- Ferric ion concentration-controlled aerobic photo-oxidation of benzylic C–H bond with high selectivity and conversion
-
A Fe(III)-promoted highly selective photo-oxidation of benzylic C–H bond delivering relative carbonyl products is reported. By altering the concentration of ferric salt, methylarenes can be selectively oxidized under UV irradiation to furnish aromatic aldehydes or acids, respectively. By this protocol, the oxidation of ethylarenes provides the corresponding acetophenones. The reaction is inferred to involve divergent pathways in different concentrations of catalyst for the alternative selectivity between aldehydes and aicds. The reusable catalyst, high conversion and selectivity make this oxidation a green and economic protocol for the synthesis of aromatic carbonyl compounds.
- Bu, Hongzhong,Gu, Jiefan,Li, Yufeng,Ma, Hongfei,Wan, Yuting,Wu, Zheng-Guang,Zhang, Weijian,Zhou, Ying'ao,Zhu, Hongjun
-
-
- Visible-Spectrum Solar-Light-Mediated Benzylic C-H Oxygenation Using 9,10-Dibromoanthracene As an Initiator
-
We report a visible-light-mediated benzylic C-H oxygenation reaction. The reaction is initiated by solar light or the blue LED activation of 9,10-dibromoanthracene in a reaction with oxygen and takes place at ambient temperature and air pressure. Secondary benzylic positions are oxygenated to ketones, while tertiary benzylic carbons are oxygenated to give hydroperoxides. Notably, cumene hydroperoxide is produced in a higher yield and at milder conditions than the currently employed industrial conditions.
- Santra, Sourav K.,Szpilman, Alex M.
-
p. 1164 - 1171
(2020/12/23)
-
- Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis
-
A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.
- García Manche?o, Olga,Kuhlmann, Jan H.,Pérez-Aguilar, María Carmen,Piekarski, Dariusz G.,Uygur, Mustafa
-
supporting information
p. 3392 - 3399
(2021/05/21)
-
- An expeditious and efficient method for the oxidation of benzyl alcohols by homogeneous electrolysis
-
A greener and inexpensive electrochemical method has been developed for the oxidation of benzyl alcohols by homogeneous electrolysis. The electrochemical reaction was carried out in an undivided cell equipped with carbon and stainless steel electrodes at room temperature. The homogeneous solution made up of acetonitrile/water containing substrate and ammonium bromide with a catalytic amount of H2SO4 as supporting electrolyte. The reaction condition was optimized with various electrochemical experimental parameters and evaluated with various substituted benzyl alcohols to result in excellent yield of aldehydes (>83%).
- Jagatheesan, Rathinavel,Shanmugavelan, Poovan,Sambathkumar, Subramaniyan,Ramesh, Pugalenthi
-
supporting information
p. 3013 - 3022
(2021/08/12)
-
- LIGHT INDUCED CATALYTIC C-H OXYGENATION OF ALKANES
-
A method of oxygenating a benzylic C-H bond is provided. The method comprises light induced activation of an initiator and subsequent reaction with oxygen, resulting in the formation of free radicals. Subsequently, free radicals catalyze the reaction of the benzylic C-H bond with oxygen, thereby forming an oxygenated compound.
- -
-
Paragraph 00219
(2021/04/02)
-
- Reaction method for selectively synthesizing aromatic aldehyde or aromatic carboxylic acid
-
The invention provides a reaction method for selectively synthesizing aromatic aldehyde or aromatic carboxylic acid. Toluene aromatic hydrocarbon without substituent or with substituent on a benzene ring is used as a raw material, an inorganic salt of ferric iron is used as a catalyst, air or oxygen is used as an oxidizing agent, a mixed solution of acetonitrile and water is used as a solvent, theraw material is oxidized by adjusting the dosage of the catalyst to obtain aromatic aldehyde or aromatic carboxylic acid, and the aromatic aldehyde or aromatic carboxylic acid is irradiated by ultraviolet light for 10-16 hours. Aromatic carboxylic acid obtained under the condition that the dosage of the catalyst is 5-50% mol of aromatic hydrocarbon is used as a main product, wherein the use amount of the catalyst is 70-200% mol of aromatic hydrocarbon. The reaction method provided by the invention has the characteristics of atom economy and high selectivity, uses the metal iron salt with richearth content for catalysis, and has the advantages of mild conditions, recyclable catalyst and solvent and the like.
- -
-
Paragraph 0033-0034
(2020/12/05)
-
- Clean Ar-Me conversion to Ar-aldehyde with the aid of carefully designed metallocorrole photocatalysts
-
Toluene, p-xylene and mesitylene were cleanly converted to their corresponding monoaldehydes via mild photooxygenation utilizing transition metal and main group β-CF3-substituted corroles. Aldehyde yield increased as more electron-donating CH3 groups are present on the substrate. 4-P was most efficient (TON ~ 1072, mesitylene) via the singlet oxygen vis the superoxide mechanism.
- Chen, Qiu-Cheng,Churchill, David G.,Fite, Shachar,Gross, Zeev,Kolanu, Sudhakar,Lee, Woohyun,Zhan, Xuan
-
p. 996 - 1000
(2020/08/28)
-
- Method for reducing carboxylic acid into aldehyde compounds
-
The invention discloses a method for reducing carboxylic acid into aldehyde compounds, and belongs to the field of organic chemical synthesis. Specifically, in an argon atmosphere, a carboxylic acid compound, a transition metal nickel compound, an anhydride compound, a ligand and a reducing agent are dissolved in an organic solvent, the mixture is heated and subjected to stirring reaction, after the reaction is finished, the pressure is reduced to remove the organic solvent, column chromatography separation is performed, and various aldehyde compounds are obtained. The method has the advantages of simple synthesis steps, mild reaction conditions, simplicity and easiness in operation, realization of successful reduction of the carboxylic acid compound into the aldehyde organic compounds, small use amount of the reaction catalyst, high product yield, and provision of a new approach for reduction of the carboxylic acid compound into the aldehyde compounds. Compared with a conventional method, the method has the advantages that raw materials are cheap, easy to obtain and environmentally friendly, substrate universality and functional group compatibility are improved, and the method hascertain innovativeness and unique research significance in organic synthesis methodology.
