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Microwave-assisted copper catalyzed coupling reaction of aryl halides with terminal alkynes
Coupling reaction of aryl halides with terminal alkynes using catalyst system of copper (I)-triphenylphosphine proceeds efficiently in the presence of potassium carbonate under microwave irradiation to give the corresponding unsymmetrical acetylenes in go
Wang, Jin-Xian,Liu, Zhanxiang,Hu, Yulai,Wei, Bangguo,Kang, Liqin
p. 1937 - 1945
(2002)
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A Co-Cu bimetallic magnetic nanocatalyst with synergistic and bifunctional performance for the base-free Suzuki, Sonogashira, and C-N cross-coupling reactions in water
A novel magnetically recyclable bimetallic catalyst was prepared by anchoring imidazolium moiety and PEG chains on Fe3O4 NPs and named as Fe3O4?PEG/Cu-Co. It was found to be a powerful catalyst for the Sonogashira, Suzuki, and C-N cross-coupling reactions in water as a green solvent without the need for any external base. Fe3O4?PEG/Cu-Co was well characterized with FT-IR, FE-SEM, TEM, VSM, EDX, ICP, UV-visible, CV, and XPS analyses. Optimum ranges of parameters such as time, temperature, and amount of catalyst were investigated by Design-Expert 10.0.7 software for C-C Suzuki, Sonogashira, and C-N cross-coupling reactions to find the optimum conditions. The catalyst was compatible with a variety of aryl halides and N-arenes and gave favorable coupling products with good to high yields for all of them. Hot filtration and Hg poisoning tests involving the nanocatalyst revealed the stability, low metal leaching, and heterogeneous nature of the catalyst. Reaction mechanisms were proposed by study of the UV-visible spectra in situ as well as hydroquinone tests during the progress of reactions. In situ XPS analysis was also used to study the reaction mechanism. To prove the synergistic performance of Co and Cu in the catalyst, its various homologues were synthesized and applied to a model reaction separately, and then their catalytic activities were investigated. Finally, the catalyst could be recovered from the reaction mixture simply, and reused for several cycles with a minimum loss in catalytic activity and performance.
Allahresani, Ali,Kazemnejadi, Milad,Nasseri, Mohammad Ali,Rezazadeh, Zinat
p. 10645 - 10660
(2020/09/18)

Hybrid hydrogels loaded with palladium nanoparticles – Catalysts for environmentally-friendly Sonogashira and Heck cross-coupling reactions
Palladium nanoparticles (PdNPs) were encapsulated within hybrid hydrogels made from an acylhydrazide-functionalised 1,3:2,4-dibenzylidene sorbitol (DBS-CONHNH2) low-molecular-weight gelator (LMWG) combined with agarose polymer gelator via in situ reduction of Pd(II). These heterogeneous gel-phase catalysts were successfully applied for copper-, amine- and phosphine-free Sonogashira cross-coupling reactions under environmentally-friendly conditions without the need for inert atmosphere reaction conditions. The PdNP-loaded gel was reused in Sonogashira couplings up to at least five times with no adverse effect on yield. The performance of solvated PdNP-loaded gel catalysts was compared with the dried xerogels. The xerogels can be used at higher temperatures, enhancing reaction kinetics albeit lowering reaction selectivity, but unlike the solvated gels, were unable to be easily recycled and reused. The PdNP-loaded gels also had good activity in Heck reactions, and although longer reaction times or higher temperatures were required than for the Sonogashira reaction, the reaction conditions were mild for a Heck coupling. In summary, we demonstrate a ‘waste-to-wealth’ methodology in which Pd(II) ‘waste’ is converted into a valuable gel-phase catalyst that can be used for green Sonogashira and Heck cross-coupling reactions.
Slavik, Petr,Smith, David K.
(2020/07/07)

