- Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls
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Heteroaromatic biaryls are core scaffolds found in a plethora of pharmaceuticals; however, their direct synthesis by the Suzuki cross-coupling is limited to heteroaromatic halide starting materials. Here, we report a direct synthesis of diverse nitrogen-containing heteroaromatic biaryls by Pd-catalyzed decarbonylative Suzuki cross-coupling of widely available heterocyclic carboxylic acids with arylboronic acids. The practical and modular nature of this cross-coupling enabled the straightforward preparation of >45 heterobiaryl products using pyridines, pyrimidines, pyrazines, and quinolines in excellent yields. We anticipate that the modular nature of this protocol will find broad application in medicinal chemistry and drug discovery research.
- Blakemore, David C.,Cervantes-Reyes, Alejandro,Chinigo, Gary M.,Smith, Aaron C.,Szostak, Michal
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supporting information
p. 1678 - 1683
(2022/03/14)
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- QUATERNARY LACTAM COMPOUND AND PHARMACEUTICAL USE THEREOF
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A quaternary lactam compound of formula (I). The compound is used in the manufacture of a medicament for the treatment and/or prevention of thrombotic or thromboembolic disorders.
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Paragraph 0264-0266; 0273-0274
(2021/02/05)
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- Ferrocenyl palladacycles derived from unsymmetrical pincer-type ligands: Evidence of Pd(0) nanoparticle generation during the Suzuki-Miyaura reaction and applications in the direct arylation of thiazoles and isoxazoles
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A new family of ferrocenyl-palladacycle complexes Pd(L1)Cl (Pd1) and Pd(L2)Cl (Pd2) were synthesized and characterized by UV-visible, IR, ESI-MS, and NMR spectral studies. The molecular structures of Pd1 and Pd2 were determined by X-ray crystallographic studies. Palladacycle catalyzed Suzuki-Miyaura cross-coupling reactions were investigated utilizing the derivatives of phenylboronic acids and substituted chlorobenzenes. Mechanistic investigation authenticated the generation of Pd(0) nanoparticles during the catalytic cycle and the nanoparticles were characterized by XPS, SEM and TEM analysis. Direct C-H arylation of thiazole and isoxazole derivatives employing these ferrocenyl-palladacycle complexes was examined. The reaction model for the arylation reaction implicating the in situ generation of Pd(0) nanoparticles was proposed.
- Maji, Ankur,Singh, Anshu,Mohanty, Aurobinda,Maji, Pradip K.,Ghosh, Kaushik
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supporting information
p. 17083 - 17096
(2019/11/26)
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- NOVEL CHIRAL DIHYDROBENZOOXAPHOSPHOLE LIGANDS AND SYNTHESIS THEREOF
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This invention relates to novel phosphorous ligands useful for organic transformations. Methods of making and using the ligands in organic synthesis are described. The invention also relates to processes for preparing the novel ligands.
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Paragraph 0298
(2018/06/15)
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- [2,2′-bipyridin]-6(1 H)-one, a Truly Cooperating Ligand in the Palladium-Mediated C-H Activation Step: Experimental Evidence in the Direct C-3 Arylation of Pyridine
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The ligand [2,2′-bipyridin]-6(1H)-one (bipy-6-OH) has a strong accelerating effect on the Pd-catalyzed direct arylation of pyridine or arenes. The isolation of relevant intermediates and the study of their decomposition unequivocally show that the deprotonated coordinated ligand acts as a base and assists the cleavage of the C-H bond. Mechanistic work indicates that the direct arylation of pyridine with this ligand occurs through a Pd(0)/Pd(II) cycle. Because of this dual ligand-intramolecular base role, there is no need for an available coordination site on the metal for an external base, a difficulty encountered when chelating ligands are used in coupling reactions that involve a C-H cleavage step.
- Salamanca, Vanesa,Toledo, Alberto,Albéniz, Ana C.
