- Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement
-
Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.
- Cheng, Mu-Jeng,Kardile, Rahul Dadabhau,Kuo, Tung-Chun,Liu, Rai-Shung,More, Sayaji Arjun
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p. 5506 - 5511
(2021/07/31)
-
- KDS2010, a Newly Developed Reversible MAO-B Inhibitor, as an Effective Therapeutic Candidate for Parkinson’s Disease
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Monoamine oxidase-B (MAO-B) is a well-established therapeutic target for Parkinson’s disease (PD); however, previous clinical studies on currently available irreversible MAO-B inhibitors have yielded disappointing neuroprotective effects. Here, we tested the therapeutic potential of KDS2010, a recently synthesized potent, selective, and reversible MAO-B inhibitor in multiple animal models of PD. We designed and synthesized a series of α-aminoamide derivatives and found that derivative KDS2010 exhibited the highest potency, specificity, reversibility, and bioavailability (> 100%). In addition, KDS2010 demonstrated significant neuroprotective and anti-neuroinflammatory efficacy against nigrostriatal pathway destruction in the mouse MPTP model of parkinsonism. Treatment with KDS2010 also alleviated parkinsonian motor dysfunction in 6-hydroxydopamine-induced and A53T mutant α-synuclein overexpression rat models of PD. Moreover, KDS2010 showed virtually no toxicity or side effects in non-human primates. KDS2010 could be a next-generation therapeutic candidate for PD.
- Nam, Min-Ho,Park, Jong-Hyun,Song, Hyo Jung,Choi, Ji Won,Kim, Siwon,Jang, Bo Ko,Yoon, Hyung Ho,Heo, Jun Young,Lee, Hyowon,An, Heeyoung,Kim, Hyeon Jeong,Park, Sun Jun,Cho, Doo-Wan,Yang, Young-Su,Han, Su-Cheol,Kim, Sangwook,Oh, Soo-Jin,Jeon, Sang Ryong,Park, Ki Duk,Lee, C. Justin
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p. 1729 - 1747
(2021/10/08)
-
- Pd-Catalysed Suzuki-Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides
-
The Suzuki-Miyaura coupling reaction of electron-poor aryl chlorides in the synthesis of crop protection-relevant active ingredients in water is disclosed. Optimisation of the reaction conditions allowed running the reaction with 50 ppm of Pd-catalyst loading without an additional organic solvent in the cross-coupling reaction step in short reaction times. The system was optimised for the initial cross-coupling step of the large scale produced fungicides Boscalid, Fluxapyroxad and Bixafen up to 97% yield. It is also shown that the Suzuki-Miyaura reaction can be easily scaled up to 50 g using a simple product separation and purification using environmentally benign solvents in the work-up. To show the usability of this method, it was additionally applied in the three-step synthesis of the desired active ingredients.
- Goetz, Roland,Hashmi, A. Stephen K.,Orecchia, Patrizio,Petkova, Desislava Slavcheva,Rominger, Frank,Schaub, Thomas
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supporting information
p. 8169 - 8180
(2021/11/01)
-
- Solvent Effects on the Selectivity of Palladium-Catalyzed Suzuki-Miyaura Couplings
-
The use of polar solvents MeCN or dimethylformamide (DMF) was previously shown to induce a selectivity switch in the Pd/PtBu3-catalyzed Suzuki-Miyaura coupling of chloroaryl triflates. This phenomenon was attributed to the ability of polar solvents to stabilize anionic transition states for oxidative addition. However, we demonstrate that selectivity in this reaction does not trend with solvent dielectic constant. Unlike MeCN and DMF, water, alcohols, and several polar aprotic solvents such as MeNO2, acetone, and propylene carbonate provide the same selectivity as nonpolar solvents. These results indicate that the role of solvent on the selectivity of Suzuki-Miyaura couplings may be more complex than previously envisioned. Furthermore, this observation has the potential for synthetic value as it greatly broadens the scope of solvents that can be used for chloride-selective cross coupling of chloroaryl triflates.
- Reeves, Emily K.,Bauman, Olivia R.,Mitchem, Gunner B.,Neufeldt, Sharon R.
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p. 406 - 409
(2019/09/13)
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- (N-Heterocyclic carbene) ion-pair palladium complexes: Suzuki–Miyaura cross-coupling studies in neat water under mild conditions
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The synthesis and characterization of a series of (N-heterocyclic carbene)PdCl3?(NMe3H)+ ion-pair complexes are presented. Applying the quaternary ammonium salt as the function with NHC–Pd(II) complexes yields the new ion-pair complexes. The NHC–Pd(II) ion-pair complexes work well by undergoing the Suzuki–Miyaura reaction with aryl chloride substrates in water under mild conditions in air at room temperature. Twenty products resulting from Suzuki–Miyaura coupling reactions carried out in the presence of the new NHC–Pd(II) ion-pair complex under mild optimal conditions were examined to determine the optimum yields.