- -
-
Paragraph 0047-0050
(2020/02/27)
-
- Development of a polymer embedded reusable heterogeneous oxovanadium(IV)catalyst for selective oxidation of aromatic alkanes and alkenes using green oxidant
-
A new heterogeneous polymer supported solid phase oxovanadium(IV)catalyst was synthesized successfully. The designed catalyst furnished excellent results in the oxidation reactions of various aromatic alkanes, e.g. toluene, para-xylene, mesitylene. The polymer supported vanadium complex was proved also an efficient catalyst for the oxidation of aromatic alkenes, like substituted styrenes, trans-stilbene, etc. under mild reaction conditions. The supported catalyst was nicely elucidated by SEM-EDAX, TGA, FT-IR and UV–Vis spectral analysis. The catalytic activity was tested in the presence of an environment-friendly oxidant, 30% aqueous H2O2 during the oxidation of broad range of substrates. Another important fact is that the designed oxovanadium(IV)catalyst is heterogeneous in nature. Moreover, the newly synthesized oxovanadium(IV)complex exhibited a notable recoverability and it could be recycled up to six runs devoid of any prominent reduction in catalytic behavior.
- Paul, Priyanka,Ghosh, Aniruddha,Chatterjee, Sauvik,Bera, Apurba,Alam, Seikh Mafiz,Islam, Sk. Manirul
-
p. 198 - 212
(2019/05/01)
-
- Method for preparing 3,5-dimethyl benzaldehyde by efficiently catalyzing sym-trimethylbenzene
-
The invention belongs to the technical field of polyoxometallate catalysts, and relates to a method for preparing 3,5-dimethyl benzaldehyde by catalytically oxidizing sym-trimethylbenzene with a polyoxometallate (Keggin type, Dawson type, Silverton type, Waugh type, Lindquist type, Anderson type and the like) catalyst. The polyoxometallate is adopted as the catalyst and placed in a reactor, then an organic solvent and the sym-trimethylbenzene are added in sequence, finally an oxidizing agent is added, stirring and reacting are carried out for 12-48 hours at the temperature of 50 DEG C to 80 DEG C, separation is carried out, and the 3,5-dimethyl benzaldehyde is obtained. Compared with the prior art, the method is easy to operate and mild in condition, the method for preparing the 3,5-dimethyl benzaldehyde has atom economy and environmental friendliness, the conversion rate of the sym-trimethylbenzene and the selectivity of the 3,5-dimethyl benzaldehyde are high, the catalyst has the advantages of being green, efficient, easy to recycle and the like, and application and popularization value is achieved.
- -
-
Paragraph 0023-0056
(2019/08/20)
-
- Efficient catalytic oxidation of methyl aromatic hydrocarbon with: N -alkyl pyridinium salts
-
A series of N-alkyl pyridinium salts were synthesized and employed as metal-free catalyst for the selective oxidation of methyl aromatic hydrocarbon with molecular oxygen. The electronic effect of the substitutes was found to be an important factor for the catalytic performance. With the introduction of electron-donating substitute -N(CH3)2, the conversion of p-xylene and selectivity of p-toluic acid could be simultaneously increased. 1-Benzyl-4-N,N-dimethylaminopyridinium salt showed the highest catalytic activity, and 95% conversion with 84% of selectivity to p-toluic acid could be obtained for the selective oxidation of p-xylene. Several methyl aromatic hydrocarbons could all be efficiently oxidized with the reported catalyst at the absence of any metal species.
- Zhang, Qiaohong,He, Honghao,Wang, Huibin,Zhang, Zhan,Chen, Chen
-
p. 38891 - 38896
(2019/12/11)
-
- Photocatalytic Oxygenation Reactions with a Cobalt Porphyrin Complex Using Water as an Oxygen Source and Dioxygen as an Oxidant
-
Photocatalytic oxygenation of hexamethylbenzene occurs under visible-light irradiation of an O2-saturated acetonitrile solution containing a cobalt porphyrin complex CoII(TPP) (TPP2- = tetraphenylporphyrin dianion), water, and triflic acid (HOTf) via a one-photon-two-electron process, affording pentamethylbenzyl alcohol and hydrogen peroxide as products with a turnover number of >6000; in this reaction, H2O and O2 were used as an oxygen source and a two-electron oxidant, respectively. The photocatalytic mechanism was clarified by means of electron paramagnetic resonance, time-resolved fluorescence, and transient absorption measurements as well as 18O-labeling experiments with H218O and 18O2. To the best of our knowledge, we report the first example of efficient photocatalytic oxygenation of an organic substrate by a metal complex using H2O as an oxygen source and O2 as a two-electron oxidant.
- Hong, Young Hyun,Han, Ji Won,Jung, Jieun,Nakagawa, Tatsuo,Lee, Yong-Min,Nam, Wonwoo,Fukuzumi, Shunichi
-
supporting information
p. 9155 - 9159
(2019/06/21)
-
- Aliphatic amines modified CoO nanoparticles for catalytic oxidation of aromatic hydrocarbon with molecular oxygen
-
The surface modification of metal oxides using organic modifiers is a potential strategy for enhancing their catalytic performances. In this study, a hydrophobic surface amine-modified CoO catalyst with a water contact angle of 143° was fabricated. The catalyst was characterized by XRD, TGA, FT-IR, HR-TEM, and XPS. The results showed that the fabricated catalyst performed better than the hydrophilic commercial CoO nanoparticle in the process of aromatic hydrocarbon oxidation. After the amines modification, commercial CoO also became hydrophobic and improved conversion of ethylbenzene was achieved. The surface modification of CoO with amines induced the hydrophobicity property, which could serve as a reference for the design of other hydrophobic catalysts.
- Liu, Meng,Shi, Song,Zhao, Li,Chen, Chen,Gao, Jin,Xu, Jie
-
p. 1488 - 1493
(2019/09/09)
-
- Polymer-incarcerated palladium-catalyzed facile: In situ carbonylation for the synthesis of aryl aldehydes and diaryl ketones using CO surrogates under ambient conditions
-
In this existing work, an efficient polymer-supported palladium catalyst, a furfurylamine-functionalized Merrifield complex of palladium [Pd@(Merf-FA)], was synthesized and characterized, showing excellent catalytic activity towards in situ carbonylation reactions using carbon monoxide surrogates like formic acid and chloroform. Herein, we examined the catalytic activity of the Pd@(Merf-FA) catalyst for the formylation of aryl iodides and carbonylative Suzuki-Miyaura coupling reactions. The Pd@(Merf-FA) catalyst was systematically characterized by several techniques like HRTEM, elemental mapping, PXRD, TGA-DTA, FESEM, UV-vis, EDAX, CHN and AAS analysis. The catalyst is highly recyclable, able to be recycled up to six times without showing any significant decrease in catalytic activity. The [Pd@(Merf-FA)] catalyst proved to be more efficient compared to the corresponding homogeneous palladium catalyst. In addition, the leaching experiment of the synthesized catalyst was studied, which showed that negligible leaching of metal occurred from the polymeric support.