The CuFe2O4@SiO2@ZrO2/SO42-/Cu nanoparticles: An efficient magnetically recyclable multifunctional Lewis/Br?nsted acid nanocatalyst for the ligand- and Pd-free Sonogashira cross-coupling reaction in water
Herein, the synthesis and application of copper-incorporated sulfated zirconium oxide supported on CuFe2O4 NPs (CuFe2O4@SiO2@ZrO2/SO42-/Cu NPs) as a novel Lewis/Br?nsted acid nanocatalyst were studied for the Sonogashira C-C cross-coupling reaction. The fabricated CuFe2O4@SiO2@ZrO2/SO42-/Cu catalyst exhibited efficient activity for a large variety of aryl iodides/bromides and, most importantly, aryl chlorides in water and in the presence of NaOH as a base in short reaction times. The catalyst was fully characterized by FTIR, TG-DTG, VSM, XRD, EDX, FE-SEM and TEM analyses. A synergetic effect could be considered to have arisen from the various Lewis acid and Br?nsted acid sites present in the catalyst. The efficient incorporation of copper into zirconia provided a robust highly stable hybrid, which prevented any metal leaching, whether from the magnetite moiety and/or Cu sites in the reaction mixture. Moreover, the catalyst was successfully recovered from the mixture by a simple external magnet and reused for at least 9 consecutive runs. Zero metal leaching, stability, consistency with a variety of substrates, fast performance, cost-effectiveness, environmental friendliness, and preparation with accessible and cheap materials are some of the advantages and highlights of the current protocol.
Nasseri, Mohammad Ali,Alavi, Seyyedeh Ameneh,Kazemnejadi, Milad,Allahresani, Ali
p. 20749 - 20759
(2019/07/12)

Magnetic Cu–Schiff base complex with an ionic tail as a recyclable bifunctional catalyst for base/Pd-free Sonogashira coupling reaction
Abstract: A Cu(II)–Schiff base complex containing imidazolium ionic phase was prepared and decorated on γ-Fe2O3 magnetic nanoparticles (γ-Fe2O3@Cu(II)IL-SB) and found to be an efficient catalyst for the Pd- and base-free Sonogashira coupling reaction. The heterogeneous catalyst was characterized by FTIR spectroscopy, UV–visible spectroscopy, FE-SEM, TEM, XRD spectroscopy, EDX spectroscopy, VSM, ICP spectroscopy, and atomic absorption spectroscopy. The coupling reactions were performed using the catalyst under mild and base-free conditions, and high-to-excellent yields were obtained for a variety of substrates. The catalyst demonstrates a dual-functionality arising from metal sites and imidazolium moieties and that the later plays a base role. Reusability and stability of γ-Fe2O3@Cu(II)IL-SB were studied several times, which can be reused up to eight consecutive runs with at least reduction in catalytic activity. Also, the mechanism of this bifunctional catalytic system was thoroughly investigated. Graphic abstract: A new and efficient method has been developed for the base- and Pd-free Sonogashira cross-coupling reactions of aryl halides with phenyl acetylene using a bifunctional γ-Fe2O3@Cu(II)IL-SB catalyst with imidazolium moiety under mild conditions[Figure not available: see fulltext.].
Nasseri, Mohammad Ali,Rezazadeh, Zinat,Kazemnejadi, Milad,Allahresani, Ali
p. 2693 - 2705
(2019/07/23)

Ligand-free, recyclable palladium-functionalized magnetite nanoparticles as a catalyst in the Suzuki-, Sonogashira, and Stille reaction
A magnetically reusable ligand-free Fe3O4 palladium functionalized catalyst system was successfully prepared without the use of reducing agents, but by making use of the reduction potential of magnetite. The stabilizer was variated depending on the investigated reaction, whereby poly(ethylene glycol) (PEG) stabilized nanoparticles were used for the Suzuki reaction, as it requires protic conditions, while oleic acid stabilized nanoparticles were used for the Sonogashira and Stille reaction. It was found that it was possible to perform the Suzuki reaction and the Sonogashira reaction resulting in good to excellent conversions under air. Despite the good results for the Suzuki and the Sonogashira reaction it was not possible to perform the Stille reaction using this easily synthesized catalyst system due to the poisoning of the reusable catalyst by the tin-compound. Furthermore, the reusable catalyst system was recycled and reused for five times, resulting in a separable, straightforward and less time-consuming catalyst system.
De Cattelle, Amaury,Billen, Arne,O'Rourke, Galahad,Brullot, Ward,Verbiest, Thierry,Koeckelberghs, Guy
(2019/11/13)