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supporting information
p. 17851 - 17856
(2019/01/04)
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- Synthesis of Bi(hetero)aryls via Sequential Oxidation and Decarboxylation of Benzylamines in a Batch/Fully Automated Continuous Flow Process
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Catalytic dehydrogenative cross-coupling of two C–H bonds represents a green strategy in view of the atom- and step-economy. However, the challenge is to discover a new innovative bond strategy, especially for the direct coupling between Csp2–H
- Mahajan, Bhushan,Aand, Dnyaneshwar,Singh, Ajay K.
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supporting information
p. 2831 - 2835
(2018/06/21)
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- Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water
-
N-(3-Chloro-2-quinoxalinyl)-N′-arylimidazolium salts (aryl = 2,6-diisopropylphenyl [HL1Cl]Cl, aryl = mesityl [HL2Cl]Cl) have been synthesized by treating 2,3-dichloroquinoxaline with the corresponding N′-arylimidazole in neat water. Facile reactions of these imidazolium salts with Pd(PPh3)4 and Pd2(dba)3/PPh3 (dba = dibenzyledene acetone) at 50 °C have afforded zwitterionic palladium(ii) complexes [Pd(HL1)(PPh3)Cl2] (I) and [Pd(HL2)(PPh3)Cl2] (II) in excellent yields. I and II have been tested for their ability to catalyze Suzuki-Miyaura cross coupling (SMC) reactions in neat water/K2CO3 and are found to be highly active for carrying out these reactions between aryl bromides and organoboron reagents. Furthermore, the scope of the catalyst I was also examined by employing (hetero)aryl bromides, hydrophilic aryl bromides, benzyl bromides and various organoboron reagents. More than 80 aryl/benzyl bromide-arylboronic acid combinations were screened in neat water/K2CO3 and it was found that I was a versatile catalyst, which produced biaryls/diarylmethanes in excellent yields. A TON of 82 000 was achieved by using I. Studies on the mechanism have also been carried out to investigate the involvement of carbene complexes in the catalytic path. Poison tests and a two-phase test were also conducted and the results are reported.
- Ramakrishna,Dastagiri Reddy
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p. 8598 - 8610
(2017/07/12)
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- ONE STEP DIRECT ARYLATION OF COMMODITY CHEMICALS TO SPECIALTY CHEMICALS BY TANDEM CATALYTIC PLATFORM
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The present invention relates to a continuous direct arylation process based on a tandem catalyst for synthesizing specialty chemicals. A method for synthesizing an aryl-aryl structure from a substrate selected from the group consisting of benzyl alcohol, benzyl amine and toluene which are low value added compounds is developed using a silver ion-containing tandem catalyst. The method is applied for synthesizing hexaphenyl arylene and can be applied for synthesizing high value added compounds (not only natural substances and chemical compounds but pharmaceutical and agricultural pesticide relative fields) directly from primary raw materials through the reaction.COPYRIGHT KIPO 2017
- -
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Paragraph 0044-0048; 0106
(2018/02/28)
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- DFT Studies Provide Mechanistic Insight into Nickel-Catalyzed Cross-Coupling Involving Organoaluminum-Mediated C-O Bond Cleavage
-
Density functional theory (DFT) calculations were performed to examine the reaction pathway of Ni-catalyzed cross-coupling with organoaluminum through C-O bond cleavage. The results indicate that the strong Lewis acidity of organoaluminums significantly f
- Yang, Ze-Kun,Wang, Chao,Uchiyama, Masanobu
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p. 2565 - 2568
(2017/11/28)
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- Revisitation of Organoaluminum Reagents Affords a Versatile Protocol for C-X (X = N, O, F) Bond-Cleavage Cross-Coupling: A Systematic Study
-
A revisit of organoaluminum reagents for cross-coupling reactions has opened up several types of C-C bond formation protocols through cleavage of phenolic/alcoholic C-O and C-F and ammonium C-N bonds. Catalyzed by the commercially available NiCl2(PCy3)2 catalyst, these reactions proceed smoothly with a wide range of substrates and broad functional group compatibility, providing a versatile methodology for organoaluminum-mediated cross-coupling processes.
