- Zeolitic imidazolate frameworks-67 (ZIF-67) supported PdCu nanoparticles for enhanced catalytic activity in Sonogashira-Hagihara and nitro group reduction under mild conditions
-
A bimetallic PdCu supported on amine functionalized ZIF-67 is shown to be efficient catalyst in Sonogashira-Hagihara coupling reaction of aryl iodides at room temperature and aryl bromides at 40 oC. In addition, the catalyst is used in the reduction of 4-
- Gholinejad, Mohammad,Naghshbandi, Zhwan,Sansano, Jose M.
-
-
- Copper-Catalyzed Cross-Nucleophile Coupling of β-Allenyl Silanes with Tertiary C-H Bonds: A Radical Approach to Branched 1,3-Dienes
-
Described herein is a distinctive approach to branched 1,3-dienes through oxidative coupling of two nucleophilic substrates, β-allenyl silanes, and hydrocarbons appending latent functionality by copper catalysis. Notably, C(sp3)-H dienylation proceeded in a regiospecific manner, even in the presence of competitive C-H bonds that are capable of occurring hydrogen atom transfer process, such as those located at benzylic and other tertiary sites, or adjacent to an oxygen atom. Control experiments support the intermediacy of functionalized alkyl radicals.
- Shan, Qi-Chao,Hu, Lu-Min,Qin, Wei,Hu, Xu-Hong
-
supporting information
p. 6041 - 6045
(2021/08/03)
-
- Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde
-
A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and good tolerance of various substituents make it an alternative approach to previous protocols, and potential applications of these investigated compounds are expected with or without post-modifications.
- Chen, Xiaojuan,Fu, Liping,Huo, Xiaoli,Shao, Jiaan,Yu, Liya,Zeng, Linghui,Zhang, Chong,Zhang, Jiankang,Zhu, Huajian
-
supporting information
p. 16430 - 16433
(2021/10/01)
-
- Regioselective Iron-Catalysed Cross-Coupling Reaction of Aryl Propargylic Bromides and Aryl Grignard Reagents
-
An iron-catalysed Kumada-type cross-coupling reaction between aryl substituted propargylic bromides and arylmagnesium reagents has been developed. Propargylic coupling products were the main or only outcome, and propargyl/allene regioselectivity was shown to depend on the electronic nature of the substituents on the triple bond of the substrate and on the arylmagnesium halide. Best selectivities were observed when electron donating substituents were present in either reagent. The process is stereoespecific, occurs with configuration inversion and no carbon-based radicals seem to be involved in the mechanism. (Figure presented.).
- Manjón-Mata, Inés,Quirós, M. Teresa,Bu?uel, Elena,Cárdenas, Diego J.
-
supporting information
p. 146 - 151
(2019/12/11)
-
- Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition
-
Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity.
- Baek, Seung-Yeol,Baik, Mu-Hyun,Choe, Wonyoung,Hong, Sung You,Jeon, Ji Hwan,Jeong, Seo Yeong,Kim, Woo Gyum,Nam, Dongsik
-
supporting information
p. 3374 - 3381
(2020/05/14)
-
- Catalytic Access to Functionalized Allylic gem-Difluorides via Fluorinative Meyer–Schuster-Like Rearrangement
-
An unprecedented approach for efficient synthesis of functionalized allylic gem-difluorides via catalytic fluorinative Meyer–Schuster-like rearrangement is disclosed. This transformation proceeded with readily accessible propargylic fluorides, and low-cost B–F reagents and electrophilic reagents by sulfide catalysis. A series of iodinated, brominated, and trifluoromethylthiolated allylic gem-difluorides that were difficult to access by other methods were facilely produced with a wide range of functional groups. Importantly, the obtained iodinated products could be incorporated into different drugs and natural products, and could be expediently converted into many other valuable gem-difluoroalkyl molecules as well. Mechanistic studies revealed that this reaction went through a regioselective fluorination of alkynes followed by a formal 1,3-fluorine migration under the assistance of the B–F reagents to give the desired products.