Discovery of a Potent Thiazolidine Free Fatty Acid Receptor 2 Agonist with Favorable Pharmacokinetic Properties
Free fatty acid receptor 2 (FFA2/GPR43) is a receptor for short-chain fatty acids reported to be involved in regulation of metabolism, appetite, fat accumulation, and inflammatory responses and is a potential target for treatment of various inflammatory and metabolic diseases. By bioisosteric replacement of the central pyrrolidine core of a previously disclosed FFA2 agonist with a synthetically more tractable thiazolidine, we were able to rapidly synthesize and screen analogues modified at both the 2- and 3-positions on the thiazolidine core. Herein, we report SAR exploration of thiazolidine FFA2 agonists and the identification of 31 (TUG-1375), a compound with significantly increased potency (7-fold in a cAMP assay) and reduced lipophilicity (50-fold reduced clogP) relative to the pyrrolidine lead structure. The compound has high solubility, high chemical, microsomal, and hepatocyte stability, and favorable pharmacokinetic properties and was confirmed to induce human neutrophil mobilization and to inhibit lipolysis in murine adipocytes.
Hansen, Anders H?jgaard,Sergeev, Eugenia,Bolognini, Daniele,Sprenger, Richard R.,Ekberg, Jeppe Hvidtfeldt,Ejsing, Christer S.,McKenzie, Christine J.,Rexen Ulven, Elisabeth,Milligan, Graeme,Ulven, Trond
supporting information
p. 9534 - 9550
(2018/10/24)

Heterogenized Cu (II) salen complex grafted on graphene oxide nanosheets as a precursing catalyst for the Pd-free Sonogashira coupling
Cu (II) salen complex immobilized on graphene oxide nanosheets [Cu (II) salen@GO] was synthesized with 3-chloropropyltrimethoxysilan as a linker and wholly characterized using various techniques like X-ray diffraction, Fourier-transform infrared, scanning electron microscopy/energy-dispersive X-ray spectroscopy, transmission electron microscopy, as well as atomic absorption spectroscopy (AAS). Cu (II) salen@GO as an effective heterogeneous catalyst has been investigated for the Sonogashira coupling reaction in dimethylsulfoxide with good to high yield (98%) in 4?hr at 110°C when the loading of Cu was 0.7?mmol?g?1 based on Cu element analysis by AAS. It was understood that heterogeneous catalyst was as active as its homogeneous analog, and presented good recoverability and no significant loss in activity within successive runs.
Ghabdian, Mahdieh,Nasseri, Mohammad A.,Allahresani, Ali,Motavallizadehkakhky, Alireza
(2018/09/25)

Development of Dipeptidic hGPR54 Agonists
A series of dipeptides were designed as potential agonists of the human KiSS1-derived peptide receptor (hGPR54). While the sequence Arg-Trp-NH2was the most efficient in terms of affinity, we established a convergent synthetic strategy to optimi
Doebelin, Christelle,Bertin, Isabelle,Schneider, Séverine,Schmitt, Martine,Bourguignon, Jean-Jacques,Ancel, Caroline,Simonneaux, Valerie,Simonin, Frédéric,Bihel, Frédéric
supporting information
p. 2147 - 2154
(2016/11/04)

Surface-exposed Pd nanoparticles supported over nanoporous carbon hollow tubes as an efficient heterogeneous catalyst for the C[sbnd]C bond formation and hydrogenation reactions
Designing uniformly dispersed Pd nanoparticles over nanoporous carbon supports is very demanding in the context of heterogeneous catalysis. However in most of the cases cluster/agglomerated Pd particles are formed over carbon matrixes, which lack sufficient stability and formation of a sustainable passive layer that can prevent the direct contact between the active metal sites with the reactants. Herein we report the in-situ preparation of surface-exposed Pd nanoparticle over N-doped carbon hollow tubes i.e. Pd@CHT, which showed high catalytic activity compared with agglomerated Pd on carbon. The simplicity in the preparation of Pd@CHT via one step direct carbonization of hypercrosslinked polymer tubes followed by reduction in the presence of NaBH4 can offer huge potential in liquid phase heterogeneous catalysis. High dispersibility of the catalyst in the reaction medium, good stability and reusability of Pd@CHT is observed for the Sonogashira, cyanation and hydrogenation reactions for the synthesis of a wide range of value added fine chemicals, suggesting its future potential in heterogeneous catalysis.
Modak, Arindam,Bhaumik, Asim
p. 147 - 156
(2016/10/30)