- Chen, Ming-Tsz,Lin, Yu-Hsuan,Jian, Kun-Han
-
-
- Salicylaldehyde-stabilized palladium nanoparticles for highly efficient suzuki-miyaura reaction at room temperature
-
Pd-catalyzed Suzuki-Miyaura cross-coupling reactions promoted by simple and commercial salicylaldehyde-based ligands were investigated. The effect of the ligands was evaluated and the reaction conditions were optimized. Moreover, the physical nature of the palladium was determined by TEM analysis and poison tests. It demonstrated that this catalytic system can be reused for ten consecutive runs and showed excellent activities toward aryl bromides with arylboronic acids at room temperature in air.
- Zhou, Zhen,Cao, Gao,Liu, Ning
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supporting information
p. 547 - 550
(2019/06/11)
-
- CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE
-
Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.
- -
-
Paragraph 00293-00295
(2019/06/11)
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- N-Heterocyclic Carbene Ligand-Controlled Chemodivergent Suzuki-Miyaura Cross Coupling
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Two N-heterocyclic carbene ligands provide orthogonal chemoselectivity during the Pd-catalyzed Suzuki-Miyaura (SM) cross-coupling of chloroaryl triflates. The use of SIPr [SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene] leads to selective cross-coupling at chloride, while the use of SIMes [SIMes = 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene] provides selective coupling at triflate. With most chloroaryl triflates and arylboronic acids, ligand-controlled selectivity is high (≥10:1). The scope of this methodology is significantly more general than previously reported methods for selective SM coupling of chloroaryl triflates using phosphine ligands. Density functional theory studies suggest that palladium's ligation state during oxidative addition is different with SIMes compared to SIPr.
- Reeves, Emily K.,Humke, Jenna N.,Neufeldt, Sharon R.
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p. 11799 - 11812
(2019/10/11)
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- PdII Immobilized on Ferromagnetic Multi-Walled Carbon Nanotubes Functionalized by Aminated 2-Chloroethylphosphonic Acid with S -Methylisothiourea (FMMWCNTs@CPA@SMTU@PdII NPs) Applied as a Highly Efficient and Recyclable Nanostructured Catalyst for Suzuki-Miyaura and Mizoroki-Heck Cross-Coupling Reactions in Solvent-Free Conditions
-
The new ferromagnetic nanostructured FMMWCNTs@CPA@SMTU@PdII NPs (IV) as an eco-friendly heterogeneous nanocatalyst with a particle size of ~20-30 nm reported earlier by our group has been found to be very effective for Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions at ambient temperature. The procedure has been applied for a wide range of aryl halides, arylboronic acids, and alkenes. The magnetic separation by an external magnetic field, mild reaction conditions, and catalyst reusability up to four times without significant decrease in catalytic activity (reduced catalytic activity from 11 to 18 % in the fifth, sixth, and seventh cycles) made the present method sustainable and economically viable for C-C cross-coupling reactions.
- Ghasemzadeh, Maryam Sadat,Akhlaghinia, Batool
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p. 674 - 692
(2019/07/12)
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- Synthesis and characterization of Pd-γ-Fe2O3 nanocomposite and its application as a magnetically recyclable catalyst in ligand-free Suzuki-Miyaura reaction in water
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A novel redox-driven method to synthesize Pd-γ-Fe2O3 nanocomposite from Fe3O4 and PdCl2 under modified hydrothermal technique has been developed. The synthesized nanocomposite was characterized by XRD, FT-IR, XPS, FESEM, TEM and EDX to understand the composition as well as morphology. The Pd-γ-Fe2O3 nanocomposite was found to show excellent catalytic activity towards Suzuki-Miyaura cross-coupling reactions in water without the assistance of ligands, organic solvents or phase transfer catalysts. A wide range of functional substitutions in aryl halide as well as arylboronic acid moieties is tolerated in the developed protocol. The nanocatalyst can be recovered magnetically, and reused up to six cycles without significant loss in its catalytic activity.
- Paul, Dipankar,Rudra, Siddheswar,Rahman, Prabin,Khatua, Snehadrinarayan,Pradhan, Mukul,Chatterjee, Paresh Nath
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supporting information
p. 96 - 102
(2018/07/25)
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- A new diphosphine-carbonyl complex of ruthenium: an efficient precursor for C-C and C-N bond coupling catalysis
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Reaction of 1,2-bis(diphenylphosphino)benzene (dppbz) with [{Ru(CO)2Cl2}n] affords [Ru(dppbz)(CO)2Cl2], where the two carbonyls are mutually cis and the two chlorides are trans. The molecular structure of [Ru(dppbz)(CO)2Cl2], has been determined by X-ray crystallography, and the stability of the different available stereoisomers has been computationally evaluated. [Ru(dppbz)(CO)2Cl2] has been found to serve as an excellent pre-catalyst for catalytic Suzuki-type C-C coupling and Buchwald-type C-N coupling reactions.