- Dey, Tusar Kanto,Basu, Priyanka,Riyajuddin, Sk,Ghosh, Aniruddha,Ghosh, Kaushik,Manirul Islam, Sk
-
p. 9802 - 9814
(2019/07/04)
-
- Benzylation of Arenes with Benzyl Halides under Promoter-Free and Additive-Free Conditions
-
It was found that benzyl chlorides and bromides could directly react with electron-rich arenes, which provided an example of promoter-free and additive-free benzylation of arenes. A variety of benzyl chlorides and bromides were treated with benzene rings to give the targeted products in low to high yields. The present conditions tolerated the vinyl group of the substrates. Preliminary mechanistic investigation suggests that the present reactions possibly proceed via an autocatalytic mechanism pathway.
- Cheng, Xinqiang,Shan, Jiankai,Tian, Xinshe,Ren, Yun-Lai,Zhu, Yanyan
-
p. 4404 - 4410
(2019/07/03)
-
- Assessing the effectiveness of oxidative approaches for the synthesis of aldehydes and ketones from oxidation of iodomethyl group
-
Owing to excellent selectivity, high yield and stability towards over-reduction and over-oxidation, one of the impressive approaches to synthesize aldehydes and ketones is the oxidation of halomethyl groups. Numerous halomethyl oxidation-based methodologies to afford aldehydes and ketones are disclosed in the literature. Mostly, chloromethyl or bromomethyl group containing substrates have been used in the literature for performing oxidation. There are negligible data available in the literature that addresses the use of iodomethyl group containing substrates for transformation to aldehydes and ketones. In this research work, 110 reactions have been carried out to construct aldehydes and ketones from oxidation of iodomethyl group in benzylic iodides and allylic iodides using numerous well-known approaches reported in the literature. The classical approaches under observation include Sommelet oxidation, Kr?hnke oxidation, sodium periodate-mediated oxidative protocol, manganese dioxide-based oxidative approach, Kornblum oxidation and Hass–Bender oxidation. The eco-friendly approaches under observation include periodic acid-based IL protocol, periodic acid in vanadium pentoxide-mediated IL method, hydrogen peroxide in vanadium pentoxide-based approach and bismuth nitrate-promoted IL technique. In this investigation, yield, recyclability, cost-effectiveness, eco-friendliness and over-oxidation are the main parameters which are under observation. Among all these investigated techniques, periodic acid-based IL protocol, periodic acid in vanadium pentoxide-mediated IL method and hydrogen peroxide in vanadium pentoxide-based approach (aka. Chunbao oxidation protocol) were found to be highly efficient due to the following reasons: these approaches (1) provide excellent yields, (2) do not lead towards over-oxidation, (3) show good recyclability, (4) demonstrate high thermal stability and negligible flammability, and (5) require no special handling.
- Faisal, Muhammad,Hussain, Sarwat,Haider, Azeem,Saeed, Aamer,Larik, Fayaz Ali
-
p. 1053 - 1067
(2019/04/25)
-
- Efficient acceptorless photo-dehydrogenation of alcohols and: N -heterocycles with binuclear platinum(ii) diphosphite complexes
-
Although photoredox catalysis employing Ru(ii) and Ir(iii) complexes as photocatalysts has emerged as a versatile tool for oxidative C-H functionalization under mild conditions, the need for additional reagents acting as electron donor/scavenger for completing the catalytic cycle undermines the practicability of this approach. Herein we demonstrate that photo-induced oxidative C-H functionalization can be catalysed with high product yields under oxygen-free and acceptorless conditions via inner-sphere atom abstraction by binuclear platinum(ii) diphosphite complexes. Both alcohols (51 examples), particularly the aliphatic ones, and saturated N-heterocycles (24 examples) can be efficiently dehydrogenated under light irradiation at room temperature. Regeneration of the photocatalyst by means of reductive elimination of dihydrogen from the in situ formed platinum(iii)-hydride species represents an alternative paradigm to the current approach in photoredox catalysis.
- Zhong, Jian-Ji,To, Wai-Pong,Liu, Yungen,Lu, Wei,Che, Chi-Ming
-
p. 4883 - 4889
(2019/05/16)
-
- Palladium-Catalyzed Reductive Conversion of Acyl Fluorides via Ligand-Controlled Decarbonylation
-
Ligand-controlled non-decarbonylative and decarbonylative conversions of acyl fluorides were developed using a Pd(OAc)2/Et3SiH combination. When tricyclohexylphosphine (PCy3) was used as the ligand, aldehydes were obtained as simple reductive conversion products. The use of 1,2-bis(dicyclohexylphosphino)ethane (Cy2P(CH2)2PCy2, DCPE) as the ligand, however, favored the formation of hydrocarbons, which are decarbonylative reduction products.
- Ogiwara, Yohei,Sakurai, Yuka,Hattori, Hiroyuki,Sakai, Norio
-
supporting information
p. 4204 - 4208
(2018/07/29)
-
- Method for preparing aromatic aldehydes by using graphene oxide-titanium sulfate nano composite
-
The invention discloses a method for preparing aromatic aldehydes by using a graphene oxide-titanium sulfate nano composite (GO-Ti), and belongs to the technical field of fine chemical product preparation. According to the method, aromatic benzyl alcohols with different structures are taken as reaction substrates, tetrahydrofuran and the like are used as solvents, a hydrogen peroxide solution is used as an oxidizing agent, an oxidation reaction is carried out under the action of a GO-Ti nano composite catalyst, and the aromatic aldehydes are obtained by column chromatography or reduced pressure distillation after the reaction is finished, wherein the reaction temperature is 50-70 DEG C and the reaction time is 3-12 hours. The synthesis method provided by the invention is simple, the used solvents all can be recycled, the oxidation also can be carried out without solvents, the operation is convenient, the reaction conditions are mild, the economic benefit is high, and the environment isfree from pollution. The catalyst still has high conversion rate and selectivity after being recycled and used for 10 times.