Method for synthesizing multi-substituted alkyne
The invention discloses a method for synthesizing multi-substituted alkyne, relates to the technical field of synthesis of multi-substituted alkyne and provides a method for synthesizing multi-substituted alkyne through terminal alkyne and halide of sp2 type carbon under the catalysis of a polyaniline supported nano-palladium catalyst. According to the method, polyaniline supported nano-palladium is taken as a catalyst, diisopropyl-2-ethyoxyl ethylamine is taken as alkali, and multi-substituted alkyne is directly synthesized in one step through cross coupling. Compared with conventional methods, the method has the advantages that raw materials are simple and easy to obtain, the cost is low, the catalyst is mild, environment-friendly and rich, and a solvent is clean and environment-friendly. Thus, a clean and practical synthesis method is provided for synthesis of such important compounds.
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Paragraph 0012; 0013; 0022; 0023

(2016/11/24)

An efficient mesoporous carbon nitride (g-C3N4) functionalized Pd catalyst for carbon-carbon bond formation reactions
Metal nanoparticles in pristine form without any stabilizing agents and free from agglomeration are very critical for their function and diverse catalytic applications. With the goal to accomplish a molecularly defined Pd-based heterogeneous C-C bond form
Elavarasan,Baskar,Senthil,Bhanja, Piyali,Bhaumik,Selvam,Sasidharan
p. 49376 - 49386
(2016/06/15)

Antibacterial agents
no abstract published
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Paragraph 0192; 0193

(2015/09/22)

Tetragonal Cu2Se nanoflakes: Synthesis using selenated propylamine as Se source and activation of Suzuki and Sonogashira cross coupling reactions
The metastable tetragonal Cu2Se phase as nanoflakes has been synthesized for the first time by treating CuCl2 taken in a mixture (1:1) of 1-octadecene and oleylamine with H2N-(CH2)3-SePh dissolved in
Singh, Ved Vati,Singh, Ajai Kumar
p. 725 - 732
(2015/02/19)

Nickel(II) complexes containing ONS donor ligands: Synthesis, characterization, crystal structure and catalytic application towards C-C cross-coupling reactions
Nickel(II) complexes containing thiosemicarbazone ligands [Ni(L)2] (1-3) (L = 9,10-phenanthrenequinonethiosemicarbazone (HL1), 9,10-phenanthrenequinone-N-methylthio semicarbazone (HL2) and 9, 10-phenanthrenequinone-N-phenylthiosemicarbazone (HL3)) have been synthesized and characterized by elemental analysis and spectroscopic (IR, UV-Vis, 1H, 13C-NMR and ESI mass) methods. The molecular structures of complexes 1 and 2 were identified by means of single-crystal X-ray diffraction analysis. The analysis revealed that the complexes possess a distorted octahedral geometry with the ligand coordinating in a uni-negative tridentate ONS fashion. The catalytic activity of complexes towards some C-C coupling reactions (viz., Kumada-Corriu, Suzuki-Miyaura and Sonogashira) has been examined. The complexes behave as efficient catalysts in the Kumada-Corriu and Sonogashira coupling reactions rather than Suzuki-Miyaura coupling. [Figure not available: see fulltext.]
Anitha, Panneerselvam,Manikandan, Rajendran,Vijayan, Paranthaman,Prakash, Govindan,Viswanathamurthi, Periasamy,Butcher, Ray Jay
p. 597 - 608
(2015/06/17)

Pd doped SiO2 nanoparticles: An efficient recyclable catalyst for Suzuki, Heck and Sonogashira reactions
Palladium doped silica (Pd/SiO2) mesoporous material was synthesized via the sol-gel route using the P123 triblock copolymer as a structure directing agent. Pd/SiO2 was efficiently used as a catalyst for Suzuki, Heck and Sonogashira reactions under microwave irradiation. The catalyst exhibited high activity for all the coupling reactions and can be recycled nine times without a significant loss in its catalytic activity. This journal is the Partner Organisations 2014.
Kotadia, Deepali A.,Patel, Urmila H.,Gandhi, Sahaj,Soni, Saurabh S.
p. 32826 - 32833
(2014/08/18)