- An, Rui,Li, Huimin,Liao, Lihao,Wu, Jin-Ji,Xu, Yang,Zhao, Xiaodan
-
supporting information
p. 11010 - 11019
(2020/05/18)
-
- Integrating Reactors and Catalysts through Three-Dimensional Printing: Efficiency and Reusability of an Impregnated Palladium on Silica Monolith in Sonogashira and Suzuki Reactions
-
For this work, an integrated system composed of a polypropylene reactor and a palladium on silica monolithic catalyst was designed and manufactured by 3D-printing. These devices are able to perform solution phase chemistry in a robotic orbital shaker. The capped reactor was obtained in its entirety by 3D-printing, using polypropylene and fused deposition modeling. The monolithic catalyst was also obtained by 3D-printing -robocasting- of a silica support, sintering and subsequent palladium deposition through the wet impregnation method. The catalytic efficiency in Sonogashira or Suzuki reactions as well as the recyclability of the entire system – catalyst+reactor – were studied. The strong electrostatic adsorption (SEA) of the palladium on sintered silica and the reduced mechanical stress produced by the convenient adjustment of the catalyst into the polypropylene reactor makes the catalytic system reusable without significant loss of catalytic activity.
- Díaz-Marta, Antonio S.,Ya?ez, Susana,Lasorsa, Eliana,Pacheco, Patricia,Tubío, Carmen R.,Rivas, José,Pi?eiro, Yolanda,Gómez, Manuel A. Gonzalez,Amorín, Manuel,Guitián, Francisco,Coelho, Alberto
-
p. 1762 - 1771
(2020/02/15)
-
- Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines
-
A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.
- Chen, Zhengwang,Liang, Pei,Ma, Xiaoyue,Luo, Haiqing,Xu, Guohai,Liu, Tanggao,Wen, Xiaowei,Zheng, Jing,Ye, Hui
-
supporting information
p. 1630 - 1639
(2019/01/26)
-
- Metal-free aminothiation of alkynes: Three-component tandem annulation toward indolizine thiones from 2-alkylpyridines, ynals, and elemental sulfur
-
A metal-free three-component annulation reaction for the synthesis of indolizine thiones via tandem C-C/C-N/C-S bond formation was developed. Various 2-alkylpyridines with aromatic ynals and elemental sulfur proceeded smoothly under catalyst-free conditions, and the desired products were obtained in moderate to excellent yields.
- Chen, Zhengwang,Liang, Pei,Xu, Fan,Deng, Zhen,Long, Lipeng,Luo, Guotian,Ye, Min
-
supporting information
p. 12639 - 12647
(2019/10/11)
-
- Construction of All-Carbon Quaternary Stereocenters by Palladium-Catalyzed Decarboxylative Propargylation
-
A method for the construction of chiral quaternary stereocenters has been accomplished via decarboxylative palladium-catalyzed propargylic alkylation. Both pressurized sealed tubes and microwave irradiation have proven successful for this transformation, yet despite these forcing conditions a range of α-aryl,α-propargyl, and α-alkyl,α-propargyl containing all-carbon quaternary products have been synthesized in good yields and high enantioselectivities (up to 92:8 er). While palladium-catalyzed decarboxylative allylic alkylation has been well studied, this work represents the furthest advancement for the propargylic variant to date.
- O'Broin, Calvin Q.,Guiry, Patrick J.
-
supporting information
p. 5402 - 5406
(2019/08/01)
-
- Comparison between Conventional and Nonconventional Methods for the Synthesis of Some 2-Oxazolidinone Derivatives and Preliminary Investigation of Their Inhibitory Activity Against Certain Protein Kinases
-
A series of propargyl and allyl carbamates were prepared directly from propargyl and allyl alcohols and phenyl or cyclohexyl isocyanate or indirectly by generating the isocyanates in situ from the corresponding Cbz-protected amines. The obtained carbamate
- Ziane,Mazari,Safer,Sad El Hachemi Amar,Ruchaud,Baratte,Bach
-
p. 1061 - 1069
(2019/09/06)
-
- Palladium-Catalyzed Nitrile-Assisted C(sp3)-Cl Bond Formation for Synthesis of Dichlorides
-
A palladium-catalyzed coupling procedure of alkenes with alkynylnitriles has been demonstrated for the synthesis of dichlorides. The reaction is the first example of nitrile-assisted C(sp3)-Cl formation promoted by coordination of a cyano group with an alkylpalladium(II) complex. The construction of a five-membered cycle intermediate successfully inhibits the β-hydride abstraction, resulting in direct C-Cl bond reductive elimination of alkylpalladium(II) chloride.