- -
-
Paragraph 0043-0045
(2018/09/08)
-
- Pseudohalide assisted aerobic oxidation of alcohols in the presence of visible-light
-
Pseudohalides are well known to do similar chemistry like halides. Thiocyanate, a pseudohalide acts like halides in many ways. Thiocyanate radicals ([rad]SCN) are generated from readily available thiocyanate salts using Rose Bengal through single electron transfer (SET) in the presence of visible light. Thiocyanate radicals abstract hydrogen like other halide radicals, so this aspect of chemistry was used for the oxidation of alcohols to their corresponding aldehydes using oxygen as the terminal oxidant. This method shows a broad scope and well tolerance towards various functional groups.
- Sheriff Shah, Sk,Pradeep Singh
-
supporting information
p. 247 - 251
(2018/01/03)
-
- Highly efficient and green oxidation of alkanes and alkylaromatics with hydrogen peroxide catalysed by silver and vanadyl on mesoporous silica-coated magnetite
-
A heterogeneous catalyst (FeSi/Ag/VO) based on silver and vanadyl as active sites and mesoporous silica-coated nanospheres of magnetite (Fe3O4@m-SiO2) as support was successfully prepared by deposition of Ag nanoparticles and the covalent grafting of vanadyl(IV) acetylacetonate on Fe3O4@m-SiO2. The catalyst exhibited excellent activity for the oxidation of alkanes, benzene and alkylaromatics using green oxidant H2O2 and oxalic acid in acetonitrile at 60?°C.
- Nouri, Seyed Hadi,Hosseini-Monfared, Hassan
-
-
- Selective Aerobic Oxidation of Methylarenes to Benzaldehydes Catalyzed by N-Hydroxyphthalimide and Cobalt(II) Acetate in Hexafluoropropan-2-ol
-
Efficient and highly selective catalytic conditions for the aerobic autoxidation of methylarenes to benzaldehydes, based on N-hydroxyphthalimide (NHPI) and cobalt(II) acetate in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), were developed. The sustainable conditions enable a multigram scale preparation of benzaldehyde derivatives in high efficiency and with excellent chemoselectivity (up to 99 % conversion and 98 % selectivity).
- Gaster, Eden,Kozuch, Sebastian,Pappo, Doron
-
supporting information
p. 5912 - 5915
(2017/05/12)
-
- One-pot two-step conversion of aromatic carboxylic acids and esters to aromatic aldehydes via indium-catalyzed reductive thioacetalization and desulfurization
-
Described herein is that a new approach to a one-pot two-step conversion of aromatic carboxylic acids/esters to aromatic aldehydes, in which indium(III) iodide effectively catalyzes both the first reductive thioacetalization of carboxylic acids and a subsequent desulfurization of the in-situ formed thioacetal intermediates leading to aldehydes.
- Sakai, Norio,Minato, Kohei,Ogiwara, Yohei
-
supporting information
p. 4563 - 4567
(2017/11/03)
-
- Selective reduction of carboxylic acids to aldehydes with hydrosilane: Via photoredox catalysis
-
The direct reduction of carboxylic acids to aldehydes with hydrosilane was achieved through visible light photoredox catalysis. The combination of both single electron transfer and hydrogen atom transfer steps offers a novel and convenient approach to selective reduction of carboxylic acids to aldehydes. The method also features mild conditions, high yields, broad substrate scope, and good functional group tolerance, such as alkyne, ester, ketone, amide and amine groups.
- Zhang, Muliang,Li, Nan,Tao, Xingyu,Ruzi, Rehanguli,Yu, Shouyun,Zhu, Chengjian
-
supporting information
p. 10228 - 10231
(2017/09/22)
-
- Dual Catalysis for the Aerobic Oxidation of Benzyl Alcohols – Nitric Acid and Fluorinated Alcohol
-
Benzyl alcohols were oxidized with oxygen to aldehydes in excellent yields with high selectivities at room temperature. Dual catalysis was operative with HNO3as the oxidant and precursor of the nitrogen oxides and with the use of 1,1,1,3,3,3-hexafluoro-2-propanol as a template catalyst and solvent. Fluorinated alcohols also increased the selectivity by inhibiting further oxidation to benzoic acids. Activation of nitric acid catalyzed aerobic oxidation by the fluorinated solvent made the use of 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) or a metal catalyst superfluous.
- Mo?ina, ?tefan,Stavber, Stojan,Iskra, Jernej
-
supporting information
p. 448 - 452
(2017/02/05)
-
- Ligandless Palladium-Catalyzed Reductive Carbonylation of Aryl Iodides under Ambient Conditions
-
Ligandless palladium-catalyzed reductive carbonylation of aryl iodides for the synthesis of aromatic aldehydes has been developed. This carbonylation process proceeded effectively even under ambient temperature and pressure. In addition, this method enables successive reductive carbonylation of diiodobenzenes to furnish dialdehydes in satisfactory yields. Finally, the nature of the active catalytic species is discussed.
- Han, Wei,Liu, Binbin,Chen, Junjie,Zhou, Qing
-
supporting information
p. 835 - 840
(2017/04/06)
-
- Combined production method for substituted benzaldehyde, substituted benzyl alcohol and substituted benzoic acid
-
The invention discloses a combined production method for substituted benzaldehyde, substituted benzyl alcohol and substituted benzoic acid. The method comprises the following steps: (1) oxidation: a step of continuously introducing substituted toluene, a catalyst and oxygen-contained gas into an oxidation reactor and carrying out reaction so as to obtain oxidation reaction liquid; (2) hydrolyzation: a step of allowing the oxidation reaction liquid to continuously enter a hydrolysis reactor, and continuously adding water into the hydrolysis reactor and carrying out reaction so as to obtain a hydrolysis reaction mixture; (3) liquid-liquid layering: a step of layering the hydrolysis reaction mixture so as to obtain an oil phase and an aqueous phase; and (4) separation of products: a step of subjecting the oil phase to distillation so as to respectively obtain incompletely-reacted substituted toluene, substituted benzyl alcohol and substituted benzaldehyde, and subjecting the aqueous phase to cooling, crystallizing and filtering so as to obtain filtrate and substituted benzoic acid. The combined production method provided by the invention has the advantages of high raw material conversion rate, few by-products, good selectivity of target products, greenness and environmental protection.