Palladium-poly(3-aminoquinoline) hollow-sphere composite: Application in sonogashira coupling reactions
We report on the use of palladium acetate for the synthesis of a palladium-based polymer composite material as a catalyst for Sonogashira cross-coupling reactions for aryl and heteroaryl of iodides and bromides.
UlIslam, Rafique,Mahato, Sanjit K.,Shukla, Sudheesh K.,Witcomb, Michael J.,Mallick, Kaushik
p. 2453 - 2461
(2013/08/23)

Regioselectivity of Larock heteroannulation: A contribution from electronic properties of diarylacetylenes
A series of 2,3-diarylindoles were synthesized from 2-iodoaniline and unsymmetrical diarylacetylenes using the Larock heteroannulation. Diarylacetylenes bearing electron-withdrawing substituents lead to 2,3-diarylindoles with substituted phenyl moieties at the 2-position as major products, while those with electron-donating groups preferably yield indole products with substituted phenyl moieties at the 3-position. The regioisomeric product ratios exhibit a clear correlation with Hammett σp values. DFT calculations reveal the origin of this effect, displaying smaller activation energy barriers for those pathways leading to the major regioisomer.
Phetrak, Nared,Rukkijakan, Thanya,Sirijaraensre, Jakkapan,Prabpai, Samran,Kongsaeree, Palangpon,Klinchan, Chayada,Chuawong, Pitak
p. 12703 - 12709
(2014/01/17)

Exploring the UDP pocket of LpxC through amino acid analogs
Lipopolysaccharide (LPS) biosynthesis is an attractive antibacterial target as it is both conserved and essential for the survival of key pathogenic bacteria. Lipid A is the hydrophobic anchor for LPS and a key structural component of the outer membrane of Gram-negative bacteria. Lipid A biosynthesis is performed in part by a unique zinc dependent metalloamidase, LpxC (UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase), which catalyzes the first non-reversible step in lipid A biosynthesis. The UDP portion of the LpxC substrate-binding pocket has been relatively unexplored. We have designed and evaluated a series of hydroxamate based inhibitors which explore the SAR of substitutions directed into the UDP pocket with a range of substituted α-amino acid based linkers. We also provide the first wild type structure of Pseudomonas aeruginosa LpxC which was utilized in the design of many of these analogs.
Hale, Michael R.,Hill, Pamela,Lahiri, Sushmita,Miller, Matthew D.,Ross, Philip,Alm, Richard,Gao, Ning,Kutschke, Amy,Johnstone, Michele,Prince, Bryan,Thresher, Jason,Yang, Wei
p. 2362 - 2367
(2013/05/09)

Silver(i)-catalyzed carboxylation of arylboronic esters with CO2
A variety of arylboronic esters were efficiently carboxylated with CO 2 using a simple AgOAc/PPh3 catalyst, affording the corresponding carboxylic acids in good yield. This simple and efficient silver(i) catalytic system showed wide functional group compatibility. The Royal Society of Chemistry 2012.
Zhang, Xiao,Zhang, Wen-Zhen,Shi, Ling-Long,Guo, Chun-Xiao,Zhang, Ling-Ling,Lu, Xiao-Bing
supporting information; experimental part
p. 6292 - 6294
(2012/07/16)

Pd-grafted periodic mesoporous organosilica: An efficient heterogeneous catalyst for Hiyama and Sonogashira couplings, and cyanation reactions
The high surface area of 2D-hexagonal periodic mesoporous organosilica (PMO) containing a phloroglucinol-diimine moiety inside the pore wall has been utilized for grafting Pd(ii) at the surface of the mesopores. This Pd-containing PMO material (Pd-LHMS-3) shows excellent catalytic activity in fluoride-free Hiyama cross-coupling reactions in water at alkaline pH conditions. Sonogashira cross-couplings between terminal alkynes and aryl halides take place in the presence of water and hexamine as base in the absence of any Cu co-catalyst. Cyanation of aryl halides is equally promoted with K4[Fe(CN) 6] as the cyanide source (in the absence of poisonous KCN, NaCN or Zn(CN)2) over Pd-LHMS-3. Excellent yield of the products, reusability and the facile work-up could make this Pd-grafted PMO material a unique catalyst for the synthesis of substituted benzonitriles, unsymmetrical biphenyls and di-substituted alkynes under environmentally benign reaction conditions. Further good yield of products and no evidence of leached Pd from the catalyst surface during the reaction and its smooth recovery confirm the true heterogeneity in these catalytic reactions.
Modak, Arindam,Mondal, John,Bhaumik, Asim
p. 2840 - 2855
(2012/11/07)