- Mukherjee, Aparajita,Hrovat, David A.,Richmond, Michael G.,Bhattacharya, Samaresh
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p. 10264 - 10272
(2018/08/06)
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- Discovery of selective protein arginine methyltransferase 5 inhibitors and biological evaluations
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Protein arginine methyltransferase 5 (PRMT5) is an important protein arginine methyltransferase that catalyzes the symmetric dimethylation of arginine resides on histones or non-histone substrate proteins. It has been thought as a promising target for many diseases, particularly cancer. Despite the potential applications of PRMT5 inhibitors in cancer treatment, very few of PRMT5i have been publicly reported. In this investigation, virtual screening and structure–activity relationship studies were carried out to discover novel PRMT5i, which finally led to the identification of a number of new PRMT5i. The most active compound, P5i-6, exhibited a considerable inhibitory potency against PRMT5 with an IC50 value of 0.57?μm, and a high selectivity for PRMT5 against other tested PRMTs. It displayed a very good antiviability activity against two colorectal cancer cell lines, HT-29 and DLD-1, and one hepatic cancer cell line, HepG2, in a sensitivity assay against 36 different cancer cell lines. Western blot assays indicated that P5i-6 selectively inhibited the symmetric dimethylations of H4R3 and H3R8 in DLD-1 cells. Overall, P5i-6 could be used as a chemical probe to investigate new functions of PRMT5 in biology and also served as a good lead compound for the development of new PRMT5-targeting therapeutic agents.
- Ji, Sen,Ma, Shuang,Wang, Wen-Jing,Huang, Shen-Zhen,Wang, Tian-Qi,Xiang, Rong,Hu, Yi-Guo,Chen, Qiang,Li, Lin-Li,Yang, Sheng-Yong
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p. 585 - 598
(2017/04/06)
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- SYNTHESES OF METAL HETEROCYCLIC CARBENE ENOLATES AS COUPLING REACTIONS CATALYSTS
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The invention relates to the synthesis methods of N-heterocyclic carbene NHCE metal complexes and their catalytic activities in carbon-carbon coupling reactions.
- -
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Page/Page column 18; 20; 21; 32
(2017/07/01)
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- A self-assembled bisoxazoline/Pd composite microsphere as an excellent catalyst for Suzuki-Miyaura coupling reactions
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A palladium complex based on a novel oxazoline, a solid microsphere catalyst, was successfully prepared. The structure and composition of the solid catalyst were characterized by SEM, 1H NMR, TGA and FT-IR. This catalyst exhibits high catalytic activity for Suzuki-Miyaura cross-coupling reactions of various aryl halides and arylboronic acids in aqueous media. Moreover, the catalyst shows outstanding stability and reusability, and it can be recovered simply and effectively and reused eight times without any activity decrease.
- Wang, Junke,Zong, Yingxiao,Wang, Xicun,Hu, Yulai,Yue, Guoren,Pan, Yi
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supporting information
p. 967 - 973
(2016/02/27)
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- Probing the Azaaurone Scaffold against the Hepatic and Erythrocytic Stages of Malaria Parasites
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The potential of azaaurones as dual-stage antimalarial agents was investigated by assessing the effect of a small library of azaaurones on the inhibition of liver and intraerythrocytic lifecycle stages of the malaria parasite. The whole series was screened against the blood stage of a chloroquine-resistant Plasmodium falciparum strain and the liver stage of P. berghei, yielding compounds with dual-stage activity and sub-micromolar potency against erythrocytic parasites. Studies with genetically modified parasites, using a phenotypic assay based on the P. falciparum Dd2-ScDHODH line, which expresses yeast dihydroorotate dehydrogenase (DHODH), showed that one of the azaaurone derivatives has the potential to inhibit the parasite mitochondrial electron-transport chain. The global urgency in finding new therapies for malaria, especially against the underexplored liver stage, associated with chemical tractability of azaaurones, warrants further development of this chemotype. Overall, these results emphasize the azaaurone chemotype as a promising scaffold for dual-stage antimalarials.
- Carrasco, Marta P.,Machado, Marta,Gon?alves, Lídia,Sharma, Moni,Gut, Jiri,Lukens, Amanda K.,Wirth, Dyann F.,André, Vania,Duarte, Maria Teresa,Guedes, Rita C.,dos Santos, Daniel J. V. A.,Rosenthal, Philip J.,Mazitschek, Ralph,Prudêncio, Miguel,Moreira, Rui
-
supporting information
p. 2194 - 2204
(2016/10/19)
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- An imidazolium ionic compound-supported palladium complex as an efficient catalyst for Suzuki-Miyaura reactions in aqueous media
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A water soluble and efficient ionic compound-supported palladium complex was prepared. The structure and composition of the complex was characterized by FT-IR, NMR, ICP-OES and mass spectrometry. The complex exhibits high catalytic activity for Suzuki-Miyaura reactions in aqueous media. Moreover, the catalyst shows outstanding stability and reusability, and it can be recovered simply and effectively and reused six times without much activity decrease.