- -
-
Paragraph 0069; 0070
(2017/01/31)
-
- Controlled Reduction of Tertiary Amides to the Corresponding Alcohols, Aldehydes, or Amines Using Dialkylboranes and Aminoborohydride Reagents
-
Dialkylboranes and aminoborohydrides are mild, selective reducing agents complementary to the commonly utilized amide reducing agents, such as lithium aluminum hydride (LiAlH4) and diisobutylaluminum hydride (DIBAL) reagents. Tertiary amides were reduced using 1 or 2 equiv of various dialkylboranes. The reduction of tertiary amides required 2 equiv of 9-borabicyclo[3.3.1]nonane (9-BBN) for complete reduction to give the corresponding tertiary amines. One equivalent of sterically hindered disiamylborane reacts with tertiary amides to afford the corresponding aldehydes. Aminoborohydrides are powerful and selective reducing agents for the reduction of tertiary amides. Lithium dimethylaminoborohydride and lithium diisopropylaminoborohydride are prepared from n-butyllithium and the corresponding amine-borane. Chloromagnesium dimethylaminoborohydride (ClMg+[H3B-NMe2]-, MgAB) is prepared by the reaction of dimethylamine-borane with methylmagnesium chloride. Solutions of aminoborohydride reduce aliphatic, aromatic, and heteroaromatic tertiary amides to give the corresponding alcohol, amine, or aldehyde depending on the steric requirement of the tertiary amide and the aminoborohydride used.
- Bailey, Christopher L.,Joh, Alexander Y.,Hurley, Zefan Q.,Anderson, Christopher L.,Singaram, Bakthan
-
p. 3619 - 3628
(2016/05/24)
-
- Aldehyde and Ketone Synthesis by P450-Catalyzed Oxidative Deamination of Alkyl Azides
-
Heme-containing proteins have recently attracted increasing attention for their ability to promote synthetically valuable transformations not found in nature. Following the recent discovery that engineered variants of myoglobin can catalyze the direct conversion of organic azides into aldehydes, we investigated the azide oxidative deamination reactivity of a variety of hemoproteins featuring different heme coordination environments. Our studies show that although several heme-containing enzymes possess basal activity in this reaction, an engineered variant of the bacterial cytochrome P450 CYP102A1 constitutes a particularly efficient biocatalyst for promoting this transformation, and it exhibits a broad substrate scope along with high catalytic activity (up to 11 300 turnovers), excellent chemoselectivity, and enhanced reactivity toward secondary alkyl azides to yield ketones. Mechanistic studies and Michaelis–Menten analyses provided insight into the mechanism of the reaction and the impact of active-site mutations on the catalytic properties of the P450. Altogether, these studies demonstrate that engineered P450 variants represent promising biocatalysts for the synthesis of aryl aldehydes and ketones through the oxidative deamination of alkyl azides under mild reaction conditions.
- Giovani, Simone,Alwaseem, Hanan,Fasan, Rudi
-
p. 2609 - 2613
(2016/08/30)
-
- Oxygenation of Methylarenes to Benzaldehyde Derivatives by a Polyoxometalate Mediated Electron Transfer-Oxygen Transfer Reaction in Aqueous Sulfuric Acid
-
The synthesis of benzaldehyde derivatives by oxygenation of methylarenes is of significant conceptual and practical interest because these compounds are important chemical intermediates whose synthesis is still carried out by nonsustainable methods with very low atom economy and formation of copious amounts of waste. Now an oxygenation reaction with a 100% theoretical atom economy using a polyoxometalate oxygen donor has been found. The product yield is typically above 95% with no "overoxidation" to benzoic acids; H2 is released by electrolysis, enabling additional reaction cycles. An electrocatalytic cycle is also feasible. This reaction is possible through the use of an aqueous sulfuric acid solvent, in an aqueous biphasic reaction mode that also allows simple catalyst recycling and recovery. The solvent plays a key role in the reaction mechanism by protonating the polyoxometalate thereby enabling the activation of the methylarenes by an electron transfer process. After additional proton transfer and oxygen transfer steps, benzylic alcohols are formed that further react by an electron transfer-proton transfer sequence forming benzaldehyde derivatives. (Chemical Equation Presented).
- Sarma, Bidyut Bikash,Efremenko, Irena,Neumann, Ronny
-
p. 5916 - 5922
(2015/05/27)
-
- Activation and Oxidation of Mesitylene C-H Bonds by (Phebox)Iridium(III) Complexes
-
A pincer iridium(III) complex, (Phebox)Ir(OAc)2OH2 (1) (Phebox = 3,5-dimethylphenyl-2,6-bis(oxazolinyl)), selectively cleaves the benzylic C-H bond of mesitylene to form an isolable iridium mesityl complex, (Phebox)Ir(mesityl)(OAc) (3), in >90% yield. The trifluoroacetate analogue, (Phebox)Ir(OCOCF3)2OH2 (2), was synthesized to compare with complex 1 for C-H activation, and (Phebox)Ir(mesityl)(OCOCF3) (4) was synthesized by ligand exchange of complex 3. Both complexes 1 and 2 catalyze H/D exchange between mesitylene and D2O at 180 °C, exclusively at the benzylic position; 2 gave a higher turnover number (11 TO) than 1 (6 TO) in 12 h. Using d4-acetic acid as the source of deuterium, up to 92 turnovers of benzylic H/D exchange of mesitylene were obtained with complex 1. (Phebox)Ir(OCOCF3)2OH2 catalyzed the benzylic C-H oxidation of mesitylene using Ag2O as a terminal oxidant at 130 C, to form 3,5-dimethylbenzaldehyde and 3,5-dimethylbenzoic acid in 35% ± 4% yield (5.1 ± 0.6 TO). DFT calculations were used to investigate two possible pathways for the catalytic oxidation of mesitylene: (1) C-H activation followed by oxy-functionalization and (2) Ir-oxo formation followed by outer-sphere C-H hydroxylation. Results of calculations of the C-H activation pathway appear to be the more consistent with the experimental observations. (Chemical Equation Presented).
