- A Pd NP-confined novel covalent organic polymer for catalytic applications
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A novel unsymmetrical covalent organic polymer, COP (1), was designed and characterized using several analytical and spectroscopic techniques. COP (1) was synthesized via the nucleophilic substitution reaction of 2,4,6-trichloro-1,3,5-triazine with p-amin
- Yadav, Deepika,Awasthi, Satish Kumar
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p. 1320 - 1325
(2020/02/04)
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- In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor
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A highly efficient and convenient Negishi cross-coupling reaction has been developed for the synthesis of unsymmetrical alkynes and enynes in a continuous-flow process. The reaction proceeds through an in situ generated alkynylzinc reagent by the reaction of lithium acetylide with zinc halide at room temperature followed by a cross-coupling reaction with aryl or vinyl iodides. The notable features of this work compared to the conventional benchtop method are mild reaction conditions, good to excellent yields, broad functional-group compatibility, short residence time (73 sec) and especially desilylation of TMS group with the residence time of only 10.5 sec.
- Kandasamy, Mohanraj,Huang, Yu- Hsuan,Ganesan, Balaji,Senadi, Gopal Chandru,Lin, Wei-Yu
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p. 4349 - 4356
(2019/07/03)
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- Alkyne compound and synthesis method and application thereof
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The invention relates to the field of organic synthesis, in particular to an alkyne compound and a synthesis method and application thereof. The invention discloses a method for synthesizing an alkynecompound, which comprises the following steps: allowing a compound in formula (II) and a compound in formula (III) to react in the presence of an inert solvent under the action of catalyst and oxidizing agent to obtain a compound in formula (I). The synthesis method has simple and easily available materials, safe and simple operation, wide application range of substrate and good selectivity, doesn't need pre-activating, and is easily involved in free radical reaction, and byproducts are nitrogen and water, which conforms to sustainable green chemistry. The alkyne compound obtained by the above synthesis method is a brand-new alkyne compound, and the alkyne compound can be widely used in the fields of medicine and materials, and solves the technical problems of high cost, low stability andcomplication of alkyne compound synthesis reaction in the prior art.
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Paragraph 0085-0087
(2018/12/13)
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- Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions
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A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the p
- Ibrahim, Mansur B.,Ali, Bassam El,Malik, Imran,Fettouhi, Mohammed
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p. 554 - 558
(2016/01/20)
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- Synthesis, crystal structures and catalytic activities of new palladium(II)–bis(oxazoline) complexes
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Palladium–bis(oxazoline) complexes (Pd-BOX-A and Pd-BOX-B) were synthesized and characterized by 1H, 13C NMR, IR and elemental analysis. The molecular structures of the complexes were confirmed by single-crystal X-ray analysis. In both cases, the palladium center is coordinated by the nitrogen atoms of the two oxazoline rings and two chloride ligands in a distorted square planar geometry. Despite the fact that the bis(oxazoline) ligand is achiral, the asymmetrical substitution on the phenyl spacer and the rigid backbone of the complex Pd-BOX-A induce inherent chirality and the compound crystallizes as a racemic mixture. Both complexes were found to be highly effective catalysts for Suzuki–Miyaura, Mizoroki–Heck and Sonogashira cross-coupling reactions. They also show excellent catalytic activities toward carbonylative coupling reactions.
- Ibrahim, Mansur B.,Malik, Imran,Shakil Hussain,Fazal, Atif,Fettouhi, Mohammed,El Ali, Bassam
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p. 739 - 749
(2016/09/13)
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- Copper-catalyzed aerobic oxidative transformation of ketone- Derived N-tosyl hydrazones: An entry to alkynes
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A novel strategy involving Cu-catalyzed oxidative transformation of ketone-derived hydrazone moiety to various synthetic valuable internal alkynes and diynes has been developed. This method features inexpensive metal catalyst, green oxidant, good functional group tolerance, high regioselectivity and readily available starting materials. Oxidative deprotonation reactions were carried out to form internal alkynes and symmetrical diynes. Cross-coupling reactions of hydrazones with halides and terminal alkynes were performed to afford functionalized alkynes and unsymmetrical conjugated diynes. A mechanism proceeding through a Cu-carbene intermediate is proposed for the CC triple bond formation.
