- Copper-Catalyzed 8-Aminoquinoline-Directed Oxidative C-H/N-H Coupling for N-Arylation of Sulfoximines
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A copper-catalyzed cross-dehydrogenative C-H/N-H coupling has been devised to access a series of N-arylated sulfoximines in high yield from 8-aminoquinoline-derived benzamides and sulfoximines. The reaction is scalable, and mechanistic studies favor the involvement of an organometallic pathway, where C-H bond cleavage is presumed to be the kinetically relevant step. The utility of sulfoximine-coupled benzamides was displayed through the nickel-catalyzed acceptorless dehydrogenative olefination of benzyl alcohols.
- Grandhi, Gowri Sankar,Dana, Suman,Mandal, Anup,Baidya, Mahiuddin
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supporting information
p. 2606 - 2610
(2020/03/30)
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- Efficient hydroarylation of terminal alkynes with sodium tetraphenylborate performed in water under mild conditions
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The hydroarylation of terminal alkynes with sodium tetraphenylborate was performed in high yield within 3 h at room temperature in water, using palladium(II) complexes with imidazole ligands as catalysts. Under these conditions, differently substituted phenylacetylene substrates were converted to arylalkenes and aryl-substituted dienes. High conversion and excellent selectivity were achieved in the hydroarylation of alkynols with sodium tetraphenylborate. Only one product, arylalkene with an OH group, was formed in these reactions with the yield dependent on the kind of alkynol used. A plausible hydroarylation reaction mechanism was proposed on the basis of the palladium species identified in the reaction mixture and H/D exchange studies. The contribution of water as the hydride source was evidenced.
- Koci?cka,Trzeciak
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- Palladium nanoparticles immobilized on EDTA-modified Fe3O4@SiO2: a highly stable and efficient magnetically recoverable catalyst for the Heck–Mizoroki coupling reactions
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Palladium nanoparticles supported on EDTA-modified Fe3O4@SiO2 NPs as an efficient and magnetically reusable nanocatalyst was applied for the Heck cross-coupling reactions. The catalyst was very effective for the Heck reaction of aryl halides (iodides, bromides, and chlorides) with alkenes and conversion was excellent in most cases with higher TOF (turn over frequency). Moreover, the catalyst could be recycled for eight runs without any significant loss of catalytic activity, showing its superiority over homogeneous catalysts for industrial and chemical applications. Also, the leaching of the catalyst has been examined by a hot filtration test and ICP analysis.
- Esmaeilpour, Mohsen,Zahmatkesh, Saeed
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p. 267 - 276
(2019/09/13)
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- Palladium catalyst supported on PEGylated imidazolium based phosphinite ionic liquid-modified magnetic silica core-shell nanoparticles: A worthy and highly water-dispersible catalyst for organic reactions in water
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A highly water-dispersible palladium nanocatalyst was fabricated by the immobilization of Pd onto the surface of PEGylated imidazolium based phosphinite ionic liquid functionalized γ-Fe2O3@SiO2 core-shell nanoparticles. This nanocatalyst (denoted as [Pd@PEGylated ImIL-OPPh2-γ-Fe2O3@SiO2]) was assessed as a promising Pd catalyst in different organic reactions including Mizoroki-Heck and Sonogashira coupling reactions of aryl halides and the reduction reaction of 4-nitrophenol (4NP) to 4-aminophenol (4AP). From the application point of view, this nanocatalyst showed high thermal versatility, stability, recoverability, and compatibility in aqueous media. The catalyst recovery test revealed that its performance and catalytic activity stayed indefectible during several sequential runs. The loading level of Pd in the [Pd@PEGylated ImIL-OPPh2-γ-Fe2O3@SiO2] catalyst was 0.087 mmol g-1. Pivotal properties including high robustness, efficiency and turnover frequency (TOF), mild reaction conditions, utilization of water as a green solvent, simple product work-up, and facile catalyst recovery make this catalyst favourable from the environmental and economic points of view.
- Bahadorikhalili, Saeed,Ma'mani, Leila,Mahdavi, Hossein,Shafiee, Abbas
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p. 71297 - 71305
(2015/09/08)
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- Magnetically-recoverable Schiff Base Complex of Pd (II) Immobilized on Fe3O4@SiO2 Nanoparticles: An Efficient Catalyst for Mizoroki-Heck and Suzuki-Miyaura Coupling Reactions
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The activity of Pd(II)-Schiff base complexmolecules grafted on the surface of Fe3O4@SiO2 particles were investigated in the palladium-catalyzed coupling reactions of aryl halides with alkenes (Mizoroki-Heck reaction) and phenylboronic acids (Suzuki-Miyaura reaction) in the absence of phosphorous ligands. This method shows notable advantages such as heterogeneous nature of the catalyst, excellent yields, short reaction times, easy preparation, simplicity of operation, and cleaner reaction profiles. The catalyst can be separated from the reaction mixture by applying a permanent magnet externally and can be reused for several times without significant loss of activity. Also, the amount of palladium leaching has been determined by ICP analysis.