Piperazine-2,3-dicarboxylic acid derivatives as dual antagonists of NMDA and GluK1-containing kainate receptors
Competitive N-methyl-d-aspartate receptor (NMDAR) antagonists bind to the GluN2 subunit, of which there are four types (GluN2A-D). We report that some N1-substituted derivatives of cis-piperazine-2,3-dicarboxylic acid display improved relative
Irvine, Mark W.,Costa, Blaise M.,Dlaboga, Daniel,Culley, Georgia R.,Hulse, Richard,Scholefield, Caroline L.,Atlason, Palmi,Fang, Guangyu,Eaves, Richard,Morley, Richard,Mayo-Martin, Maria B.,Amici, Mascia,Bortolotto, Zuner A.,Donaldson, Lucy,Collingridge, Graham L.,Molnár, Elek,Monaghan, Daniel T.,Jane, David E.
p. 327 - 341
(2012/03/11)

Copper and amine free Sonogashira cross-coupling reaction catalyzed by efficient diphosphane-palladium catalyst
The commercially available diphosphane ligand MeO-BIPHEP was first investigated in the palladium-catalyzed Sonogashira reaction in the absence of copper and amine. The coupling of various aryl bromides and aryl chlorides with phenylacetylene gave moderate
He, Ting,Wu, Lei Lei,Fu, Xing Li,Fu, Hai Yan,Chen, Hua,Li, Rui Xiang
experimental part
p. 1175 - 1178
(2012/01/05)

Copper-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with aryl halides
The copper-catalyzed decarboxylative reactions of alkynyl carboxylic acids with aryl halides were performed under relatively mild reaction conditions. Benzofurans could be further prepared smoothly by a one-pot domino protocol on the basis of decarboxylative cross-coupling of 2-iodophenol.
Zhao, Dongbing,Gao, Chao,Su, Xiaoyu,He, Yunqing,You, Jingsong,Xue, Ying
supporting information; experimental part
p. 9049 - 9051
(2011/02/17)

Solid-phase synthesis of 1,2-diketones via acetylene oxidation: A versatile diversity platform for the combinatorial synthesis of heterocycles
Investigations towards the solid-phase synthesis of 1,2-diketones via the oxidation of acetylenes and their use in the combinatorial synthesis of heterocycles such as imidazoles and quin-oxalines are described. Georg Thieme Verlag Stuttgart New York.
Griebenow, Nils,Meyer, Thorsten
experimental part
p. 2639 - 2643
(2010/11/18)

Synthesis and characterization of a polymer-anchored palladium(II) Schiff base complex and its catalytic efficiency in phosphine-free Sonogashira coupling reactions
A polymer-anchored Pd(II) Schiff base complex has been synthesized by reacting a polymeric amine with 2-pyridinecarboxaldehyde to get the polymer-anchored Schiff base, which was then reacted with palladium acetate. The catalyst was characterized by physicochemical and spectroscopic methods. It shows excellent catalytic activity in the Sonogashira coupling of phenylacetylene with aryl halides using triethylamine as a base and copper iodide as a co-catalyst in water under open air at 70 °C. We have also studied the effects of base and solvent on the coupling reaction. Sonogashira reactions of phenylacetylene with a variety of functionalized aryl halides were performed under the optimized reaction conditions. This catalyst gives excellent yields without the use of phosphine ligands. Further experiments showed that the catalyst can be used five times without much loss in the catalytic activity. Springer Science+Business Media B.V. 2010.
Islam,Mondal, Sanchita,Roy, Anupam Singha,Mondal, Paramita,Mobarak, Manir,Hossain, Dildar,Pandit, Palash
experimental part
p. 305 - 313
(2011/11/06)

Discovery of a potent and brain penetrant mGluR5 positive allosteric modulator
This Letter describes the discovery of a novel series of mGluR5 positive allosteric modulators (PAMs). The lead compound, 11c, exhibits excellent potency (EC50 = 30 nM) in vitro, and reaches high brain levels in both rats and mice after oral ad
Ritzen, Andreas,Sindet, Rikke,Hentzer, Morten,Svendsen, Nannette,Brodbeck, Robbin M.,Bundgaard, Christoffer
supporting information; experimental part
p. 3275 - 3278
(2010/03/24)

