- Pd(DIPHOS)2-catalyzed cross-coupling reactions of organoborons with free or polymer-bound aryl halides.
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Bis[1,2-bis(diphenylphosphino)ethane]palladium(0) [Pd(DIPHOS)2] catalyzes cross-coupling reactions of free or polymer-bound aryl halides with organoboron compounds to produce biaryls in overall yields of 60-96%.
- De,Krogstad
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Read Online
- Copper-mediated formal [5+1] annulation of 2-vinylanilines and glyoxylic acid: A facile approach for the synthesis of 4-arylated quinolines
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A copper-mediated formal [5 + 1] oxidative annulation of 2-vinylanilines and glyoxylic acid to 4-arylated quinolines was developed. A series of 4-arylated quinoline derivatives were obtained in good to excellent yields. This protocol could be carried out efficiently on gram scale. The transformation probably underwent nucleophilic addition/6π electrocyclization/oxidative aromatization and the elimination of CO2 cascade processes.
- Xiang, Yunyu,Luo, Puying,Hao, Tianxin,Xiong, Weikang,Song, Xiaolin,Ding, Qiuping
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- 3,3'-((Arylmethylene)bis(4-methoxy-3,1-phenylene)) dipyridine derivatives as convenient ligands for Suzuki–Miyaura chemo- and homoselective cross-coupling reactions
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Four novel N,N-bidentate triarylmethane-based ligands bearing β-pyridyl residues have been prepared and the catalytic activity of their in-situ generated palladium complexes were studied in the Suzuki–Miyaura cross-coupling reactions. Air and moisture stable 3,3'-((arylmethylene)bis(4-methoxy-3,1-phenylene))dipyridines L1-3 showed excellent activity in the Suzuki coupling reactions of aryl halides with aryl boronic acids under thermal and sonochemical reaction conditions. The described methodology provided good to high yields in short reaction times at ambient conditions. Moreover, it offered a straightforward way for Suzuki–Miyaura chemo- and homoselective cross-coupling of aryl halides with phenyl boronic acid. The structures of synthesized compounds were fully characterized by FT-IR, 1H-NMR, 13C-NMR, and elemental analyses. The coordination of palladium acetate to nitrogen sites of L1 was also studied using FTIR spectroscopy, EDX analysis and SEM observations. Graphic abstract: The in-situ generated Pd-complexes of N,N-bidentate ligands L1-3 are described as robust and highly effective catalytic systems for the Suzuki cross-coupling of aryl halides with aryl boronic acids under thermal and sonochemical reaction conditions.[Figure not available: see fulltext.]
- Hosseini, Raziyeh,Mohammadiannejad, Kazem,Ranjbar-Karimi, Reza
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- Microwave-Assisted Metal-Free Rapid Synthesis of C4-Arylated Quinolines via Povarov Type Multicomponent Reaction
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A rapid microwave assisted, (±) camphor-10-sulfonic acid (CSA) promoted, Povarov type multicomponent synthesis of 4-arylated quinolines from anilines, alkynes, and paraformaldehyde is described. This reaction proceeds through [4+2] cycloaddition of imine (formed in situ from aniline and paraformaldehyde) and alkynes in the presence of CSA, without any metal catalyst. Mechanistic study revealed that CSA inhibit the synthesis of Troger's base and assist the cycloaddition of imines with alkynes by activating the imine.
- Chandra, Devesh,Dhiman, Ankit Kumar,Kumar, Rakesh,Sharma, Upendra
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p. 2753 - 2758
(2019/04/08)
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- Direct Synthesis of Quinolines via Co(III)-Catalyzed and DMSO-Involved C-H Activation/Cyclization of Anilines with Alkynes
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A unique Co(III)-catalyzed and DMSO-involved C-H activation/cyclization of simple, cheap, and easily available anilines with alkynes for direct and highly efficient synthesis of privileged quinolines with exclusive regioselectivity and broad substrate/functional group tolerance and in good to excellent yields, where DMSO was employed as both the solvent and the C1 building block of quinoline products, is reported. Mechanistic experiments revealed that the versatile reaction might employ the 2-vinylbenzenamine species as the active intermediate.