- Ogawa, Hiroyuki,Yang, Ze-Kun,Minami, Hiroki,Kojima, Kumiko,Saito, Tatsuo,Wang, Chao,Uchiyama, Masanobu
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p. 3988 - 3994
(2017/06/19)
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- Manganese-Catalyzed Aerobic Heterocoupling of Aryl Grignard Reagents
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An improved protocol has been developed for the MnCl2-catalyzed cross-coupling reaction of two arylmagnesium bromides under dioxygen. The reaction was achieved by using the Grignard reagents in a 2:1 ratio and 20 % of MnCl2. Very good yields of the heterocoupling product were obtained when the limiting Grignard reagent underwent little homocoupling under the reaction conditions. Arylmagnesium bromides that contain p-methoxy, p-(dimethylamino), p-fluoro, and p-chloro substituents were shown to afford high product yields in the cross-coupling reactions with a variety of substituted aryl Grignard reagents. Heterocyclic Grignard reagents, on the other hand, were less effective substrates for this transformation because of the rapid homocoupling of these reagents under the reaction conditions.
- Ghaleshahi, Hajar Golshahi,Antonacci, Giuseppe,Madsen, Robert
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p. 1331 - 1336
(2017/03/23)
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- An active catalytic system for Suzuki-Miyaura cross-coupling reactions using low levels of palladium loading
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An easily available Pd(OAc)2/(2-(anthracen-9-yl)-1H-inden-3-yl) dicyclohexylphosphine/toluene/iPrOH/water catalytic system was developed, which shows high catalytic activity in the Suzuki-Miyaura cross-coupling reactions of a diverse array of aryl and heteroaryl chlorides with Pd loadings down to 0.01 mol%.
- Yan, Meng-Qi,Yuan, Jia,Lan, Fang,Zeng, Si-Hao,Gao, Meng-Yue,Liu, Sheng-Hua,Chen, Jian,Yu, Guang-Ao
-
supporting information
p. 3924 - 3929
(2017/07/10)
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- In situ generated and stabilized Pd nanoparticles by N2,N4,N6-tridodecyl-1,3,5-triazine-2,4,6-triamine (TDTAT) as a reactive and efficient catalyst for the Suzuki-Miyaura reaction in water
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In situ generated Pd nanoparticles in the presence of N2,N4,N6-tridodecyl-1,3,5-triazine-2,4,6-triamine (TDTAT) were found to be an efficient catalyst for the Suzuki-Miyaura coupling reaction in water. It seems that TDTAT not only acts as a ligand for stabilization of the produced nanoparticles, but also as a surfactant to facilate the reaction in water, and reduces Pd(ii) to Pd(0). The TEM analysis of the reaction mixture showed that Pd nanoparticles with an average size of ~5 nm are produced, which act as an efficient catalyst in the Suzuki-Miyaura coupling reaction.
- Iranpoor, Nasser,Rahimi, Sajjad,Panahi, Farhad
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p. 3084 - 3090
(2016/01/16)
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- Carboxyamido/carbene ligated palladium (II) complex: A versatile catalyst for the synthesis of aryl-substituted heteroarenes
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Carboxy amido/carbene ligated Pd-complex catalyzed Suzuki-Miyaura cross-coupling of aryl-boronic acids with heteroaryl bromides is described. The protocol has a broad substrate scope that includes electron-rich, electron-deficient and sterically hindered arylboronic acids and heteroaryl bromides. The catalytic activity of the catalyst has been further investigated in the coupling of 2,6-dibromopyridine with arylboronic acids.