- Zong, Yingxiao,Wang, Junke,He, Yubi,Yue, Guoren,Wang, Xicun,Pan, Yi
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p. 89621 - 89626
(2016/10/03)
-
- Compounds
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Pyrimidone compounds of formula (I): are inhibitors of the enzyme Lp-PLA2 and are of use in treating atherosclerosis.
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Page/Page column 14
(2016/05/11)
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- Synthesis, structure and catalytic applications of octahedral nickel(II) benzoylhydrazone complex: Suzuki-Miyaura cross-coupling reaction of aryl bromides with arylboronic acid
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A simple route for the synthesis of a new octahedral nickel(II) complex (1) containing 4-chloro-benzoic acid pyridin-2-ylmethylene-hydrazide ligand (HL, where H represents the dissociable proton) has been described. The characterization of the complex having the formula [Ni(μ3-O,N,N-L)2] has been established by elemental analysis, ESI-MS, spectral methods and single crystal X-ray crystallography. Further, the new complex was found to act as an active homogeneous catalyst for the Suzuki-Miyaura reaction of substituted aryl bromides (mono and dibromides) with various arylboronic acids having different electronic effects under optimized conditions of solvent, base and catalyst loading. The biphenyl and triphenyl derivatives were obtained in moderate to excellent isolated yields.
- Suganthy, Pandimuni Kalpaga,Prabhu, Rupesh Narayana,Sridevi, Venugopal Shanmugham
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p. 127 - 132
(2016/06/01)
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- Destruction and Construction: Application of Dearomatization Strategy in Aromatic Carbon-Nitrogen Bond Functionalization
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The formation of carbon-carbon bonds through the functionalization of aromatic carbon-nitrogen bonds is a highly attractive synthetic strategy in the synthesis of aromatic molecules. In this paper, we report a novel aromatic carbon-nitrogen bond functionalization reaction by using a simple dearomatization strategy. Through this process para-substituted anilines serve as a potential aryl source in the construction of a range of functionalized aromatic molecules, such as quaternary carbon centers, α-keto esters, and aldehydes.
- Wang, Shuo-En,Wang, Linfei,He, Qiuqin,Fan, Renhua
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p. 13655 - 13658
(2015/11/11)
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- Development of unimolecular tetrakis(piperidin-4-ol) as a ligand for Suzuki-Miyaura cross-coupling reactions: Synthesis of incrustoporin and preclamol
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Abstract A domino aza-Cope/aza-Prins cascade enabled the synthesis of a new class of 4-hydroxypiperidine-appended mono, bis, tris, and tetrakis unimolecular compounds that served as efficient ligands to catalyze Suzuki-Miyaura cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields. The ligands were also capable of catalyzing the Heck-Mizoroki reaction. As an application, the Suzuki-Miyaura coupling reaction was used in the synthesis of incrustoporin, its analogs, and the drug molecule preclamol. A domino aza-Cope/aza-Prins cascade enabled the synthesis of a new class of 4-hydroxypiperidine-appended mono-, bis-, tris-, and tetrakis-unimolecular compounds that served as efficient ligands to catalyze Suzuki-Miyaura cross-coupling reactions under aerobic conditions. Various biaryls, terphenyls, and heterocyclic biphenyls were obtained in good to excellent yields.
- Nallasivam, Jothi L.,Fernandes, Rodney A.
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p. 3558 - 3567
(2015/06/08)
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- O-Aryloxime ether analogues as novel and efficient ligands for palladium-catalyzed Suzuki-Miyaura coupling in water
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O-Aryloxime ether analogues L1-L3 were studied as ligands in palladium-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl bromides and aryl boronic acids in water at room temperature. Reaction conditions for the cross-coupling were optimized using PdCl2 and Pd(OAc)2 under aerobic condition. From the three electronically diverse O-aryloxime ether ligands studied herein, the use of 1-phenyl-ethanone O-(4-chloro-phenyl)-oxime L2 exhibits the best catalytic system in the presence of K2CO 3 as the base and TBAB as the promoter.
- Mondal, Manoj,Bora, Utpal
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p. 3038 - 3040
(2014/05/20)
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- Room-temperature Suzuki-Miyaura reaction catalyzed by palladium nanoparticles in lactate-anion ionic liquid
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A palladium nanoparticle catalyst (PdNPs[Bmim]Lac) has been prepared by a simple, mild and efficient chemical approach using 1-butyl-3-methylimidazolium lactate ([Bmim]Lac) ionic liquid) as a stabilizer. This catalyst exhibits excellent activity, stability, recyclability and simple manipulation in Suzuki-Miyaura reactions at room temperature in air.