- He, Dandan,Huang, Liangbin,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
-
supporting information
p. 8308 - 8311
(2019/10/16)
-
- Bi(OTf)3 catalyzed synthesis of acyclic β-sulfanyl ketones via a tandem Meyer-Schuster rearrangement/conjugate addition reaction
-
A new strategy to prepare acyclic β-carbonyl thioethers from propargyl alcohols and sulfur nucleophiles is reported. The investigation of the reaction substrates scope indicated that primary 3-aryl propargyl alcohols and thiols underwent the transformation smoothly. The reaction probably proceeded a Bi(OTf)3-catalyzed tandem Meyer-Schuster rearrangement of 3-aryl propargyl alcohol, followed by a thiol Michael conjugate addition of thiols to in situ generated α, β-unsaturated ketones. The method was 100% atom economic, high-yielding, and easy to handle, making it a valuable method for the construction of β-carbonyl sulfides.
- Wang, Yuan,Yin, Yan,Zhang, Qinglin,Pan, Wanyong,Guo, Huifeng,Pei, Keke
-
supporting information
p. 2030 - 2034
(2019/07/03)
-
- Efficient 1,3-Oxazolidin-2-one Synthesis through Heterogeneous PdII-Catalyzed Intramolecular Hydroamination of Propargylic Carbamates
-
Herein, we present an operationally simple protocol for the cycloisomerization of propargylic carbamates in which a heterogeneous catalyst consisting of Pd species immobilized on amino-functionalized siliceous mesocellular foam (PdII-AmP-MCF) i
- Oschmann, Michael,Placais, Clotilde,Nagendiran, Anuja,B?ckvall, Jan-E.,Verho, Oscar
-
supporting information
p. 6295 - 6299
(2019/05/08)
-
- Visible-Light-Assisted Cobalt-2-(hydroxyimino)-1-phenylpropan-1-one Complex Catalyzed Pd/Cu-Free Sonogashira–Hagihara Cross-Coupling Reaction
-
An effective and inexpensive strategy for the Co(C9H9NO2)3 catalyzed Sonogashira–Hagihara cross-coupling reaction of aryl bromides containing electron-rich and electron-poor substituents with terminal alkynes wa
- Song, Jin-Yi,Zhou, Xuan,Song, He,Liu, Yang,Zhao, Hong-Yan,Sun, Zhi-Zhong,Chu, Wen-Yi
-
p. 758 - 762
(2018/01/27)
-
- Copper-catalyzed [1,2]-rearrangements of allylic iodides and aryl α-diazoacetates
-
The [1,2]- and [2,3]-rearrangements of iodonium ylides are synthetically useful reactions for the generation of functionalized α-iodoesters. Allylic iodides are coupled with α-diazoesters in the presence of a copper catalyst and a ligand to generate iodonium ylides, which undergo metal-mediated rearrangements. By fine-tuning the structure of the ligand, we have reversed the regioselectivity of copper-catalyzed reactions of iodonium ylides from [2,3]- to [1,2]-rearrangements with the use of alternate bipyridine ligands. The preference for [1,2]-rearrangements was further improved by using bulky aryl α-diazoester substrates. Several α-iodoesters with a diverse range of functional groups were generated in good yields (up to 88% yield) and high regioselectivities (up to >95:5 regioisomeric ratio). A deuterium-labeled substrate was utilized to gain insight into the mechanism of the reaction.
- Xu, Bin,Gartman, Jackson A.,Tambar, Uttam K.