- Zhou, Meng,Johnson, Samantha I.,Gao, Yang,Emge, Thomas J.,Nielsen, Robert J.,Goddard, William A.,Goldman, Alan S.
-
supporting information
p. 2879 - 2888
(2015/06/30)
-
- Palladium-catalyzed synthesis of aldehydes from aryl halides and tert-butyl isocyanide using formate salts as hydride donors
-
An efficient one-pot palladium-catalyzed hydroformylation of aryl halides to produce aromatic aldehydes has been achieved, employing tert-butyl isocyanide as a C1 resource and formate salt as a hydride donor without any additional bases. Characterized by its mild reaction conditions, easy operation and lower toxicity, this reaction can tolerate a wide array of functional groups with moderate to excellent yields.
- Zhang, Ying,Jiang, Xiao,Wang, Jin-Mei,Chen, Jing-Lei,Zhu, Yong-Ming
-
p. 17060 - 17063
(2015/03/30)
-
- Reduction of Weinreb amides to aldehydes under ambient conditions with magnesium borohydride reagents Dedicated to the memory of Professor Sheldon Shore
-
Chloromagnesium dimethylaminoborohydride (ClMg+ [H3BNMe2]-, MgAB) is an analogue of the versatile lithium dialkylaminoborohydrides (LAB reagents), prepared by the reaction of dimethylamine-borane with methylmagnesium chloride. MgAB is a partial reducing agent for Weinreb amides under ambient conditions and is complementary to the commonly utilized lithium aluminum hydride (LiAlH4) and diisobutylaluminum hydride (DIBAL) reagents, while exhibiting enhanced chemoselectivity. To prevent over-reduction, the aldehyde products are readily isolated in good yields by forming the sodium bisulfite adducts. Aldehyde products can both be stored and later used as the bisulfite adducts, or can be regenerated from the bisulfite adducts by treatment with aqueous formaldehyde.
- Bailey, Christopher L.,Clary, Jacob W.,Tansakul, Chittreeya,Klabunde, Lucas,Anderson, Christopher L.,Joh, Alexander Y.,Lill, Alexander T.,Peer, Natalie,Braslau, Rebecca,Singaram, Bakthan
-
supporting information
p. 706 - 709
(2015/01/30)
-
- Efficient conversion of primary azides to aldehydes catalyzed by active site variants of myoglobin
-
The oxidation of primary azides to aldehydes constitutes a convenient but underdeveloped transformation for which no efficient methods are available. Here, we demonstrate that engineered variants of the hemoprotein myoglobin can catalyze this transformation with high efficiency (up to 8500 turnovers) and selectivity across a range of structurally diverse aryl-substituted primary azides. Mutagenesis of the 'distal' histidine residue was particularly effective in enhancing the azide oxidation reactivity of myoglobin, enabling these reactions to proceed in good to excellent yields (37-89%) and to be carried out at a synthetically useful scale. Kinetic isotope effect, isotope labeling, and substrate binding experiments support a mechanism involving heme-catalyzed decomposition of the organic azide followed by alpha hydrogen deprotonation to generate an aldimine which, upon hydrolysis, releases the aldehyde product. This work provides the first example of a biocatalytic azide-to-aldehyde conversion and expands the range of non-native chemical transformations accessible through hemoprotein-mediated catalysis.
- Giovani, Simone,Singh, Ritesh,Fasan, Rudi
-
p. 234 - 239
(2015/12/30)
-
- Improved Sommelet reaction catalysed by lanthanum triflate
-
An improved Sommelet reaction for the synthesis of araldehydes from benzyl halides and hexamethylenetetramine was achieved employing lanthanum triflate (3 mol%) as catalyst in water with sodium dodecyl sulfate (SDS, 2 wt%) as solubiliser. Good to excellent yields were obtained in most of the 18 examples.
- Xu, Wenhao,Su, Weike
-
p. 710 - 714
(2015/03/04)
-
- Preparation of silver-tungsten nanostructure materials for selective oxidation of toluene to benzaldehyde with hydrogen peroxide
-
We have developed a facile one-pot synthetic strategy to prepare Ag/WO3nanostructure materials with different morphologies using a cationic surfactant, cetyltrimethylammonium bromide. These materials were employed as catalysts in the direct synthesis of toluene to benzaldehyde using H2O2. The morphology of the Ag/WO3materials can be varied by changing the synthesis parameters. The size and shape of the Ag/WO3nanostructure catalyst has direct influence on the toluene conversion and benzaldehyde selectivity. The effect of different reaction parameters like reaction temperature, H2O2to toluene molar ratio, reaction time, and so forth have been studied in detail. The Ag/WO3catalyst with ~7 nm silver nanoparticles on the WO3nanorod with a diameter ~60 nm showed the best catalytic activity of 42% toluene conversion with 93% benzaldehyde selectivity. The catalyst did not show any leaching up to four reuses, showing the true heterogeneity of the catalyst. This journal is
- Ghosh, Shilpi,Acharyya, Shankha S.,Tripathi, Deependra,Bal, Rajaram
-
supporting information
p. 15726 - 15733
(2015/02/18)
-
- One step C-N bond formation from alkylbenzene and ammonia over Cu-modified TS-1 zeolite catalyst
-
A Cu doped TS-1 zeolite sample was applied to catalyze the formation of C-N bonds on both the ring and the side chain of toluene, as well as other alkylbenzenes. A yield of 3.4% of toluidine was obtained for the amination of toluene, with a 1.0% yield of nitrobenzene. Cyanobenzene was also obtained as the C-N bond product on the side chain with a yield of 1.0%. The selectivity for C-N bond formation was 52.4%. The catalyst promoted the formation of a hydroxylamine intermediate from ammonia and hydrogen peroxide, and then the instantaneously generated amino cation reacted with the substrate to form C-N bonds on both the ring and side chain. Cyanobenzene was produced from the dehydration of benzylamine, formed via the reaction of ammonia and toluene. The formation of C-N bonds on the ring had an ortho-orientation advantage for mono-substituted-benzenes. With the increase in the number of methyl substituents, the yield of the ring products decreased, which might be caused by steric hindrance. the Partner Organisations 2014.