- Wang, Furong,Tang, Sisi,Ma, Hao,Wang, Lefu,Li, Xuehui,Yin, Biaolin
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p. 1225 - 1232
(2015/02/02)
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- AZOLE HETEROCYCLIC COMPOUND, PREPARATION METHOD, PHARMACEUTICAL COMPOSITION AND USE
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The present invention relates to the filed of pharmarcutical chemistry, and in particular, to a novel class of azole compounds represented by general formula (I), (II) or (III) amd a preparation method thereof, a pharmarcutical composition with the compounds as active components, and a use of the azole compounds and the pharmarcutical composition in the preparation of a medicament for treatment of diseases associated with Lp-PLA2 enzyme activities, wherein each substituent is as deinfed in the specifictaion.
- -
-
Paragraph 0135; 0136
(2014/05/20)
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- AZOLE HETEROCYCLIC COMPOUND, PREPARATION METHOD, PHARMACEUTICAL COMPOSITION AND USE
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The present invention relates to the field of pharmaceutical chemistry, and in particular, to a novel class of azole compounds represented by general formula (I), (II) or (III) and a preparation method thereof, a pharmaceutical composition with the compounds as active components, and a use of the azole compounds and the pharmaceutical composition in the preparation of a medicament for treatment of diseases associated with Lp-PLA2 enzyme activities, wherein each substituent is as defined in the specification.
- -
-
Paragraph 0471; 0472; 0481; 0482
(2014/06/25)
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- Nanoparticulate palladium catalyst stabilized by supported on feather keratin for Suzuki coupling reaction
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Palladium nanoparticles supported in a feather keratin matrix were efficient catalyst for the coupling reactions of aryl bromides with arylboronic acid in aqueous medium under mild reaction conditions. The biopolymer-based catalyst demonstrated excellent activity for substrates with a wide range of functional groups. The product biaryls were precipitated from the reaction mixture with good to excellent yields and purities. The catalyst was recovered from the reaction solution easily by simple filtration, and can be reused at least seven times.
- Ma, Hengchang,Bao, Zhikang,Han, Guobin,Yang, Ningning,Xu, Yufei,Yang, Zengming,Cao, Wei,Ma, Yuan
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p. 578 - 584
(2013/08/25)
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- α-Hydroxyimine palladium complexes: Synthesis, molecular structure, and their activities towards the Suzuki-Miyaura cross-coupling reaction
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An activity-promoting strategy for phosphine-free catalytic systems is presented in this study. The strategy is based on a series of non-conjugated N,O ligands with bulky substituents, [Ar-NC(R)-(R)C(CH3)OH] (L1, R = Acenaphthyl, Ar = 2,6-diiso
- Tang, Xiao,Huang, Ying-Tang,Liu, Huan,Liu, Rui-Zhi,Shen, Dong-Sheng,Liu, Ning,Liu, Feng-Shou
-
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- Synthesis, characterization and catalytic activity of palladium complexes with α-imino-amidos ligands
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In the present work, a series of steric substituted α-imino-amido palladium complexes, {[Ar-NC(CH3)-C(CH3)(R)-NH-Ar] PdCl2} (C1, R = Me, Ar = 2,6-dimethylphenyl; C2, R = Me, Ar = 2,6-diisopropylphenyl; C3, R = CH2Ph, Ar = 2,6-dimethylphenyl; C4, R = CH2Ph, Ar = 2,6-diisopropylphenyl), were synthesized and characterized. The structures of palladium complexes C3 and C4 were elucidated by X-ray diffraction. These bidentate nitrogen ligands were applied in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. The effect of ligand substitution as well as reaction conditions on catalytic activity was evaluated. Under the optimization process, the less bulky and electron-donating ligand were successfully used to catalyze the reaction of a variety of aryl bromides and chlorides with arylboronic acids, giving the desired biaryl products in high yields.