-
p. 4150 - 4159
(2017/06/29)
-
- Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes with Pinacolborane
-
We report a cobalt-catalyzed asymmetric hydroboration/cyclization of 1,6-enynes with catalysts generated from Co(acac)2 and chiral bisphosphine ligands and activated in situ by reaction with pinacolborane (HBpin). A variety of oxygen-, nitrogen
- Yu, Songjie,Wu, Caizhi,Ge, Shaozhong
-
supporting information
p. 6526 - 6529
(2017/05/29)
-
- Design and synthesis of novel xanthine derivatives as potent and selective A2B adenosine receptor antagonists for the treatment of chronic inflammatory airway diseases
-
Adenosine induces bronchial hyperresponsiveness and inflammation in asthmatics through activation of A2B adenosine receptor (A2BAdoR). Selective antagonists have been shown to attenuate airway reactivity and improve inflammatory cond
- Basu, Sujay,Barawkar, Dinesh A.,Ramdas, Vidya,Patel, Meena,Waman, Yogesh,Panmand, Anil,Kumar, Santosh,Thorat, Sachin,Naykodi, Minakshi,Goswami, Arnab,Reddy, B. Srinivasa,Prasad, Vandna,Chaturvedi, Sandhya,Quraishi, Azfar,Menon, Suraj,Paliwal, Shalini,Kulkarni, Abhay,Karande, Vikas,Ghosh, Indraneel,Mustafa, Syed,De, Siddhartha,Jain, Vaibhav,Banerjee, Ena Ray,Rouduri, Sreekanth R.,Palle, Venkata P.,Chugh, Anita,Mookhtiar, Kasim A.
-
p. 218 - 229
(2017/04/19)
-
- Sodium Phenoxide Mediated Hydroxymethylation of Alkynylsilanes with N-[(Trimethylsiloxy)methyl]phthalimide
-
The hydroxymethylation of alkynylsilanes with formaldehyde generated in situ from N-[(trimethylsiloxy)methyl]phthalimide proceeds in the presence of a stoichiometric amount of NaOPh. The reaction occurs at room temperature by using an operationally simple one-step procedure. A variety of alkynylsilanes possessing electron-donating, electron-withdrawing, and halogen groups (including heteroaryl-substituted alkynylsilanes) provide hydroxymethylated products.
- Asano, Narumi,Sasaki, Keita,Chataigner, Isabelle,Shigeno, Masanori,Kondo, Yoshinori
-
supporting information
p. 6926 - 6930
(2017/12/26)
-
- Fe(OTf)3-catalyzed tandem Meyer-Schuster rearrangement/intermolecular hydroamination of 3-aryl propargyl alcohols for the synthesis of acyclic β-Aminoketones
-
Fe(OTf)3-catalyzed synthesis of acyclic β-aminoketones from 3-aryl propargyl alcohols and nitrogen nucleophiles were investigated. Results showed that propargyl alcohols without bulky groups α to the hydroxyl group underwent the transformation smoothly. Sulphonamides exhibited the higher reactivity than amides as the nitrogen nucleophiles and the transformation of acyclic β-aminoketones were finished in shorter reaction time and higher yields. Finally, racemic fluoxetine was efficiently accessed with the present reaction as the first step. This novel synthesis of acyclic β-aminoketones probable proceeded a Fe(OTf)3-catalyzed Meyer-Schuster rearrangement of 3-aryl propargyl alcohols, followed by a intermolecular hydroamination between nitrogen nucleophiles and α, β-unsaturated ketones.
- Tao, Ruiheng,Yin, Yan,Duan, Yongbin,Sun, Yuxing,Sun, Yue,Cheng, Fengkai,Pan, Jinpeng,Lu, Cheng,Wang, Yuan
-
p. 1762 - 1768
(2017/03/08)
-
- Squaramide catalyzed enantioselective iodolactonization of allenoic acids
-
An asymmetric iodolactonization reaction of allenoic acids has been extensively studied. Eight different chiral squaramides were prepared in a straightforward manner and investigated as organocatalysts. The reaction protocol is operationally simple to exe
- Kristianslund, Renate,Aursnes, Marius,Tungen, J?rn Eivind,Hansen, Trond Vidar
-
supporting information
p. 5232 - 5236
(2016/11/13)
-
- Ligand-Controlled Regiodivergence in the Copper-Catalyzed [2,3]- and [1,2]-Rearrangements of Iodonium Ylides
-
Despite the importance of allylic ylide rearrangements for the synthesis of complex molecules, the catalyst control of [2,3]- and [1,2]-rearrangements remains an unsolved problem. We developed the first regiodivergent [2,3]- and [1,2]-rearrangements of iodonium ylides that are controlled by copper catalysts bearing different ligands. In the presence of a 2,2′-dipyridyl ligand, diazoesters and allylic iodides react via a [2,3]-rearrangement pathway. Alternatively, a phosphine ligand favors the formation of the [1,2]-rearrangement product. A series of α-iodoesters containing a broad range of functional groups were obtained in high yields, regioselectivities, and diastereoselectivities. Deuterium-labeling studies suggest distinct mechanisms for the regioselective rearrangements.