- Vishnuvardhan Reddy, Police,Parsharamulu, Thupakula,Annapurna, Manne,Likhar, Pravin R.,Kantam, Mannepalli Lakshmi,Bhargava, Suresh
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supporting information
p. 150 - 153
(2016/12/06)
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- Synthesis of 3-Arylpyridines via Palladium/Copper-Catalyzed Annulation of Allylamine/1,3-Propanediamine and Aldehydes
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A novel and efficient method for the synthesis of 3-arylpyridines from allylamine/propanediamine and aldehydes by palladium/copper-catalyzed oxidative tandem cyclization has been developed. With this reaction, a series of desired 3-arylpyridines was synthesized in moderate yields via C-C/C-N bond formation and 6-endo/exo-trig cyclization.
- Yang, Xiaodong,Yang, Shenghua,Xiang, Likui,Pang, Xiaobo,Chen, Baohua,Huang, Guosheng,Yan, Rulong
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p. 3732 - 3736
(2016/01/25)
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- Nickel-Catalyzed Decarbonylative Coupling of Aryl Esters and Arylboronic Acids
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A variety of functionalized biaryls can be accessed by coupling aryl and heteroaryl esters with boronic acids in Suzuki-Miyaura-type decarbonylative cross-coupling catalyzed by an affordable catalyst system composed of Ni(cod)2 and PCy3. The methodology is tolerant of a variety of functional groups and presents an attractive alternative to the use of palladium catalysis currently used in industry to acquire such bis(hetero)aryls, but also reveals challenges associated with nickel catalysis of esters in cross-coupling chemistry.
- Laberge, Nicole A.,Love, Jennifer A.
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p. 5546 - 5553
(2015/09/01)
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- P2Et Phosphazene: A Mild, Functional Group Tolerant Base for Soluble, Room Temperature Pd-Catalyzed C-N, C-O, and C-C Cross-Coupling Reactions
-
The non-nucleophilic organic superbase P2Et phosphazene can enable a broad range of palladium-catalyzed cross-coupling reactions, including C-C, C-N, and C-O couplings of aryl chlorides, bromides, and iodides at room temperature. The mildness a
- Buitrago Santanilla, Alexander,Christensen, Melodie,Campeau, Louis-Charles,Davies, Ian W.,Dreher, Spencer D.
-
supporting information
p. 3370 - 3373
(2015/07/15)
-
- Cross-coupling study of iodo/chloropyridines and 2-chloroquinoline with atom-economic triarylbismuth reagents under Pd-catalysis
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This study describes the palladium-catalyzed couplings of iodopyridines, chloropyridines, and chloroquinoline with atom-economic BiAr3 reagents in sub-stoichiometric loadings. Mono-arylations of iodo and chloropyridines produced arylpyridines i
- Rao, Maddali L.N.,Dhanorkar, Ritesh J.
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p. 338 - 349
(2015/03/04)
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- Triarylbismuthanes as threefold aryl-transfer reagents in regioselective cross-coupling reactions with bromopyridines and quinolines
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Cross-coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd-catalysed conditions are disclosed. The reactivity was high with both mono- and dibromopyridyl substrates, and mono- and bis-couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one-pot strategy provided a simple and straightforward synthesis of both symmetrical and unsymmetrical diarylpyridines. Arylations of 2-bromo- and 3-bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd-catalysed conditions. Copyright
- Rao, Maddali L.N.,Dhanorkar, Ritesh J.
-
supporting information
p. 5214 - 5228
(2014/10/15)
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- Palladium nanoparticles supported on agarose-functionalized magnetic nanoparticles of Fe3O4 as a recyclable catalyst for C-C bond formation via Suzuki-Miyaura, Heck-Mizoroki and Sonogashira-Hagihara coupling reactions
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In this paper, the preparation of palladium nanoparticles supported on agarose-functionalized magnetic nanoparticles of Fe3O4 is described. The new material was characterized by EDX, TEM, TGA, FT-IR, VSM, AAS, and solid UV-visible analysis. This magnetic material has been successfully applied as a highly efficient, magnetically recoverable and air-stable catalyst for the Suzuki-Miyaura, Heck-Mizoroki and Sonogashira-Hagihara coupling reactions. Using this material as a catalyst, a wide range of substrates was employed for carbon-carbon bond formation in wet PEG 200.