- Xu, Xuefeng,Yang, Yurong,Zhang, Xu,Yi, Wei
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supporting information
p. 566 - 569
(2018/02/10)
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- The one-pot synthesis of quinolines: Via Co(iii)-catalyzed C-H activation/carbonylation/cyclization of anilines
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We herein disclose a novel Co(iii)-catalyzed C-H activation/carbonylation/cyclization of anilines with ketones using paraformaldehyde as the carbonyl source, giving direct access to diverse quinolines with broad functional group tolerance and in good to excellent yields. Moreover, exclusive site-/region-selectivity was observed in this versatile transformation.
- Xu, Xuefeng,Yang, Yurong,Chen, Xin,Zhang, Xu,Yi, Wei
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supporting information
p. 9061 - 9065
(2017/11/14)
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- Copper-Catalyzed Coupling of Triaryl- and Trialkylindium Reagents with Aryl Iodides and Bromides through Consecutive Transmetalations
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An efficient copper(I)-catalyzed coupling of triaryl and trialkylindium reagents with aryl iodides and bromides is reported. The reaction proceeds at low catalyst loadings (2 mol %) and generally only requires 0.33 equivalents of the triorganoindium reagent with respect to the aryl halide as all three organic nucleophilic moieties of the reagent are transferred to the products through consecutive transmetalations. The reaction tolerates a variety of functional groups and sterically hindered substrates. Furthermore, preliminary mechanistic studies that entailed the synthesis and characterization of potential reaction intermediates offered a glimpse of the elementary steps that constitute the catalytic cycle.
- Thapa, Surendra,Gurung, Santosh K.,Dickie, Diane A.,Giri, Ramesh
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supporting information
p. 11620 - 11624
(2016/02/19)
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- Ligand-Free Copper-Catalyzed Negishi Coupling of Alkyl-, Aryl-, and Alkynylzinc Reagents with Heteroaryl Iodides
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Reported herein is an unprecedented ligand-free copper-catalyzed cross-coupling of alkyl-, aryl-, and alkynylzinc reagents with heteroaryl iodides. The reaction proceeds at room temperature for the coupling of primary, secondary, and tertiary alkylzinc reagents with heteroaryl iodides without rearrangement. An elevated temperature (100 C) is required for aryl-heteroaryl and alkynyl-heteroaryl couplings.
- Thapa, Surendra,Kafle, Arjun,Gurung, Santosh K.,Montoya, Adam,Riedel, Patrick,Giri, Ramesh
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p. 8236 - 8240
(2015/07/07)
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- Novel pharmaceutical compounds
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The instant invention provides compounds of Formula I which are leukotriene biosynthesis inhibitors. Compounds of Formula I are useful as anti-atherosclerotic, anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.
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Page/Page column 44
(2008/12/07)
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- A manganese-catalyzed cross-coupling reaction
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A manganese-catalyzed cross-coupling reaction of heterocyclic chlorides with aryl- as well as alkylmagnesium halides has been developed. The reaction provides a variety of heterocyclic compounds under mild and practical reaction conditions using low amounts of manganese chloride as catalyst. Georg Thieme Verlag Stuttgart.
- Rueping, Magnus,Ieawsuwan, Winai
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p. 247 - 250
(2007/10/03)
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- SUBSTITUTED QUINOLINES AS INHIBITORS OF LEUKOTRIENE BIOSYNTHESIS
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The instant invention provides compounds of Formula (I) which are leukotriene biosynthesis inhibitors. Compounds of Formula (I) are useful as anti-atherosclerotic, anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.