- Cao, Gao,Yang, Hai-Qing,Luo, Bao-Tian,Liu, Feng-Shou
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p. 158 - 165
(2013/10/01)
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- Efficient pyridylbenzamidine ligands for palladium-catalyzed Suzuki-Miyaura reaction
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A series of pyridylbenzamidine ligands were applied in palladium-catalyzed Suzuki-Miyaura reactions and the effect of ligand on catalytic properties was evaluated. Under the optimization conditions, the bulky and electron-donating nitrogen donor ligands were successfully used to catalyze the reaction of a variety of aryl bromides and aryl chlorides with arylboronic acid, giving the desired products in moderate to high yields. Copyright
- Huang, Ying-Tang,Tang, Xiao,Yang, Yi,Shen, Dong-Sheng,Tan, Cheng,Liu, Feng-Shou
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p. 701 - 706
(2013/02/22)
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- Efficient salicylaldimine ligands for a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction
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A series of salicylaldimine ligands were designed to promote palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. After a screening process, a ligand with a bulky 2,4-di-tert-butyl substituent on the salicyaldehyde backbone and cyclohexylamine moiety was found to serve as a good combination for this reaction in aqueous solutions of DMF. The protocol demonstrated a significant advance in the efficiency of the cross-coupling of aryl bromides and aryl chlorides with arylboronic acids to produce the desired biaryl products. Copyright 2012 John Wiley & Sons, Ltd. A systematic investigation on the effects of steric and electronic substituted salicylaldimine ligands and reaction conditions were tested in a Suzuki-Miyaura cross-coupling reaction. It demonstrated a significant advance in the efficiency of the cross-coupling of aryl bromides and aryl chlorides with arylboronic acids to produce the desired biaryl products. Copyright
- Liu, Feng-Shou,Huang, Ying-Tang,Lu, Chao,Shen, Dong-Sheng,Cheng, Tao
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experimental part
p. 425 - 429
(2012/09/22)
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- A novel one-pot synthesis of biaryl derivatives by sequential strategies via Suzuki coupling/Knoevenagel condensation in aqueous medium at room temperature
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A novel one-pot synthesis of biaryl derivatives has been developed starting from bromobenzaldehyde and phenylboronic acid in the presence of activated methylene compounds via sequential Suzuki coupling/Knoevenagel condensation in aqueous isopropanol medium at room temperature. Significantly, this strategy afforded a straightforward and efficient approach to construct original biaryls in which a new carbon double bond bound to activated moieties such as nitrile, ester and amide is formed from three simple substrates in a one-pot procedure. Moreover, a wide scope of substrates could effectively participate in the process affording the target products in moderate to excellent yields. Copyright
- Zhang, Zhanyi,Zheng, Jia,Du, Qingwei,Zhang, Wei,Li, Yiqun
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experimental part
p. 1543 - 1547
(2012/09/07)
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- Aerobic ligand-free Suzuki coupling catalyzed by in situ-generated palladium nanoparticles in water
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A simple and efficient procedure for Suzuki coupling of aryl bromides/iodides with aryl- and alkylboronic acids catalyzed by in situ-generated palladium(0) nanoparticles in water without any ligand in open air to produce a variety of functionalized biaryls and alkyl-aryls has been developed. The boronic acids act here as the reducing agent for the formation of Pd nanoparticles. The reactions are remarkably fast (5 min) and high yielding. The catalyst is recyclable up to three runs without loss of efficiency.
- Saha, Debasree,Chattopadhyay, Kalicharan,Ranu, Brindaban C.
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scheme or table
p. 1003 - 1006
(2009/05/11)
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- Highly efficient copper(0)-catalyzed Suzuki-Miyaura cross-coupling reactions in reusable PEG-400
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Readily available copper powder with K2CO3 as the base was extremely effective catalyst for Suzuki-Miyaura coupling reaction performed in PEG-400, which afforded almost quantitative coupling products of aryl iodides. Using iodine as additive, coupling products of aryl bromides or chlorides could be obtained with moderate to good yields.
- Mao, Jincheng,Guo, Jun,Fang, Fubing,Ji, Shun-Jun
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p. 3905 - 3911
(2008/09/20)
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- The synthesis and applications of a micro-pine-structured nanocatalyst
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Dendritic nanoferrites with a micro-pine morphology have been synthesized for the first time under microwave irradiation conditions without using any reducing or capping reagent; the nanoferrites were then functionalized and coated with Pd metal, which catalyzes various organic transformations. The Royal Society of Chemistry 2008.
- Polshettiwar, Vivek,Nadagouda, Mallikarjuna N.,Varma, Rajender S.
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supporting information; experimental part
p. 6318 - 6320
(2009/04/13)
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- Pd-N-heterocyclic carbene (NHC) organic silica: synthesis and application in carbon-carbon coupling reactions
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The first Pd-N-heterocyclic carbene (NHC) complex in the form of organic silica was prepared using sol-gel method and its application in Heck and Suzuki reactions was demonstrated. These C-C coupling reactions proceeded efficiently under the influence of microwave irradiation, with excellent yield, without any change in catalytic activity for at least five reaction cycles, with negligible Pd concentration in the end product.
- Polshettiwar, Vivek,Varma, Rajender S.
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p. 4637 - 4643
(2008/09/20)
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- SEMI-SYNTHETIC GLYCOPEPTIDES WITH ANTIBACTERIAL ACTIVITY
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Semi- synthetic glycopeptides having antibacterial activity are described, in particular, the semi-synthetic glycopeptides described hereins are made by subjecting the a glycopeptide (Compound A, Compound B, COMPOUND H or Compound C) in acidic medium to hydrolyze the disaccharide moiety of the amino acid-4 of the parent glycopeptide to give the amino acid-4 monosaccharide; temporary protection of the amino grouρ(s); conversion of the monosaccharide to the amino-sugar derivative; acylation of the amino substituent on the amino acid-4 amino-substituted sugar moiety on these scaffolds with certain acyl groups; conversion of the acid moiety on the macrocyclic ring of these scaffolds to certain substituted amides and removal of the tempory aimo protection grouρ(s). Also provided are methods for the synthesis of the compounds, pharmaceutical compositions containing the compounds, and methods of use of the compounds for the treatment and/or prophylaxis of diseases, especially bacterial infections.