- Firouzabadi, Habib,Iranpoor, Nasser,Gholinejad, Mohammad,Akbari, Samira,Jeddi, Neda
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p. 17060 - 17070
(2014/05/06)
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- Direct arylation of pyridines without the use of a transition metal catalyst
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A method for achieving the direct arylation of pyridines with phenylhydrazine hydrochloride was developed in this study. This new reaction proceeds readily at room temperature without the use of any transition metal catalysts. This method allows rapid access to various arylated heterocycles that are more difficult to access through traditional methods.
- Li, Yahui,Liu, Wei,Kuang, Chunxiang
-
supporting information
p. 7124 - 7127
(2014/07/07)
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- Pd-catalyzed C3-selective arylation of pyridines with phenyl tosylates
-
We have discovered that phenyl tosylates can be used to arylate pyridines at the C3-position using a Pd(OAc)2-1,10-phenanthroline catalyst system. We also discovered that the reaction of 4-methylpyridine with naphthyl tosylates occurred on the methyl group instead of at the C3-position. The Royal Society of Chemistry 2013.
- Dai, Fenglin,Gui, Qingwen,Liu, Jidan,Yang, Zhiyong,Chen, Xiang,Guo, Ruqing,Tan, Ze
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supporting information
p. 4634 - 4636
(2013/06/05)
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- Ether-imidazolium carbenes for Suzuki-Miyaura cross-coupling of heteroaryl chlorides with Aryl/heteroarylboron reagents
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Easily accessible and handled ether-imidazolium chlorides were developed as ligand precursors. The coupling reactions of heteroaryl chlorides with aryl/heteroarylboronic acids and esters were catalyzed by the palladium/ether-imidazolium chloride system with high substrate tolerance to give various heterobiaryls in good to excellent yields.
- Kuriyama, Masami,Matsuo, Seira,Shinozawa, Mina,Onomura, Osamu
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supporting information
p. 2716 - 2719
(2013/07/19)
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- Metal-free arylation of benzene and pyridine promoted by amino-linked nitrogen heterocyclic carbenes
-
An amino-linked nitrogen heterocyclic carbene (amino-NHC), 1-tBu, has been shown to mediate carbon-carbon coupling through the direct C-H functionalization of benzene and pyridine in the absence of a metal catalyst. Using EPR, the first spectroscopic evidence corroborating the single electron transfer mechanism for the metal-free carbon-carbon coupling manifold, as reported by others, is introduced.
- Chen, Wen-Ching,Hsu, Yu-Chen,Shih, Wei-Chun,Lee, Ching-Yu,Chuang, Wen-Han,Tsai, Yi-Fang,Chen, Peter Ping-Yu,Ong, Tiow-Gan
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supporting information; experimental part
p. 6702 - 6704
(2012/07/14)
-
- De novo synthesis of 1,4-dihydropyridines and pyridines
-
An efficient and general method for the synthesis of 1,4-dihydropyridines and pyridines based on a lithiation/isomerization/intramolecular carbolithiation sequence is reported. This procedure provides an efficient, divergent, and straightforward entry to a wide range of polysubstituted dihydropyridines and pyridines starting from readily available N-allyl-ynamides.
- Gati, Wafa,Rammah, Mohamed M.,Rammah, Mohamed B.,Couty, Francois,Evano, Gwilherm
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p. 9078 - 9081
(2012/07/13)
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- Intramolecular carbolithiation of N-allyl-ynamides: An efficient entry to 1,4-dihydropyridines and pyridines - Application to a formal synthesis of sarizotan
-
We have developed a general synthesis of polysubstituted 1,4-dihydropyridines and pyridines based on a highly regioselective lithiation/6-endo-dig intramolecular carbolithiation from readily available N-allyl-ynamides. This reaction, which has been successfully applied to the formal synthesis of the anti-dyskinesia agent sarizotan, further extends the use of ynamides in organic synthesis and further demonstrates the synthetic efficiency of carbometallation reactions.