- Esmaeilpour, Mohsen,Javidi, Jaber
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p. 614 - 626
(2018/01/18)
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- Pd(II) complexes with mono- and bis-chelate carbene ligands tagged with pyridinium cation: Synthesis, structures, and their catalytic activities toward Heck reaction
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Homoleptic Pd(II) complexes with one and two chelating di-N-heterocyclic carbene (NHC) ligands tagged with pyridinium cation, [Pd2( PyBuCCme)2Cl2](PF6) 6 and [Pd (PyBu
- Lee, Chen-Shiang,Lai, Yong-Bin,Lin, Wan-Jung,Zhuang, Rui Rui,Hwang, Wen-Shu
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p. 235 - 243
(2013/03/13)
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- Nanocrystalline magnesium oxide-stabilized palladium(0): The Heck reaction of heteroaryl bromides in the absence of additional ligands and base
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An efficient and user-friendly protocol has been realized for the Heck reaction of heteroaryl bromides by using a reusable nanocrystalline magnesium oxide-stabilized palladium(0) catalyst without the aid of additional ligands and base. Dimethylamine generated under in situ conditions by the decomposition of DMF serves as the base in this reaction. The catalyst was reused with consistent activity up to four cycles.
- Kantam, Mannepalli Lakshmi,Redddy, Police Vishnuvardhan,Srinivas, Pottabathula,Venugopal, Akula,Bhargava, Suresh,Nishina, Yuta
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p. 2550 - 2554
(2013/09/24)
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- Highly active [Pd(μ-Cl)Cl(NHC)]2 complexes in the Mizoroki-Heck reaction
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A series of Pd dimers bearing an N-heterocyclic carbene ligand was studied in the Mizoroki-Heck reaction. [Pd(μ-Cl)Cl(SIPr)]2 (SIPr = {N,N′-bis[2,6-(diisopropyl)phenyl]imidazolidin-2-ylidene}) was shown to be highly efficient in this cross-coup
- Tessin, Ulrike I.,Bantreil, Xavier,Songis, Olivier,Cazin, Catherine S. J.
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p. 2007 - 2010
(2013/05/21)
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- Ligand and base-free Heck reaction with heteroaryl halides
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Pd(CH3CN)2Cl2-catalyzed Heck reaction of different heteroaryl halides with olefins is carried out in the absence of both the ligand and base to obtain the corresponding coupling products in good yields.
- Lakshmi Kantam,Vishnuvardhan Reddy,Srinivas,Bhargava, Suresh
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supporting information; experimental part
p. 4490 - 4493
(2011/09/19)
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- Enhancement in the catalytic activity of Pd/USY in the Heck reaction induced by H2 bubbling
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Pd was loaded on ultra stable Y (USY) zeolites prepared by steaming NH 4-Y zeolite under different conditions. Heck reactions were carried out over the prepared Pd/USY. We found that H2 bubbling was effective in improving not only the catalytic activity of Pd/USY, but also that of other supported Pd catalysts and Pd(OAc)2. Moreover, the catalytic activity of Pd/USY could be optimized by choosing appropriate steaming conditions for the preparation of the USY zeolites; Pd loaded on USY prepared at 873 K with 100% H2O gave the highest activity (TOF = 61,000 h-1), which was higher than that of Pd loaded on other kinds of supports. The prepared Pd/USY catalysts were applicable to the Heck reactions using various kinds of substrates including bromo-and chlorosubstituted aromatic and heteroaromatic compounds. Characterization of the acid properties of the USY zeolites revealed that the strong acid site (OHstrong) generated as a result of steaming had a profound effect on the catalytic activity of Pd.
- Okumura, Kazu,Tomiyama, Takuya,Moriyama, Sayaka,Nakamichi, Ayaka,Niwa, Miki
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experimental part
p. 38 - 51
(2011/03/22)
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- Lithium hydroxide as base in the Wittig reaction. A simple method for olefin synthesis
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A mild and practical procedure for the Wittig olefination, promoted by lithium hydroxide and triphenylbenzyl phosphonium bromide, has been set up for the synthesis of stilbenes and styrenes. The experimental conditions allow aromatic, heteroaromatic, unsaturated and saturated aliphatic aldehydes to give final products in good yields.
- Antonioletti,Bonadies,Ciammaichella,Viglianti
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p. 4644 - 4648
(2008/09/20)
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- The Synthesis of Naphthothiophene and All of the Eight Isomers of Monomethylnaphthothiophene
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The synthesis of naphthothiophene and all of the eight monomethylnaphthothiophene isomers is described.
- Tedjamulia, Marvin L.,Stuart, John G.,Tominaga, Yoshinori,Castle, Raymond N.,Lee, Milton L.
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p. 1215 - 1219
(2007/10/02)
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