transfer Based Aliphatic C–H Bond Oxygenation
Milan M., Salamone M., Costas M., Bietti M.
Accounts of Chemical Research , 2018
115.
rcr_89_6_587_bib115
Shilov
2000
116.
Transition metal-catalyzed oxidative transformations of methylarenes
Feng J., Wu X.
Applied Organometallic Chemistry , 2014
117.
rcr_89_6_587_bib117
Mayer
2008
118.
Direct C−H Transformation via Iron Catalysis
Sun C., Li B., Shi Z.
Chemical Reviews , 2010
120.
The selective functionalization of saturated hydrocarbons: Gif chemistry
Barton D.H., Doller D.
Accounts of Chemical Research , 1992
122.
Iron-Catalyzed Benzylic Oxidation with Aqueoustert-Butyl Hydroperoxide
Nakanishi M., Bolm C.
Advanced Synthesis and Catalysis , 2007
123.
Iron-Catalyzed Oxidation of Cycloalkanes and Alkylarenes with Hydrogen Peroxide
Pavan C., Legros J., Bolm C.
Advanced Synthesis and Catalysis , 2005
125.
A Synthetically Useful, Self-Assembling MMO Mimic System for Catalytic Alkene Epoxidation with Aqueous H2O2
White M.C., Doyle A.G., Jacobsen E.N.
Journal of the American Chemical Society , 2001
128.
Non-heme iron catalysts for the benzylic oxidation: a parallel ligand screening approach
Klopstra M., Hage R., Kellogg R.M., Feringa B.L.
Tetrahedron Letters , 2003
132.
C–H benzylic oxidation promoted by dinuclear iron DBDOC iminopyridine complexes
Martínez-Ferraté O., Britovsek G.J., Claver C., van Leeuwen P.W.
Inorganica Chimica Acta , 2015
133.
Fe(TAML)Li/tert-butyl hydroperoxide as a new combination for benzylic C–H oxidation
Napoly F., Kieffer R., Jean-Gérard L., Goux-Henry C., Draye M., Andrioletti B.
Tetrahedron Letters , 2015
135.
Enantioselective Total Synthesis of (−)-Diversonol
Tietze L.F., Jackenkroll S., Raith C., Spiegl D.A., Reiner J.R., Ochoa Campos M.C.
Chemistry - A European Journal , 2013
137.
rcr_89_6_587_bib137
Kamijo
2010
138.
Manganese-Catalyzed Selective Oxidation of Aliphatic CH groups and Secondary Alcohols to Ketones with Hydrogen Peroxide
Dong J.J., Unjaroen D., Mecozzi F., Harvey E.C., Saisaha P., Pijper D., de Boer J.W., Alsters P., Feringa B.L., Browne W.R.
ChemSusChem , 2013
142.
The Isoinversion Principle—a General Model of Chemical Selectivity
Buschmann H., Scharf H., Hoffmann N., Esser P.
Angewandte Chemie - International Edition , 1991
144.
X-Ray Structural Studies of Highly Enantioselective Mn(salen) Epoxidation Catalysts
Pospisil P.J., Carsten D.H., Jacobsen E.N.
Chemistry - A European Journal , 1996
145.
1H NMR and EPR spectroscopic monitoring of the reactive intermediates of (Salen)MnIII catalyzed olefin epoxidation
Bryliakov K.P., Babushkin D.E., Talsi E.P.
Journal of Molecular Catalysis A Chemical , 2000
146.
rcr_89_6_587_bib146
Blay
2001
148.
rcr_89_6_587_bib148
Sherman
J. Biol. Chem. , 2006
149.
Analysis of Transient and Catalytic Desosamine-binding Pockets in Cytochrome P-450 PikC from Streptomyces venezuelae
Li S., Ouellet H., Sherman D.H., Podust L.M.
Journal of Biological Chemistry , 2009
150.
Predictable Stereoselective and Chemoselective Hydroxylations and Epoxidations with P450 3A4
Larsen A.T., May E.M., Auclair K.
Journal of the American Chemical Society , 2011
153.