- Gati, Wafa,Rammah, Mohamed M.,Rammah, Mohamed B.,Evano, Gwilherm
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p. 2214 - 2222
(2013/02/23)
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- Aryl-aryl bond formation by the fluoride-free cross-coupling of aryldisiloxanes with aryl bromides
-
The prevalence of the biaryl structural motif in biologically interesting and synthetically important molecules has inspired considerable interest in the development of methods for aryl-aryl bond formation. Herein we describe a novel strategy for this process involving the fluoride-free, palladium-catalysed cross-coupling of readily accessible aryldisiloxanes and aryl bromides. Using a statistical-based optimisation process, preparatively useful reaction conditions were formulated to allow the cross-coupling of a wide range of different substrates. This methodology represents an attractive, cost-efficient, flexible and robust alternative to the traditional transition-metal-catalysed routes typically used to generate molecules containing the privileged biaryl scaffold.
- Boehner, Christine M.,Frye, Elizabeth C.,O'Connell, Kieron M. G.,Galloway, Warren R. J. D.,Sore, Hannah F.,Dominguez, Patricia Garcia,Norton, David,Hulcoop, David G.,Owen, Martin,Turner, Gillian,Crawford, Claire,Horsley, Helen,Spring, David R.
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p. 13230 - 13239
(2012/02/06)
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- Thermoregulated ligand-palladium-catalyzed Suzuki reaction in water
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An efficient and recyclable protocol for the Suzuki reaction in water has been developed based on the cloud point of thermoregulated ligand Ph 2P(CH2CH2O)nCH3 (n = 22). This method allows the preparation of a variety of biaryls in high yields and the catalytic system can be recycled four times with high efficiency.
- Liu, Ning,Liu, Chun,Yan, Bo,Jin, Zilin
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experimental part
p. 168 - 172
(2012/04/04)
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- Green synthesis of fluorinated biaryl derivatives via thermoregulated ligand/palladium-catalyzed Suzuki reaction
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Fluorinated compounds have attracted considerable attention in pharmaceuticals, agrochemicals and material science due to their unique physical properties. This paper reports an efficient and environmentally benign protocol for the Suzuki reaction of aryl halides with fluorinated arylboronic acids over a thermoregulated ligand/palladium catalyst using water as sole medium, affording a variety of fluorinated biaryls, including fluorinated liquid crystals, in excellent yields. The catalyst could be recycled four times with high activity. The active catalyst was proved to be a palladium/ligand complex via a mercury-poisoning test.
- Liu, Ning,Liu, Chun,Jin, Zilin
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supporting information; experimental part
p. 2641 - 2647
(2011/07/09)
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- Ligand-promoted C3-selective arylation of pyridines with Pd catalysts: Gram-scale synthesis of (±)-preclamol
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The first example of Pd-catalyzed, C3-selective arylation of unprotected pyridines has been developed by employing a catalytic system consisting of Pd(OAc)2 and 1,10-phenanthroline. This protocol provides an expeditious route to an important class of 3-arylpyridines and 3-arylpiperidines frequently found in bioactive compounds. A brief synthesis of the drug molecule (±)-preclamol is also reported.