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Page/Page column 69
(2009/01/20)
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- One-pot preparation of unsymmetrical biaryls via Suzuki cross-coupling reaction of aryl halide using phase-transfer catalyst in a biphasic solvent system
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A one-pot synthetic method of unsymmetrical biaryls was developed via the Suzuki cross-coupling reaction of aryl halide using a phase-transfer catalyst in a biphasic solvent system. Copyright Taylor & Francis Group, LLC.
- Miura, Masanori,Koike, Takanori,Ishihara, Tsukasa,Sakamoto, Shuichi,Okada, Minoru,Ohta, Mitsuaki,Tsukamoto, Shin-Ichi
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p. 667 - 674
(2007/10/03)
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- Bis(2-diphenylphosphinoxynaphthalen-1-yl)methane: Transition metal chemistry, Suzuki cross-coupling reactions and homogeneous hydrogenation of olefins
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Transition metal complexes of bis(2-diphenylphosphinoxynaphthalen-1-yl) methane (1) are described. Bis(phosphinite) 1 reacts with Group 6 metal carbonyls, [Rh(CO)2Cl]2, anhydrous NiCl2, [Pd(C3H5)Cl]2/AgBF4 and Pt(COD)I2 to give the corresponding 10-membered chelate complexes 2, 3 and 5-8. Reaction of 1 with [Rh(COD)Cl]2 in the presence of AgBF4 affords a cationic complex, [Rh(COD){Ph2P(-OC 10H6)(μ-CH2)(C10H 6O-)PPh2-KP,KP}]BF4 (4). Treatment of 1 with AuCl(SMe2) gives mononuclear chelate complex, [(AuCl){Ph 2P(-OC10H6)(μ-CH2)(C 10H6O-)PPh2-KP,KP}] (9) as well as a binuclear complex, [Au(Cl){μ-Ph2P(-OC10H6)(μ- CH2)(C10H6O-)PPh2-KP,KP}AuCl] (10) with ligand 1 exhibiting both chelating and bridged bidentate modes of coordination respectively. The molecular structures of 2, 6, 7, 9 and 10 are determined by X-ray studies. The mixture of Pd(OAc)2 and 1 effectively catalyzes Suzuki cross-coupling reactions of a range of aryl halides with aryl boronic acid in MeOH at room temperature or at 60°C, giving generally high yields even under low catalytic loads. The cationic rhodium(I) complex, [Rh(COD){Ph2P(-OC10H6)(μ-CH 2)(C10H6O-)PPh2-KP,KP}]BF 4 (4) catalyzes the hydrogenation of styrenes to afford the corresponding alkyl benzenes in THF at room temperature or at 70°C with excellent turnover frequencies. The Royal Society of Chemistry 2006.
- Punji, Benudhar,Mague, Joel T.,Balakrishna, Maravanji S.
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p. 1322 - 1330
(2007/10/03)
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- Pyrimidinone compounds
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Pyrimidinone compounds of formula (I) are inhibitors of the enzyme Lp-PLA2 and of use in therapy, in particular for treating atherosclerosis.
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Page/Page column 8
(2008/06/13)
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- Catalyst for aromatic C—O, C—N, and C—C bond formation
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The present invention is directed to a transition metal catalyst, comprising a Group 8 metal and a ligand having the structure wherein R, R′ and R″ are organic groups having 1-15 carbon atoms, n=1-5, and m=0-4. The present invention is also directed to a method of forming a compound having an aromatic or vinylic carbon-oxygen, carbon-nitrogen, or carbon-carbon bond using the above catalyst. The catalyst and the method of using the catalyst are advantageous in preparation of compounds under mild conditions of approximately room temperature and pressure.
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- Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bond-forming cross-couplings
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Pentaphenylferrocenyl di-tert-butylphosphine has been prepared in high yield from a two-step synthetic procedure, and the scope of various cross-coupling processes catalyzed by complexes bearing this ligand has been investigated. This ligand creates a remarkably general palladium catalyst for aryl halide amination and for Suzuki coupling. Turnovers of roughly 1000 were observed for aminations with unactivated aryl bromides or chlorides. In addition, complexes of this ligand catalyzed the formation of selected aryl ethers under mild conditions. The reactions encompassed electron-rich and electron-poor aryl bromides and chlorides. In the presence of catalysts containing this ligand, these aryl halides coupled with acyclic or cyclic secondary alkyl- and arylamines, with primary alkyl- and arylamines, and with aryl- and primary alkylboronic acids. These last couplings provide the first general procedure for reaction of terminal alkylboronic acids with aryl halides without toxic or expensive bases. The ligand not only generates highly active palladium catalysts, but it is air stable in solution and in the solid state. Palladium(0) complexes of this ligand are also air stable as a solid and react only slowly with oxygen in solution.