A moderate and efficient method for oxidation of ethylbenzene with hydrogen peroxide catalyzed by 8-quinolinolato manganese(III) complexes
Lu C., Fu Z., Liu Y., Liu F., Wu Y., Qin J., He X., Yin D.
Journal of Molecular Catalysis A Chemical , 2010
154.
Electron deficient manganese(III) corrole catalyzed oxidation of alkanes and alkylbenzenes at room temperature
Bose S., Pariyar A., Biswas A.N., Das P., Bandyopadhyay P.
Catalysis Communications , 2011
155.
Selective Catalytic Oxidation of Alcohols, Aldehydes, Alkanes and Alkenes Employing Manganese Catalysts and Hydrogen Peroxide
Saisaha P., Buettner L., van der Meer M., Hage R., Feringa B.L., Browne W.R., de Boer J.W.
Advanced Synthesis and Catalysis , 2013
163.
rcr_89_6_587_bib163
Jin
2011
165.
rcr_89_6_587_bib165
Nawratil
2014
169.
Ruthenium-catalyzed cytochrome P-450 type oxidation of alkanes with alkyl hydroperoxides
Murahashi S., Oda Y., Naota T., Kuwabara T.
Tetrahedron Letters , 1993
170.
Ruthenium-Catalyzed Oxidation of Alkanes with tert-Butyl Hydroperoxide and Peracetic Acid
Murahashi S., Komiya N., Oda Y., Kuwabara T., Naota T.
Journal of Organic Chemistry , 2000
176.
Speciation and decomposition pathways of ruthenium catalysts used for selective C–H hydroxylation
Flender C., Adams A.M., Roizen J.L., McNeill E., Du Bois J., Zare R.N.
Chemical Science , 2014
177.
Supramolecular catalysis. Part 2: artificial enzyme mimics.
Raynal M., Ballester P., Vidal-Ferran A., van Leeuwen P.W.
Chemical Society Reviews , 2014
178.
Supramolecular catalysis. Part 1: non-covalent interactions as a tool for building and modifying homogeneous catalysts
Raynal M., Ballester P., Vidal-Ferran A., van Leeuwen P.W.
Chemical Society Reviews , 2014
179.
Enantiotopos-selective C-H oxygenation catalyzed by a supramolecular ruthenium complex.
Frost J.R., Huber S.M., Breitenlechner S., Bannwarth C., Bach T.
Angewandte Chemie - International Edition , 2014
180.
Benzylic Oxidation Catalyzed by Dirhodium(II,III) Caprolactamate
Catino A.J., Nichols J.M., Choi H., Gottipamula S., Doyle M.P.
Organic Letters , 2005
181.
rcr_89_6_587_bib181
Wusiman
2012
182.
Rh2(esp)2-catalyzed allylic and benzylic oxidations
Wang Y., Kuang Y., Wang Y.
Chemical Communications , 2015
183.
rcr_89_6_587_bib183
Coelho
2013
185.
Chromium-catalyzed oxidation of benzylcyclopropane with tert-butyl hydroperoxide
Ajjou A.N., Riahi A., Chatterjee D., Muzart J.
Catalysis Communications , 2006
190.
rcr_89_6_587_bib190
Muzart
Tetrahedron Lett. , 1995
193.
Nickel-Catalyzed Benzylic Oxidation with NaOCl
Yamazaki S.
Synthetic Communications , 1999
194.
Bismuth-Catalyzed Benzylic Oxidations with tert-Butyl Hydroperoxide
Bonvin Y., Callens E., Larrosa I., Henderson D.A., Oldham J., Burton A.J., Barrett A.G.
Organic Letters , 2005
196.
Oxidation and Amination of Benzylic sp3 C–H Bond Catalyzed by Rhenium(V) Complexes
Peng H., Lin A., Zhang Y., Jiang H., Zhou J., Cheng Y., Zhu C., Hu H.
ACS Catalysis , 2011
198.
rcr_89_6_587_bib198
Zhou
J. Am. Chem. Soc. , 2010
199.
Cp* Iridium Precatalysts for Selective C–H Oxidation with Sodium Periodate As the Terminal Oxidant
Zhou M., Hintermair U., Hashiguchi B.G., Parent A.R., Hashmi S.M., Elimelech M., Periana R.A., Brudvig G.W., Crabtree R.H.