- Ye, Mengchun,Gao, Guo-Lin,Edmunds, Andrew J. F.,Worthington,Morris, James A.,Yu, Jin-Quan
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supporting information; experimental part
p. 19090 - 19093
(2012/01/07)
-
- Ionic liquid supported organotin reagents: Green tools for stille cross-coupling reactions with brominated substrates
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Efficiency of ionic liquid supported organotin reagents in Stille cross-coupling reactions involving aryl bromides has been investigated. In a general manner, products were isolated with good yields by using a very simple catalytic system without the need of solvent, ligand, or additives. The organotin compounds were recycled without loss of activity and the contamination by tin was limited and controlled ([Sn] 3 ppm). Clean tin's good! Efficiency of ionic liquid supported organotin reagents in Stille cross-coupling reactions involving aryl bromides has been investigated. Products were isolated with good yields by using a verysimple catalytic system. Organotin compounds were recycled without loss of activity and the contamination by tin was limited ([Sn] 3 ppm).
- Louaisil, Nicolas,Pham, Phuoc Dien,Boeda, Fabien,Faye, Djibril,Castanet, Anne-Sophie,Legoupy, Stephanie
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supporting information; experimental part
p. 143 - 149
(2011/03/18)
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- A general and highly efficient method for the construction of aryl-substituted N-heteroarenes
-
A general, simple and highly efficient method has been developed for the Pd(OAc)2-catalyzed ligand-free and aerobic Suzuki reaction of N-heteroaryl halides, which is strongly dependent on the molecular structure of solvent. A general, simple and highly efficient method has been developed for the Pd(OAc)2-catalyzed ligand-free and aerobic Suzuki reaction of N-heteroaryl halides including 2-pyridyl bromides, 3-pyridyl bromides, 3-quinolyl bromides, 5-pyrimidyl bromides and 2-pyrazyl chloride, which is strongly dependent on the molecular structure of solvent.
- Liu, Chun,Han, Na,Song, Xiaoxiao,Qiu, Jieshan
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supporting information; experimental part
p. 5548 - 5551
(2011/02/19)
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- Bis(imino)pyridine palladium(II) complexes: Synthesis, structure and catalytic activity
-
Bis(imino)pyridine palladium(II) complexes 3-6 were synthesized by two different methods. The structure of complexes 3 and 4 has been confirmed by X-ray structure analysis. The catalytic studies show that bis(imino)pyridine palladium(II) complexes are highly efficient catalysts in the Suzuki-Miyaura reaction and the complex 4 was used to catalyze the synthesis of fluorinated liquid crystalline compounds via Suzuki coupling reaction. Crown Copyright
- Liu, Ping,Zhou, Li,Li, Xiaogang,He, Ren
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experimental part
p. 2290 - 2294
(2009/10/23)
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- A Pd(II)-catalyzed ring-expansion reaction of cyclic 2-azidoalcohol derivatives: Synthesis of azaheterocycles
-
(Chemical Equation Presented) A Pd(II)-catalyzed ring expansion-reaction of cyclic 2-azidoalcohol derivatives was found to proceed via an unprecedented C-C bond cleavage-C-N bond formation sequence, providing substituted azaheterocycles.
- Chiba, Shunsuke,Xu, Yan-Jun,Wang, Yi-Feng
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supporting information; experimental part
p. 12886 - 12887
(2009/12/06)
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- Palladium/tetraphosphine catalyzed suzuki cross-coupling of heteroarylboronic acids with aryl halides
-
(Chemical Equation Presented) cis,cis,cis-1,2,3,4- Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C3H 5)]2 efficiently catalyses the Suzuki reaction of heteroarylboronic acids with aryl bromides and also the coupling of arylboronic acids with heteroaryl bromides. The coupling of thiophene- or benzothiopheneboronic acids, furan- or benzofuranboronic acids and 3-pyridineboronic acid with a variety of aryl bromides gave the corresponding coupling products in good yields. However, in most cases, better results in terms of ratio substrate/catalyst were obtained for the reverse reaction using heteroaryl bromides with arylboronic acids.
- Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
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p. 109 - 118
(2008/09/18)
-
- NEW COMPOUNDS
-
The invention relates to new bicyclic heterocyclic derivative compounds, to pharmaceutical compositions comprising said compounds and to the use of said compounds in the treatment of diseases, e.g. cancer.