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Page/Page column 37
(2008/06/13)
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- Palladium-catalyzed Suzuki-Miyaura cross-coupling using phosphinous acids and dialkyl(chloro)phosphane ligands
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The use of eleven palladium complexes having monomeric and μ-chloro-bridged dimeric structures and either bulky dialkyl- and diarylphosphinous acid ligands (POPd, POPd-Br, POPd1, POPd2, POPd6, POPd7, Ph1-Phoxide) or dialkyl(chloro)phosphane ligands (PXPd, PXPd2, PXPd6, PXPd7) for Suzuki-Miyaura coupling reactions has been evaluated. Screening and optimization of catalyst loading, solvent, temperature, and base showed that excellent results can be obtained with electron-deficient and electron-rich aryl iodides, bromides, and chlorides in the presence of 2.5 mol-% of palladium-phosphinous acid POPd, (tBu2POH)2PdCl2, in 1,4-dioxane using cesium carbonate as base. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Wolf, Christian,Ekoue-Kovi, Kekeli
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p. 1917 - 1925
(2007/10/03)
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- Comparison of the Suzuki cross-coupling reactions of 4,7-dichloroquinoline and 7-chloro-4-iodoquinoline with arylboronic acids using phosphine-free palladium catalysis in water
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4,7-Dichloroquinoline (1a) and 7-chloro-4-iodoquinoline (1b) undergo Suzuki cross-coupling reactions with arylboronic acids catalyzed by phosphine-free palladium acetate in boiling water. Using phenylboronic acid (2), the reaction of 1a provides 7-chloro-4-phenylquinoline (3) (78%) together with diphenylquinoline (4) (12%), while 1b reacts in a much more regioselective fashion and provides 3 in 98% isolated yield. Although 1b undergoes a more regio-selective Suzuki reaction than 1a, additional important observations are that the overall reaction of 1b with 2 is three times slower than 1a and that the reaction occurs in the absence of tetrabutylammonium bromide. Using optimized reaction conditions, a variety of aryl and vinylboronic acids undergo regioselective Suzuki cross-coupling with 1b to provide the products 7, 10, and 11 in good to excellent yield.
- Friesen, Richard W.,Trimble, Laird A.
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p. 206 - 214
(2007/10/03)
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- Efficient Stille cross-coupling reaction using aryl chlorides or bromides in water
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An efficient Stille cross-coupling reaction using a variety of aryl halides in neat water has been developed. Employing palladium-phosphinous acid catalyst [(t-Bu)2P(OH)]2PdCl2 allows formation of biaryls from aryl chlorides and bromides in good to high yields. Functional groups such as ketones and nitriles are tolerated, and organic cosolvents are not required. The air stability and solubility in water of the palladium complexes used in this study facilitate operation of the coupling reaction and product isolation. The feasibility of catalyst recycling has also been demonstrated.
- Wolf, Christian,Lerebours, Rachel
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p. 7551 - 7554
(2007/10/03)
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- Direct Synthesis of Benzoylpyridines from Chloropyridines via a Palladium-Carbene Catalyzed Carbonylative Suzuki Cross-Coupling Reaction
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The use of N-heterocyclic carbene-type ligands with palladium catalysts allows the activation of chloropyridines and chloroquinoline towards carbonylative cross-coupling with phenylboronic acid for the synthesis of unsymmetrical biaryl ketones.
- Maerten, Eddy,Hassouna, Fatima,Couve-Bonnaire, Samuel,Mortreux, André,Carpentier, Jean-Fran?ois,Castanet, Yves
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p. 1874 - 1876
(2007/10/03)
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- Cross-coupling reactions of aryl chlorides and bromides with phenyltrimthoxysilane catalyzed by palladium-phosphinous acid complexes
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Three palladium-phosphinous acid complexes, POPd, POPd1, and POPd2, have been employed in cross-coupling reactions of aryl halides and phenyltrimethoxysilane activated by tetrabutylammonium fluoride. A variety of biaryls were prepared from aryl and hetaryl chlorides and bromides in good to high yields under mild reaction conditions. Bromides afford better results than their chloride analogs and acetonitrile was found to be a superior solvent over DMF, ethyl acetate, and isopropyl alcohol. This coupling procedure tolerates nitrile, ketone and ester groups and converts 4,7-dichloroquinoline to 7-chloro-4-phenylquinoline with high regioselectivity.
- Wolf, Christian,Lerebours, Rachel,Tanzini, Elizabeth H.
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p. 2069 - 2073
(2007/10/03)
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- Palladium-catalysed cross-coupling reactions of arylboronic acids with π-deficient heteroaryl chlorides
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The palladium-catalysed cross-coupling reactions of arylboronic acids with a variety of π-deficient heteroaryl chlorides proceed in high yield. [1,4-Bis(diphenylphosphino)butane]palladium(II) dichloride was found to be a very satisfactory catalyst for monocyclic heteroaryl chlorides, whereas tetrakis(triphenylphosphine)palladium(O) was found to be excellent for a range of chloroquinoline derivatives.
- Ali,McKillop,Mitchell,Rebelo,Wallbank
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p. 8117 - 8126
(2007/10/02)
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