Copper(I)-catalyzed carboxylation of aryl- and alkenylboronic esters
(Chemical Equation Presented) The copper(I)-catalyzed carboxylation reaction of aryl- and alkenylboronic esters proceeded smoothly under CO 2 to give the corresponding carboxylic acid in good yield. This reaction showed wide generality with higher functional group tolerance compared to the corresponding Rh(I)-catalyzed reaction.
Takaya, Jun,Tadami, Satoshi,Ukai, Kazutoshi,Iwasawa, Nobuharu
supporting information; experimental part
p. 2697 - 2700
(2009/05/26)

ANTIBACTERIAL AGENTS
Antibacterial compounds of formula (I) are provided, as well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.
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Page/Page column 86-87

(2009/01/24)

HYDANTOIN DERIVATIVES USEFUL AS ANTIBACTERIAL AGENTS
This invention relates to compounds of the Formula (I): or a pharmaceutically acceptable salt, solvate, ester or isomer thereof, which is useful for the treatment of diseases or conditions mediated by LpxC.
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Page/Page column 53

(2008/06/13)

Recyclable polymer bound Pd(O) phosphine catalyst for effecting sp 2-sp2 and sp2-sp carbon-carbon coupling reactions in aqueous medium
Aqueous Heck type coupling reactions between aryl iodides and terminal alkenes or alkynes have been effected in good yields using a recyclable catalyst system that consists of poly(N-isopropyl acrylamide) bound Pd(O) phosphine and an anionic surfactant, potassium lauryl sulphate.
Koshti, Nirmal,Parab, Bharat,Naik, Shubhangi
p. 154 - 159
(2008/02/09)

A simple and efficient copper-free catalytic system based on a palladacycle for the arylation of alkynes
The palladacycle [Pd(k2-C,N-C=(C6H 5)C(Cl)CH2NMe2)(μ-Cl)]2 (1) derived from the chloropalladation of 3-(dimethylamino)-1-phenyl-1-propyne and its phosphine adduct [Pd(k2-C,N-C=(C6H5)C(Cl) CH2NMe2)P(4-CF3C6H4) 3(Cl)] (3) promote the alkynylation of bromo- and iodoarenes under relatively mild reaction conditions. The coupling of iodoarenes and activated bromoarenes with terminal alkynes can be conducted at room temperature. Turnover numbers have been achieved up to 105 with iodoarenes and up to 94 for deactivated bromoarenes but at higher temperatures (120°C). Selective poisoning experiments (Hg, Collman and Crabtree tests) suggest that soluble Pd(0) species are the most probable catalytically active species involved in this Csp2-Csp coupling reaction.
Consorti, Crestina S.,Flores, Fabricio R.,Rominger, Frank,Dupont, Jairton
p. 133 - 141
(2007/10/03)

General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water
Amphiphilic phosphine ligands (see structures; Cy = cyclohexyl) were prepared and utilized in palladium-catalyzed Suzuki-Miyaura and Sonogashira coupling reactions in water or water/organic biphasic solvents, providing excellent yields of functionalized b
Anderson, Kevin W.,Buchwald, Stephen L.
p. 6173 - 6177
(2007/10/03)

Aqueous-phase, palladium-catalyzed cross-coupling of aryl bromides under mild conditions, using water-soluble, sterically demanding alkylphosphines
Sterically demanding, water-soluble alkylphosphines have been used in combination with various palladium salts in Suzuki, Sonogashira, and Heck couplings of aryl bromides under mild conditions in aqueous solvents. The tert-butyl-substituted ligands 2-(di-tert-butylphosphino)ethyltrimethylammonium chloride (t-Bu-Amphos) and 4-(di-tert-butylphosphino)-N,N-dimethylpiperidinium chloride (t-Bu-Pip-phos) in combination with palladium(II) salts were found to give catalysts that were significantly more active than catalysts derived from tri(3-sulfonatophenyl)phosphine trisodium (TPPTS). Suzuki couplings of unactivated aryl bromides occurred efficiently at room temperature in water/acetonitrile and water/toluene biphasic mixtures or in neat water. Notably, Suzuki couplings of hydrophilic aryl bromides gave high yields without using organic solvents for the reaction or purification. This methodology has been applied to a highly efficient synthesis of diflunisal. The catalyst derived from t-Bu-Amphos was recycled three times in Suzuki couplings in water/toluene before catalyst activity began to significantly drop. The average yield of four cycles was >80% per cycle. Heck and Sonogashira couplings were carried out under mild conditions (50 and 80°C, respectively) with unactivated aryl bromides to give coupled products in high yield.
DeVasher, Rebecca B.,Moore, Lucas R.,Shaughnessy, Kevin H.
p. 7919 - 7927
(2007/10/03)