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-
Page/Page column 131-132
(2008/12/06)
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- Activity of nitrogen-containing and non-nitrogen-containing bisphosphonates on tumor cell lines
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We synthesized and tested three series of bisphosphonates for their activity in inhibiting the growth of three human tumor cell lines: MCF-7 (breast), NCI-H460 (lung), and SF-268 (CNS). The first series of compounds consisted of 49 nitrogen-containing bis
- Zhang, Yonghui,Leon, Annette,Song, Yongcheng,Studer, Danielle,Haase, Christa,Koscielski, Lukasz A.,Oldfield, Eric
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p. 5804 - 5814
(2007/10/03)
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- Suzuki coupling reactions of heteroarylboronic acids with aryl halides and arylboronic acids with heteroaryl bromides using a tetraphosphine/palladium catalyst
-
cix,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/ [PdCl(C3H5)]2 efficiently catalyses the Suzuki reaction of heteroarylboronic acids with aryl bromides and also the coupling of arylboronic acids with heteroaryl bromides. The coupling of thiopheneboronic acids, 3-furanboronic acid and 3-pyridineboronic acid with a variety of aryl bromides gave the corresponding adducts in good yields. However, in most cases, better results in terms of substrate/catalyst ratio were obtained for the reaction of heteroaryl bromides with arylboronic acids. Georg Thieme Verlag Stuttgart.
- Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
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p. 2057 - 2061
(2007/10/03)
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- METHOD FOR THE PRODUCTION OF 5-ARYL NICOTINALDEHYDES
-
The invention relates to a method for producing 5-aryl nicotinaldehydes by reducing the corresponding 5-aryl nicotinic acids by means of catalytic hydrogenation with a palladium complex that is stabilized with the aid of a phosphine in the presence of di-
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-
Page/Page column 5-6
(2008/06/13)
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- Efficient coupling of heteroaryl halides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst
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Cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane: ·1/2[PdCl(C3H5)]2 system catalyses the Suzuki cross-coupling of heteroaryl halides with a range of arylboronic acids with very high ratio substrate/catalyst in good yields. Substrates such as pyridines, quinolines, thiophenes, an indole, pyrimidines or a furane have been used successfully.
- Feuerstein, Marie,Doucet, Henri,Santelli, Maurice
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p. 327 - 336
(2007/10/03)
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- Efficient coupling of heteroaryl bromides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst
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The cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C 3H5)]2 system catalyses the Suzuki cross-coupling of heteroaryl bromides with arylboronic acids with a very high substrate/catalyst ratio in good yields. Substrates such as pyridines, quinolines, thiophenes, an indole, a pyrimidine or a furane have been used successfully.
- Feuerstein, Marie,Doucet, Henri,Santelli, Maurice
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p. 5659 - 5662
(2007/10/03)
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- Palladium-tetraphosphine catalysed cross coupling of aryl bromides with arylboronic acids: Remarkable influence of the nature of the ligand
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The cis, cis, cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane- [PdCl(C3H5)]2 system catalyses the cross coupling of aryl bromides with arylboronic acids with very high substrate-catalyst ratios in good yields; a turnover number of 28 000 000 can be obtained for the addition of 4-bromobenzophenone to benzeneboronic acid in the presence of this catalyst.
- Feuerstein,Laurenti,Bougeant,Doucet,Santelli
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p. 325 - 326
(2007/10/03)
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- Quantitative Determination of the Electronic Effects of Pyridyl Groups
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The series of ? constants of 2-, 3-, and 4-pyridyl groups was calculated on the basis of data from the 1H, 13C, and 19F NMR spectra of isomeric aminophenyl-, phenyl-, and fluorophenylpyridines.The literature ? constants and the values found in the research were analyzed.
- Shkurko, O. P.,Baram, S. G.,Mamaev, V. P.
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