- Li, Xianwei,Liu, Xiaohang,Chen, Huoji,Wu, Wanqing,Qi, Chaorong,Jiang, Huanfeng
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p. 14485 - 14489
(2015/02/05)
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- Suzuki, Heck, and copper-free Sonogashira reactions catalyzed by 4-amino-5-methyl-3-thio-1,2,4-triazole-functionalized polystyrene resin-supported Pd(II) under aerobic conditions in water
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4-amino-5-methyl-3-thio-1,2,4-triazole-functionalized polystyrene resin-supported Pd(II) complex was found to be an efficient catalyst in the palladium-catalyzed Suzuki-Miyaura coupling reactions of aryliodides and bromides, Mizoroki-Heck reactions of aryliodides and bromides, and copper-free Sonogashira reactions of aryliodides and bromides in water. Under appropriate conditions, all of these reactions give the desired products in moderate to excellent yields. The catalyst is air-stable and easily available. The palladium catalyst is easily separated, and can be reused for several times without a significant loss in its catalytic activity.
- Bakherad, Mohammad,Keivanloo, Ali,Bahramian, Bahram,Jajarmi, Saeideh
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p. 206 - 212
(2013/03/13)
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- Synthesis and characterization of novel chiral NHC-palladium complexes and their application in copper-free Sonogashira reactions
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A new series of chiral N-heterocyclic carbene (NHC) palladium complexes were synthesized from a relatively inexpensive amino acid, l-phenylalanine. All these compounds were fully characterized by 1H-NMR, 13C-NMR and elemental analysis. The X-ray molecular structures of two of the complexes were reported. The catalytic activity of the four palladium complexes was successfully tested in the Sonogashira reaction under copper free conditions in air. The palladium complex 3a provided good activity in the Sonogashira coupling reaction. The Royal Society of Chemistry 2012.
- Yang, Longguang,Guan, Pei,He, Pan,Chen, Qian,Cao, Changsheng,Peng, Yu,Shi, Zhan,Pang, Guangsheng,Shi, Yanhui
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experimental part
p. 5020 - 5025
(2012/06/04)
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- Cross-coupling of nonactivated alkyl halides with alkynyl grignard reagents: A nickel pincer complex as the catalyst
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In a pinch: The nickel pincer complex 1 catalyzes the cross-coupling of the title compounds with remarkable substrate scope and functional group tolerance. A nickel/alkynyl species was isolated and shown to be catalytically competent. THF=tetrahydrofuran, O-TMEDA=bis[2-(N,N-dimethylaminoethyl)] ether. Copyright
- Vechorkin, Oleg,Godinat, Aurélien,Scopelliti, Rosario,Hu, Xile
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p. 11777 - 11781
(2012/01/19)
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- Palladium-catalyzed Sonogashira coupling of aryl mesylates and tosylates
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Up to speed: The first general and mild protocol for the Sonogashira coupling of aryl mesylates is presented (see scheme). The coupling intermediate also provides facile access to 2-substituted isoquinolines.
- Choy, Pui Ying,Chow, Wing Kin,So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 9982 - 9985
(2010/11/16)
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- Microwave enhanced cross-coupling reactions involving alkenyl- and alkynyltrifluoroborates
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Cross-coupling reactions of potassium alkenyltrifluoroborates and alkynyltrifluoroborates with aryl triflates in the presence of a palladium catalyst occur rapidly utilizing microwave irradiation. The coupled products are generated in good to excellent yi
- Kabalka, George W.,Naravane, Abhijit,Zhao, Li Li
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p. 7091 - 7093
(2008/03/11)
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- Copper-free sonogashira coupling reaction with PdCl2 in water under aerobic conditions
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(Chemical Equation Presented). A mild protocol for the copper-free Sonogashira coupling of aryl iodides with terminal acetylenes in water under aerobic conditions has been developed. The use of 1 mol % PdCl2 in the presence of pyrrolidine allows the coupling reaction to proceed at room temperature or 50°C with good to excellent yields.
- Liang, Bo,Dai, Mingji,Chen, Jiahua,Yang, Zhen
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p. 391 - 393
(2007/10/03)
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- Sonogashira coupling of aryl halides catalyzed by palladium on charcoal
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With the proper choice of solvent, palladium on charcoal acts as an efficient catalyst in the Sonogashira cross-coupling reaction of aryl bromides. The catalytically active species in the process is probably palladium, which leaches into the solution but
- Novak, Zoltan,Szabo, Andras,Repasi, Jozsef,Kotschy, Andras
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p. 3327 - 3329
(2007/10/03)
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- Development of the Suzuki-Miyaura cross-coupling reaction: Use of air-stable potassium alkynyltrifluoroborates in aryl alkynylations
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The palladium-catalyzed cross-coupling reaction of potassium alkynyltrifluoroborates with aryl halides or triflates proceeds readily with moderate to excellent yields. The potassium alkynyltrifluoroborates are air- and moisture-stable crystalline solids t
- Molander, Gary A.,Katona, Bryson W.,Machrouhi, Fouzia
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p. 8416 - 8423
(2007/10/03)
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