Chemical compounds
Provided herein are novel and useful compounds having a tryptase inhibition activity, pharmaceutical compositions comprising such compounds, and methods treating subjects suffering from a condition, disease, or disorder that can be ameliorated by the administration of an inhibitor of tryptase, e.g., asthma and inflammatory diseases, to name only a few.
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(2008/06/13)

A novel microwave-activated Sonogashira coupling reaction and cleavage using polyethylene glycol as phase-transfer catalyst and polymer support
Under microwave-activation polyethylene glycol bound 4-iodobenzoic acid could be readily reacted with various terminal alkynes in excellent yields and purity using polyethylene glycol (PEG) as a solid-liquid phase-transfer catalyst and polymer support; the cleavage could be dramatically accelerated under microwave activation.
Xia, Min,Wang, Yan-Guang
p. 173 - 175
(2007/10/03)

Cross-coupling of aryl iodides with paramagnetic terminal acetylenes derived from 4,4,5,5-tetramethyl-2-imidazoline-2-oxyl 3-oxide
2-(Arylylethynylphenyl)-4,4,5,5-tetramethyl-2-imidazoline-1-oxyl 3-oxides 12 and 13 were synthesized by cross-coupling of aryl iodides with 1-alkynes containing the 4,4,5,5-tetramethyl-2-imidazoline-1-oxyl 3-oxide fragment. A procedure was developed for the preparation of 3-and 4-ethynyibenzaldehydes with the use of 2-methylbut-3-yn-2-ol.
Klyatskaya, S. V.,Tretyakov, E. V.,Vasilevsky, S. F.
p. 128 - 134
(2007/10/03)

Copper-catalysed cross coupling reaction under microwave irradiation conditions
Copper-catalysed cross coupling of aryl iodies with terminal alkynes was readly achieved using Cul-PPh3 as catalyst in the presence of potassium carbonate in DMF at 375W for 10 minutes under microwave irradiation.
Wang,Hu,Wei
p. 536 - 537
(2007/10/03)

Catalytic coupling of terminal acetylenes with iodoarenes and diaryliodonium salts in water
The catalytic coupling of terminal acetylenes with iodoarenes and diaryliodonium salts are shown to occur in aqueous K2CO3 in the presence of 10 mol.% Bu3N under very mild conditions using PdCl2(PPh3)2 and CuI as catalyst precursor to give substituted tolans in high yields.
Bumagin, Nikolai A.,Sukhomlinova, Ludmila I.,Luzikova, Elena V.,Tolstaya, Tatiana P.,Beletskaya, Irina P.
p. 897 - 900
(2007/10/03)

Palladium-Catalyzed Condensation of Aryl Iodides and Diaryl Iodonium Salts with Terminal Acetylenes in Aqueous Medium
Aryl iodides and aryliodonium salts readily react with terminal acetylenes in water in the presence of catalytic amounts of PdCl2(PPh3)2, CuI, and Bu3N to give diarylacetylenes with quantitative yields.
Bumagin,Sukhomlinova,Luzikova,Tolstaya,Beletskaya
p. 996 - 1000
(2007/10/03)

HECK REACTIONS IN SOLID PHASE SYNTHESIS
Heck reactions of polymer bound aryl iodide (1) or styrene (2) with olefins or aryl halides generally gave good yields of products of high purity.The methodology developed can be applied as a convenient procedure for generating 1,2-disubstituted olefins i
Yu, Kuo-Long,Deshpande, Milind S.,Vyas, Dolatrai M.
p. 8919 - 8922
(2007/10/02)

CROSS-COUPLING OF TERMINAL ACETYLENES WITH ORGANIC HALIDES IN THE R3N-CuI-Pd SYSTEM
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Bumagin, N. A.,Ponomarev, A. B.,Beletskaya, I. P.
p. 1433 - 1438
(2007/10/02)