- Xu, Bin,Tambar, Uttam K.
-
supporting information
p. 12073 - 12076
(2016/09/28)
-
- Palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides
-
A palladium-catalyzed multicomponent reaction (MCR) of propargylic carbonates with isocyanides is reported. Remarkably, the orderly insertion of isocyanides affords two types of valuable N-heterocyclic products (Z)-6-imino-4,6-dihydro-1H-furo[3,4-b]pyrrol-2-amines and (E)-5-iminopyrrolones in high yields. Systematic analysis of the reaction conditions indicates that the selectivity of these N-heterocyclic products can be controlled by ligands and temperature.
- Peng, Jianwen,Gao, Yang,Hu, Weigao,Gao, Yinglan,Hu, Miao,Wu, Wanqing,Ren, Yanwei,Jiang, Huanfeng
-
supporting information
p. 5924 - 5927
(2016/11/29)
-
- Palladium precatalysts containing meta-terarylphosphine ligands for expedient copper-free Sonogashira cross-coupling reactions
-
Three novel palladium complexes utilizing different variations of the evolutionary meta-terarylphosphine ligand, CyPhine, were developed. These air- and moisture-stable complexes, PdCl2L2 (L = CyPhine, CyPhine-CF3 and CyPhine-nBu), demonstrated exceptional broad-based performance and operational simplicity in the copper-free Sonogashira cross-coupling of challenging (hetero-)aryl chlorides and terminal alkynes. Modifications to the periphery of the ligand scaffold showed modest improvements in the reaction rate when more electron-donating substituents were incorporated, which hints at potential design upgrades in the future.
- Yang, Yong,Lim, Joyce Fen Yan,Chew, Xinying,Robins, Edward G.,Johannes, Charles W.,Lim, Yee Hwee,Jong, Howard
-
p. 3501 - 3506
(2015/07/01)
-
- A versatile and efficient palladium-meta-terarylphosphine catalyst for the copper-free sonogashira coupling of (hetero-)aryl chlorides and alkynes
-
A novel meta-terarylphosphine ligand, CyPhine, was developed and found to be a highly active promoter of copper-free Sonogashira cross-coupling reactions when combined in situ with a palladium source. The evolutionary m-terarylphosphine ligand architectur
- Yang, Yong,Chew, Xinying,Johannes, Charles W.,Robins, Edward G.,Jong, Howard,Lim, Yee Hwee
-
p. 7184 - 7192
(2015/01/16)
-
- Asymmetric nucleophilic monofluorobenzylation of allyl and propargyl halides mediated by a remote sulfinyl group: Synthesis of homoallylic and homopropargylic fluorides
-
Fluorinated 2-(p-tolylsulfinyl)benzyl carbanions react with allyl and propargyl halides in a highly stereoselective way, providing homoallylic and homopropargylic fluorides, respectively, with high optical purity. Theoretical calculations found transition states for these transformations whose relative stabilities are consistent with the experimentally observed stereoselectivity.