Organometallics , 2013
200.
Stoichiometric and Catalytic Oxygen Activation by Trimesityliridium(III)
Jacobi B.G., Laitar D.S., Pu L., Wargocki M.F., DiPasquale A.G., Fortner K.C., Schuck S.M., Brown S.N.
Inorganic Chemistry , 2002
201.
Aerobic oxidation with N-hydroxyphthalimide catalysts in ionic liquid
Wang J., Liu L., Wang Y., Zhang Y., Deng W., Guo Q.
Tetrahedron Letters , 2005
205.
rcr_89_6_587_bib205
Nechab
2004
206.
rcr_89_6_587_bib206
Orlińska
Cent. Eur. J. Chem. , 2011
207.
NHPI and ferric nitrate: a mild and selective system for aerobic oxidation of benzylic methylenes
Miao C., Zhao H., Zhao Q., Xia C., Sun W.
Catalysis Science and Technology , 2016
209.
A promotion effect of alkaline-earth chloride on N-hydroxyphthalimide-catalyzed aerobic oxidation of hydrocarbons
Yang X., Zhou L., Chen Y., Chen C., Su Y., Miao H., Xu J.
Catalysis Communications , 2009
210.
Recent Advances in Homogeneous Metal-Catalyzed Aerobic C–H Oxidation of Benzylic Compounds
Urgoitia G., SanMartin R., Herrero M., Domínguez E.
Catalysts , 2018
211.
Catalytic Aerobic Oxidation of C(sp 3 )−H Bonds
Sterckx H., Morel B., Maes B.U.
Angewandte Chemie - International Edition , 2019
213.
Copper-Catalyzed Aerobic Oxygenation of BenzylpyridineN-Oxides and Subsequent Post-Functionalization
Sterckx H., Sambiagio C., Médran-Navarrete V., Maes B.U.
Advanced Synthesis and Catalysis , 2017
214.
Triprolidine Radioimmunoassay: Disposition in Animals and Humans
Findlayx J.W., Butz R.F., Coker G.G., Deangelis R.L., Welch R.M.
Journal of Pharmaceutical Sciences , 1984
215.
rcr_89_6_587_bib215
216.
Synthesis of Aryl(di)azinyl Ketones through Copper- and Iron-catalyzed Oxidation of the Methylene Group of Aryl(di)azinylmethanes
De Houwer J., Abbaspour Tehrani K., Maes B.U.
Angewandte Chemie - International Edition , 2012
217.
Mechanism of the CuII-catalyzed benzylic oxygenation of (aryl)(heteroaryl)methanes with oxygen
Sterckx H., De Houwer J., Mensch C., Caretti I., Tehrani K.A., Herrebout W.A., Van Doorslaer S., Maes B.U.
Chemical Science , 2016
218.
Chloroacetate-Promoted Selective Oxidation of Heterobenzylic Methylenes under Copper Catalysis
Liu J., Zhang X., Yi H., Liu C., Liu R., Zhang H., Zhuo K., Lei A.
Angewandte Chemie - International Edition , 2014
221.
Aerobic oxidation of alkanes and alkenes in the presence of aldehydes catalyzed by copper salts and copper-crown ether
Komiya N., Naota T., Oda Y., Murahashi S.
Journal of Molecular Catalysis A Chemical , 1997
223.
Dehydrogenative α-Oxygenation of Ethers with an Iron Catalyst
Gonzalez-de-Castro A., Robertson C.M., Xiao J.
Journal of the American Chemical Society , 2014
224.
Aerobic oxidation at benzylic positions catalyzed by a simple Pd(OAc)2/bis-triazole system
Urgoitia G., Maiztegi A., SanMartin R., Herrero M.T., Domínguez E.
RSC Advances , 2015
225.
An outstanding catalyst for the oxygen-mediated oxidation of arylcarbinols, arylmethylene and arylacetylene compounds
Urgoitia G., SanMartin R., Herrero M.T., Domínguez E.
Chemical Communications , 2015
228.