- Kataoka, Noriyasu,Shelby, Quinetta,Stambuli, James P.,Hartwig, John F.
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p. 5553 - 5566
(2007/10/03)
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- Purification of carboxaldehyde
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The invention is directed to the process of purifying 4′-chloro-4-biphenylcarboxaldehyde.
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- Palladium-catalyzed cross-coupling reaction of aryltriethoxysilanes with aryl bromides under basic aqueous conditions
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Aryltriethoxysilanes were cross-coupled with aryl bromides in high yield in the presence of a palladium catalyst and aqueous sodium hydroxide.
- Murata,Shimazaki,Watanabe,Masuda
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p. 2231 - 2233
(2007/10/03)
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- Inhibitors of acyl-CoA:cholesterol O-acetyltransferase (ACAT). Part 1: Identification and structure-activity relationships of a novel series of substituted N-alkyl-N-biphenylmethyl-N'-arylureas
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A series of N-alkyl-N-biphenylylmethyl-N'-arylurea and related derivatives represented by 1 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Linking of two phenyl groups via oxygen and introduction of fluorine at appropriate positions on the biphenyl moiety improved in vitro and in vivo activity. From this series of analogs, compound 40 (FR179254), which had potent in vitro potency (rabbit intestinal microsomes IC50 = 25 nM), showed excellent plasma cholesterol-lowering activity when administered via the diet (ED50 = 0.045 mg/kg). However, the hypocholesterolemic effect of this compound was moderate when dosed by oral gavage in PEG400 as a vehicle (ED50 = 5.3 mg/kg). Modification of the N'-aryl moiety led to the identification of compound 50 (FR182980) which was efficacious in both dosing models (ED50 = 0.034 mg/kg and 0.11 mg/kg, respectively).
- Tanaka, Akira,Terasawa, Takeshi,Hagihara, Hiroyuki,Sakuma, Yuri,Ishibe, Noriko,Sawada, Masae,Takasugi, Hisashi,Tanaka, Hirokazu
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- One pot biaryl synthesis via in situ boronate formation
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The palladium-catalyzed cross-coupling reaction of aryl halides or aryl triflates with diborane 1 yielded structurally diverse aryl boronates which were reacted in situ with aryl halides or aryl triflates to afford a variety of biaryls in moderate to high yield.
- Giroux, Andre,Han, Yongxin,Prasit, Petpiboon
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p. 3841 - 3844
(2007/10/03)
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- Halophenyl substituted dioxanes
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Compounds of the formula STR1 wherein A1 denotes a single covalent bond and A2 denotes 1,4-phenylene or trans-1,4-cyclohexylene or A1 denotes trans-1,4-cyclohexylene and A2 denotes a single covalent bond; X
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- Synthesis of Water Soluble 8-Substituted 5-Deazaflavins
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By oxidative cyclization of 5,5'-arylmethylenebis(6-methylaminouracil) derivatives with diethyl azodicarboxylate a number of 5-deazaisoalloxazines were synthesized having at the C(8) position a substituent that causes a bathochromic shift varying between 20 and 130 nm, depending on the substituent.To increase the solubility in aqueous media 8-substituted 5-deazaflavins were prepared having a carboxymethyl group at the N(3) position.The carboxymethyl group was introduced prior to the oxidative cyclization.
- Link, P. A. J.,Plas, H. C. van der,Mueller, F.
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p. 873 - 878
(2007/10/02)
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- Dioxolane derivatives
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The invention is concerned with novel dioxolane derivatives of the formula: STR1 in which Ra is hydrogen or (1-4C)alkyl and Rb is (1-4C)alkyl or phenyl optionally bearing a halogeno substituent; their production; and their use for the manufacture of certain known anti-arthritic acids of the formula: STR2 and, in particular, those acids in which Ra =Rb =methyl or Ra =ethyl and Rb =phenyl, by a novel reduction process. The preferred reduction procedures involve the use of an alkali metal borohydride or cyanoborohydride in the presence of a noble metal catalyst, or the use of an α-branched alkyl or cycloalkyl Grignard agent. The use of the derivatives of formula I avoids the need for potentially toxic reagents and reactive intermediates in the previously known processes for the production of the acids of formula V.
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- Monobenzoxazolylstilbenes
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Monobenzoxazolylstilbenes of formula STR1 wherein R--O is lower alkoxy and stands in one of the positions 5 or 6, R1 is hydrogen or lower alkyl and R2 is hydrogen, chlorine or lower alkyl.
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- Palladium nanoparticles encapsulated in MIL-101-NH2 catalyzed one-pot reaction of Suzuki-Knoevenagel reaction
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Bifunctional Cr-MOF catalysts containing palladium nanoparticles (NPs) have been prepared. Combining the high activity of Pd NPs and base sites in MIL-101-NH2, the catalysts (Pd?MIL-101-NH2) exhibited distinct catalytic activity in a
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