- Arroyo, Yolanda,Sanz-Tejedor, M. Ascensión,Parra, Alejandro,Alonso, Inés,García Ruano, José Luis
-
p. 6970 - 6977
(2014/08/18)
-
- A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles
-
A one-pot-three-step method has been developed for the conversion of oxazolino-2H-indazoles into triazolotriazepinoindazolones with three points of diversity. Step one of this process involves a propargyl bromide-initiated ring opening of the oxazolino-2H-indazole (available by the Davis-Beirut reaction) to give an N1-(propargyl)-N2-(2-bromoethyl)-disubstituted indazolone, which then undergoes -CH2Br → -CH2N 3 displacement (step two) followed by an uncatalyzed intramolecular azide-alkyne 1,3-dipolar cycloaddition (step three) to form the target heterocycle. Employing 7-bromooxazolino-2H-indazole allows for further diversification through, for example, palladium-catalyzed coupling chemistry, as reported here.
- Conrad, Wayne E.,Rodriguez, Kevin X.,Nguyen, Huy H.,Fettinger, James C.,Haddadin, Makhluf J.,Kurth, Mark J.
-
supporting information; experimental part
p. 3870 - 3873
(2012/10/07)
-
- Synthesis of trans-A2B2-porphyrins bearing phenylethynyl substituents
-
Efficient and convenient conditions for the preparation of trans-A 2B2-porphyrins bearing two phenylethynyl moieties directly from phenylpropargyl aldehydes and dipyrromethanes of diversified lipophilicity and reactivity have been de
- Nowak-Krol, Agnieszka,Koszarna, Beata,Yoo, Su Yeon,Chrominski, Jan,Weclawski, Marek K.,Lee, Chang-Hee,Gryko, Daniel T.
-
experimental part
p. 2627 - 2634
(2011/06/20)
-
- Selectivity in Garratt-Braverman cyclization: An experimental and computational study
-
Bispropargyl sulfones equipped with aromatic rings of dissimilar nature were synthesized. Under basic conditions, these sulfones isomerized to the bisallenic sulfones, creating a competitive scenario between two alternate Garratt-Braverman (GB) cyclizatio
- Maji, Manasi,Mallick, Dibyendu,Mondal, Sayantan,Anoop, Anakuthil,Bag, Subhendu Sekhar,Basak, Amit,Jemmis, Eluvathingal D.
-
p. 888 - 891
(2011/04/27)
-
- Perfluoro-tagged, phosphine-free palladium nanoparticles supported on silica gel: Application to alkynylation of aryl halides, Suzuki-Miyaura cross-coupling, and Heck reactions under aerobic conditions
-
The utilization of perfluoro-tagged palladium nanoparticles immobilized on fluorous silica gel through fluorous-fluorous interactions (Pd np-A/FSG) or through covalent bonding to silica gel (Pd np-B) in the alkynylation of aryl halides, in the Suzuki-Miyaura cross-coupling, as well as in the Heck reaction between methyl acrylate and aryl iodides is described. The reactions are carried out under aerobic and phosphine-free conditions with excellent to quantitative product yields in each case. The catalysts are easily recovered and reused several times without significant loss of activity. The alkynylation of aryl halides (under copper-free conditions) and the Suzuki-Miyaura cross-coupling are carried out in water. The Heck reaction of methyl acrylate with aryl iodides is best performed in MeCN. The utilization of Pdnp-B in the synthesis of 2,3-disubstituted indoles from 2-(alkynyl)trifluoroacetanilides and aryl halides is also reported.
- Bernini, Roberta,Cacchi, Sandro,Fabrizi, Giancarlo,Forte, Giovanni,Petrucci, Francesco,Prastaro, Alessandro,Niembro, Sandra,Shafir, Alexandr,Vallribera, Adelina
-
supporting information; experimental part
p. 150 - 158
(2010/05/18)
-
- Sonogashira reaction of aryl and heteroaryl halides with terminal alkynes catalyzed by a highly efficient and recyclable nanosized MCM-41 anchored palladium bipyridyl complex
-
A heterogeneous catalyst, nanosized MCM-41-Pd, was used to catalyze the Sonogashira coupling of aryl and heteroaryl halides with terminal alkynes in the presence of CuI and triphenylphosphine. The coupling products were obtained in high yields using low Pd loadings to 0.01 mol%, and the nanosized MCM-41-Pd catalyst was recovered by centrifugation of the reaction solution and re-used in further runs without significant loss of reactivity.