Organic Photoredox Catalysis
Romero N.A., Nicewicz D.A.
Chemical Reviews , 2016
229.
Photocatalytic Oxidation of Hydrocarbons by a Bis-iron(III)-μ-oxo Pacman Porphyrin Using O2 and Visible Light
Rosenthal J., Luckett T.D., Hodgkiss J.M., Nocera D.G.
Journal of the American Chemical Society , 2006
230.
Direct Benzylic CH Activation for CO Bond Formation by Photoredox Catalysis
Pandey G., Pal S., Laha R.
Angewandte Chemie - International Edition , 2013
232.
rcr_89_6_587_bib232
Yi
Chem. Commun. , 2015
233.
Light-Driven, Proton-Controlled, Catalytic Aerobic C–H Oxidation Mediated by a Mn(III) Porphyrinoid Complex
Neu H.M., Jung J., Baglia R.A., Siegler M.A., Ohkubo K., Fukuzumi S., Goldberg D.P.
Journal of the American Chemical Society , 2015
243.
Direct Oxidation of Csp3 -H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow.
Lesieur M., Battilocchio C., Labes R., Jacq J., Genicot C., Ley S.V., Pasau P.
Chemistry - A European Journal , 2018
244.
rcr_89_6_587_bib244
Irie
2012
247.
Hydroxylation of alkanes catalysed by a chiral μ-oxo diferric complex: a metal-based mechanism
Mekmouche Y., Duboc-Toia C., Ménage S., Lambeaux C., Fontecave M.
Journal of Molecular Catalysis A Chemical , 2000
251.
rcr_89_6_587_bib251
Gosiewska
2007
252.
Water as an Oxygen Source in the Generation of Mononuclear Nonheme Iron(IV) Oxo Complexes
Lee Y., Dhuri S., Sawant S., Cho J., Kubo M., Ogura T., Fukuzumi S., Nam W.
Angewandte Chemie - International Edition , 2009
253.
rcr_89_6_587_bib253
Zhang
Inorg. Chem. , 2013
256.
rcr_89_6_587_bib256
Halterman
Tetrahedron , 1997
259.
Site- and Enantioselective C−H Oxygenation Catalyzed by a Chiral Manganese Porphyrin Complex with a Remote Binding Site
Burg F., Gicquel M., Breitenlechner S., Pöthig A., Bach T.
Angewandte Chemie - International Edition , 2018
260.
Kinetic Resolution of 1,2-Dihydronaphthalene Oxide and Related Epoxides via Asymmetric C-H Hydroxylation
Larrow J.F., Jacobsen E.N.
Journal of the American Chemical Society , 1994
261.
Asymmetric benzylic oxidation using a Mn-salen complex as catalyst
Hamachi K., Irie R., Katsuki T.
Tetrahedron Letters , 1996
269.
Diphenylmethane Oxidation Catalyzed by Mononuclear Mn(III) Complexes
Golchoubian H., Ghasemi N.
Journal of the Chinese Chemical Society , 2011
270.
Mechanism of Selective C–H Hydroxylation Mediated by Manganese Aminopyridine Enzyme Models
Ottenbacher R.V., Talsi E.P., Bryliakov K.P.
ACS Catalysis , 2014
272.
Chemoselective Aliphatic C–H Bond Oxidation Enabled by Polarity Reversal
Dantignana V., Milan M., Cussó O., Company A., Bietti M., Costas M.
ACS Central Science , 2017
274.
rcr_89_6_587_bib274
Zhang
1999
276.
Ruthenium(II) complexes of hybrid 8-hydroxyquinoline-thiosemicarbazone ligands: synthesis, characterization and catalytic applications
Nirmala M., Manikandan R., Prakash G., Viswanathamurthi P.
Applied Organometallic Chemistry , 2013
277.
Catalytic asymmetric oxidations using molecular oxygen
Ottenbacher R.V., Talsi E.P., Bryliakov K.P.
Russian Chemical Reviews , 2018
278.
Recent advances in catalytic asymmetric dihydroxylation of olefins
Ottenbacher R.V., Talsi E.P., Bryliakov K.P.
Russian Chemical Reviews , 2019