- Xia, Sheng,Yu, Tianhua,Liu, Huihui,Li, Guiying,Hu, Changwei
-
p. 3108 - 3119
(2014/08/18)
-
- Palladium-catalyzed formylation of aryl halides with tert -butyl isocyanide
-
A novel palladium-catalyzed formylation of aryl halides with isocyanide in the presence of Et3SiH has been demonstrated, which provides a strategy toward important aldehydes with moderate to excellent yield. The advantage of this reaction includes milder conditions, convenient operation, lower toxicity, and wide functional group tolerance.
- Jiang, Xiao,Wang, Jin-Mei,Zhang, Ying,Chen, Zhong,Zhu, Yong-Ming,Ji, Shun-Jun
-
supporting information
p. 3492 - 3495
(2014/07/21)
-
- Cooperative catalysis of palladium nanoparticles and cobalt oxide support for formylation of aryl iodides under syngas atmosphere
-
Formylation of aryl iodides proceeded effectively in the presence of palladium nanoparticles on cobalt oxide under a syngas atmosphere to afford aldehydes up to 91% yield. A cooperative effect between palladium nanoparticles and cobalt species derived from the support was integral to efficient transformation. Both palladium and cobalt were revealed to exist as zero valent metals after H2 treatment from X-ray absorption near edge structure and X-ray diffraction spectra. The catalyst could be reused at least 7 times without significant loss of activity.
- Hamasaki, Akiyuki,Yasutake, Yutaro,Norio, Takafumi,Ishida, Tamao,Akita, Tomoki,Ohashi, Hironori,Yokoyama, Takushi,Honma, Tetsuo,Tokunaga, Makoto
-
p. 146 - 152
(2013/11/19)
-
- Aerobic oxidation of alcohols by using a completely metal-free catalytic system
-
A metal-free reaction system of air, NH4NO3(cat), 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)(cat), and H +(cat) is introduced as a simple, safe, inexpensive, efficient and chemoselective mediator for aerobic oxidation of various primary and secondary benzyl and alkyl alcohols, including those bearing oxidizable heteroatoms (N, S, O) to the corresponding aldehydes or ketones. Air oxygen under slight overpressure plays the role of the terminal oxidant, which is catalytically activated by redox cycles of nitrogen oxides released from a catalytic amount of NH4NO3 and cocatalyzed by TEMPO (nitroxyl radical compound), under acidic conditions, which are essential for an overall activation of the reaction system. The synthetic value of this reaction system and its green chemical profile was illustrated by a 10 g scale-up experiment, performed in an open-air system by using a renewable and reusable polymer-supported form of TEMPO (OXYNITROXS100). The reaction solvent was recovered by distillation under atmospheric pressure, and the pure final product was isolated under reduced pressure; the acid activators (HCl or H 2SO4) were recovered as ammonium salts. A metal-free reaction system of air/NH4NO3(cat)/TEMPO (cat)/H+(cat) is introduced as a simple, safe, inexpensive, efficient and chemoselective mediator for aerobic oxidation of various primary and secondary benzyl, alkyl and allyl alcohols, including those bearing oxidizable heteroatoms (N, S, O) to the corresponding aldehydes or ketones. Copyright
- Prebil, Rok,Stavber, Gaj,Stavber, Stojan
-
supporting information
p. 395 - 402
(2014/01/23)
-
- Aerobic Oxidation of Alcohols by Using a Completely Metal-Free Catalytic System
-
A metal-free reaction system of air, NH4NO3(cat), 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)(cat), and H+(cat) is introduced as a simple, safe, inexpensive, efficient and chemoselective mediator for aerobic oxidation of various primary and secondary benzyl and alkyl alcohols, including those bearing oxidizable heteroatoms (N, S, O) to the corresponding aldehydes or ketones. Air oxygen under slight overpressure plays the role of the terminal oxidant, which is catalytically activated by redox cycles of nitrogen oxides released from a catalytic amount of NH4NO3 and cocatalyzed by TEMPO (nitroxyl radical compound), under acidic conditions, which are essential for an overall activation of the reaction system. The synthetic value of this reaction system and its green chemical profile was illustrated by a 10 g scale-up experiment, performed in an open-air system by using a renewable and reusable polymer-supported form of TEMPO (OXYNITROXS100). The reaction solvent was recovered by distillation under atmospheric pressure, and the pure final product was isolated under reduced pressure; the acid activators (HCl or H2SO4) were recovered as ammonium salts.
- Prebil, Rok,Stavber, Gaj,Stavber, Stojan
-
supporting information
p. 395 - 402
(2015/10/05)
-
- Solvent-free selective oxidation of C-H bonds of toluene and substituted toluene to aldehydes by vanadium-substituted polyoxometalate catalyst
-
A novel homogeneous vanadium-substituted polyoxometalate catalyst of [n-Bu4N]3H3[PW9V3O 40] showed good catalytic activity for the activation of CH bonds of toluene and substituted toluene with TBHP (70% aq) under solvent-free conditions. Under the optimal conditions, a 65% yield of benzaldehyde and a TON of 5221 were obtained over this catalyst at 343 K. This catalyst also showed good conversion and selectivity for the oxidation of a series of substituted toluene. The vanadium-substituted Keggin-POM was not decomposed to some species upon the treatment of 530-fold of TBHP by IR characterization. A free radical mechanism was proposed based on the experimental results and the literature supports.
- Ma, Baochun,Zhang, Zhenxin,Song, Wenfeng,Xue, Xiaoling,Yu, Yongze,Zhao, Zhensheng,Ding, Yong
-
p. 152 - 158
(2013/04/10)
-
- Palladium-catalyzed reduction of carboxylic acids to aldehydes with hydrosilanes in the presence of pivalic anhydride
-
A palladium catalyst system that allows the reduction of carboxylic acids to the corresponding aldehydes with hydrosilanes as reducing agent and pivalic anhydride as an indispensable reagent has been developed. A simple mixture of commercially available bis(dibenzylideneacetone)palladium(0) [Pd(dba) 2], tri(para-tolyl)phosphane and methylphenylsilane realized the reduction of various aliphatic carboxylic acids as well as benzoic acids to aldehydes in good to high yields. Copyright
- Fujihara, Tetsuaki,Cong, Cong,Terao, Jun,Tsuji, Yasushi
-
supporting information
p. 3420 - 3424
(2013/12/04)
-
- 4-N,N-dimethylaminopyridine promoted selective oxidation of methyl aromatics with molecular oxygen
-
4-N,N-Dimethylaminopyridine (DMAP) as catalyst in combination with benzyl bromide was developed for the selective oxidation of methyl aromatics. DMAP exhibited higher catalytic activity than other pyridine analogues, such as 4-carboxypyridine, 4-cyanopyridine and pyridine. The sp3 hybrid carbon-hydrogen (C-H) bonds of different methyl aromatics were successfully oxygenated with molecular oxygen. The real catalyst is due to the formation of a pyridine onium salt from the bromide and DMAP. The onium salt was well characterized by NMR and the reaction mechanism was discussed.