- Lin, Bo-Nan,Huang, Shao-Hsien,Wu, Wei-Yi,Mou, Chung-Yuan,Tsai, Fu-Yu
-
experimental part
p. 9157 - 9173
(2011/02/27)
-
- AMINE COMPOUND AND PHARMACEUTICAL USE THEREOF
-
Provided is a novel amine compound represented by the following formula (I) having a superior peripheral blood lymphocyte decreasing action and superior in the immunosuppressive action, rejection suppressive action and the like, which shows decreased side effects of, for example, bradycardia and the like, or a pharmaceutically acceptable acid addition salt thereof, or a hydrate thereof, or a solvate thereof. wherein each symbol is as defined in the specification.
- -
-
Page/Page column 149-150
(2010/04/25)
-
- Alkynylation of aryl halides with perfluoro-tagged palladium nanoparticles immobilized on silica gel under aerobic, copper- and phosphine-free conditions in water
-
The utilization of perfluoro-tagged palladium nanoparticles immobilized on fluorous silica gel through fluorous-fluorous interactions (Pd np-A/FSG) or linked to silica gel by covalent bonds (Pd np-B) in the alkynylation of terminal a
- Bernini, Roberta,Cacchi, Sandro,Fabrizi, Giancarlo,Forte, Giovanni,Petrucci, Francesco,Prastaro, Alessandro,Niembro, Sandra,Shafir, Alexandr,Vallribera, Adelina
-
supporting information; scheme or table
p. 2270 - 2273
(2009/09/26)
-
- An improved general method for palladium catalyzed alkenylations and alkynylations of aryl halides under microwave conditions
-
Palladium catalyzed facile method for alkenylation and alkynylation of arylhalides in good to excellent yield under microwave condition is reported.
- Togninelli, Andrea,Gevariya, Harsukh,Alongi, Maddalena,Botta, Maurizio
-
p. 4801 - 4803
(2008/02/05)
-
- 3-Aryl-4-Hydroxyfuranone compounds and the human and animal health use thereof
-
The present invention provides a compound of formula I and the use thereof for the inhibition of bacterial cell wall biosynthesis and for the therapeutic treatment of bacterial infection or disease in a patient in need thereof. The present invention also
- -
-
Page/Page column 18
(2008/06/13)
-
- Coupling reactions of aryl bromides with 1-alkynols catalysed by a tetraphosphine/palladium catalyst
-
cis,cis,cis-1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/ [PdCl(C3H5)]2 system catalyses efficiently the coupling reactions of aryl halides with a variety of alkynols such as propargyl alcohol, but-1-yn-4-ol, pent
- Feuerstein, Marie,Doucet, Henri,Santelli, Maurice
-
p. 1603 - 1606
(2007/10/03)
-
- 5,5-Diaryl-2-amino-4-pentenoates as novel, potent, and selective glycine transporter type-2 reuptake inhibitors
-
A novel series of 5,5-diaryl-2-amino-4-pentenoates was synthesized and found to be potent and selective glycine transporter type-2 reuptake inhibitors.
- Isaac, Methvin,Slassi, Abdelmalik,Silva, Kathleen Da,Arora, Jalaj,MacLean, Neil,Hung, Bill,McCallum, Kirk
-
p. 1371 - 1373
(2007/10/03)
-
- Cyclopropanecarboxylic acid alkynyl esters, processes for producing them, and their use as pesticides
-
Cyclopropanecarboxylic acid alkynyl esters of the formula I STR1 wherein R1 is unsubstituted or substituted phenyl or thienyl, R2 is hydrogen, alkyl having 1-6 C atoms, alkenyl having 2-6 C atoms, or phenyl or naphthyl which is unsubstituted or substituted by an alkyl or alkoxy group having 1-2 C atoms or by a halogen atom, and R3 is hydrogen, alkyl having 1-6 C atoms or alkenyl having 2-6 C atoms, are suitable for combating various plant and animal pests, particularly insects, and members of the order Acarina. They can be obtained by reaction of corresponding alkynols with cyclopropanecarboxylic acid or with a reactive functional derivative thereof.
- -
-
-