- Zhang, Zhan,Gao, Jin,Wang, Feng,Xu, Jie
-
experimental part
p. 3957 - 3968
(2012/07/27)
-
- Remarkable effect of PEG-1000-based dicationic ionic liquid for N-Hydroxyphthalimide-catalyzed aerobic selective oxidation of alkylaromatics
-
PEG 1000-based functional dicationic acidic ionic liquid (PEG 1000-DAIL) was used for the first time as the reaction solvent for the N-Hydroxyphthalimide (NHPI)-cobalt acetate(Co(OAc)2) catalyzed aerobic oxidations of alkylaromatics to the corresponding acids. It enhanced the efficient catalytic ability of NHPI: 99.9 % conversion of toluene with 99.5 % selectivity for benzoic acid could be obtained at 80 °C in 10 h and ethylbenzene was selectively oxidized to benzoic acid. Several alkylaromatics were efficiently oxidized to their corresponding acids under mild conditions. For substituted toluene, the conversions of substrates and the selectivity of products was affected by the position and kind of substituted groups, respectively. Both the catalyst and PEG1000-DAIL could be reused at least eight times without significantly decreasing the catalytic activity.
- Lu, Tingting,Lu, Ming,Yu, Wang,Liu, Zhongjie
-
p. 277 - 282
(2013/01/15)
-
- Straightforward synthesis of aromatic imines from alcohols and amines or nitroarenes using an impregnated copper catalyst
-
The impregnated copper on magnetite catalyst is a versatile system for the synthesis of imines starting from alcohols and amines. This catalyst does not require any type of expensive and difficult to handle organic ligand or typical transition metals, and provides excellent yields achievable under mild reaction conditions. Moreover, the catalyst is very easy to remove from the reaction medium by simply using a magnet. The one-pot process of dehydrogenation of alcohols in the presence of aniline followed by aqueous hydrolysis gave pure alcohols in excellent yields. In addition to amines, nitroarenes could be used as the nitrogen-containing reagent. In the case of primary amines the expected imines were successfully prepared under similar reaction conditions. The impregnated copper on magnetite catalyst is a versatile system for the synthesis of imines starting from alcohols and amines or nitroarenes. A similar synthesis of imines was accomplished using only primary amines. This catalyst avoids the use of expensive organic ligands and other transition metals while enabling excellent yields under mild reaction conditions. Copyright
- Perez, Juana M.,Cano, Rafael,Yus, Miguel,Ramon, Diego J.
-
p. 4548 - 4554
(2012/11/07)
-
- Manganese oxide promoted liquid-phase aerobic oxidative amidation of methylarenes to monoamides using ammonia surrogates
-
In the presence of amorphous MnO2, various methylarenes (even with two or more methyl groups) could be selectively converted into the corresponding primary monoamides in moderate to high yields. The observed catalysis was truly heterogeneous, and the retrieved amorphous MnO2 catalyst could be reused without an appreciable loss of its catalytic performance. Copyright
- Wang, Ye,Yamaguchi, Kazuya,Mizuno, Noritaka
-
supporting information; experimental part
p. 7250 - 7253
(2012/08/28)
-
- A heterogenized vanadium oxo-aroylhydrazone catalyst for efficient and selective oxidation of hydrocarbons with hydrogen peroxide
-
A hydrazone Schiff base ligand derived from salicylaldehyde and benzhydrazide has been synthesized and reacted with vanadium(IV) leading to the corresponding vanadium(V) complex. The complex has been anchored on the surface of functionalized silica gel by N,O-coordination to the covalently Si-O bound modified salicylaldiminato ligand. The supported complex has been evaluated as a catalyst for hydrocarbon oxidation with hydrogen peroxide in acetonitrile. The heterogeneous system proved to be an efficient catalyst and was able to activate hydrogen peroxide toward the oxidation of alkenes, alkanes, benzene, and alkylaromatic compounds with more than 2,500 h-1 activity. Springer Science+Business Media B.V. 2011.
- Monfared, Hassan Hosseini,Abbasi, Vahideh,Rezaei, Adineh,Ghorbanloo, Massomeh,Aghaei, Alireza
-
experimental part
p. 85 - 92
(2012/08/28)
-
- Direct arylation of unactivated aromatic C-H bonds catalyzed by a stable organic radical
-
A stable zwitterionic radical can catalyze direct arylation of unactivated aromatic C-H bonds via a chain homolytic aromatic substitution mechanism in the presence of potassium tert-butoxide.
- Yong, Guo-Ping,She, Wen-Long,Zhang, Yi-Man,Li, Ying-Zhou
-
supporting information; experimental part
p. 11766 - 11768
(2011/11/29)
-
- Beyond click-chemistry: Transformation of azides with cyclopentadienyl ruthenium complexes
-
The cyclopentadienyl Ru complexes Cp*RuCl(cod) (cod = 1,5-cyclooctadiene), Cp*RuCl(PPh3)2, and [CpRuCl2]2 (Cp = η5-1-methoxy-2,4-di-tert- butyl-3-neopentylcyclopentadienyl) are able to catalyze the decomposition of benzyl azides to give 1,3,5-triphenyl-2,4-diazapenta-1,4-diene ("hydrobenzamide"), benzyl-benzylideneamine, and benzonitrile. Reactions with the catalyst precursor [CpRuCl2]2 are particularly fast and give hydrobenzamide with high selectivity. A similar coupling reaction is observed for other benzylic azides but not for (2-azidoethyl)benzene and ethyl-4-azidobutanoate. If the reactions are performed in the presence of water, benzylic azides are converted into aldehydes. Mononuclear tetrazene complexes are formed in stoichiometric reactions of [CpRuCl2]2 with benzyl azide and (2-azidoethyl)benzene.
- Risse, Julie,Scopelliti, Rosario,Severin, Kay
-
experimental part
p. 3412 - 3418
(2011/08/08)
-