- Metal-Organic Layers Catalyze Photoreactions without Pore Size and Diffusion Limitations
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Metal-organic frameworks (MOFs) have emerged as promising single-site solid catalysts for organic reactions. However, MOF catalysts suffer from pore size limitation and slow diffusion, which are detrimental for photoreactions. Metal-organic layers (MOLs)
- Xu, Ruoyu,Drake, Tasha,Lan, Guangxu,Lin, Wenbin
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supporting information
p. 15772 - 15776
(2018/10/02)
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- γ-Amino Butyric Acid (GABA) Synthesis Enabled by Copper-Catalyzed Carboamination of Alkenes
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γ-Amino butyric acid (GABA) is the chief inhibitory neurotransmitter in the mammalian central nervous system. Many GABA derivatives are used clinically to prevent or treat neurodegenerative diseases. Copper-catalyzed carboamination of alkenes offers an efficient method to fashion the core structure of GABA derivatives from alkenes. In this reaction, acetonitrile serves as the source of the carbon and nitrogen functionalities used to difunctionalize alkenes. Experimental and density functional theory (DFT) studies were carried out to investigate the mechanism of the reaction, and a copper-catalyzed radical-polar crossover mechanism is proposed.
- Zhu, Nengbo,Wang, Ting,Ge, Liang,Li, Yajun,Zhang, Xinhao,Bao, Hongli
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supporting information
p. 4718 - 4721
(2017/09/23)
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- The photoredox-catalyzed meerwein addition reaction: Intermolecular amino-arylation of alkenes
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A variety of amides are efficiently accessible under mild conditions by intermolecular amino-arylation using a photo Meerwein addition with visible light. The reaction has a broad substrate scope, tolerates a large range of functional groups, and was applied to the synthesis of a 3-aryl-3,4- dihydroisoquinoline. From elimination to addition: A variety of amides are efficiently accessible under mild conditions by intermolecular amino-arylation using a photo Meerwein addition with visible light. The reaction has a broad substrate scope, tolerates a large range of functional groups, and was applied to the synthesis of 3-aryl-3,4-dihydroisoquinoline. Copyright
- Prasad Hari, Durga,Hering, Thea,K?nig, Burkhard
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p. 725 - 728
(2014/01/23)
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- Oxyarylation and aminoarylation of styrenes using photoredox catalysis
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A three-component coupling of styrenes is reported, using photoredox catalysis to achieve simultaneous arylation and C-O or C-N bond formation across the styrene double bond.
- Fumagalli, Gabriele,Boyd, Scott,Greaney, Michael F.
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supporting information
p. 4398 - 4401
(2013/09/24)
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- A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines
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A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented.Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3.Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields.The method is also highly effective with (2-phenylethyl)amides.
- Larsen, Robert D.,Reamer, Robert A.,Corley, Edward G.,Davis, Paul,Grabowski, Edward J. J.,et al.
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p. 6034 - 6038
(2007/10/02)
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- Carbon-Hydrogen vs. Carbon-Carbon Bond Cleavage of 1,2-Diarylethane Radical Cations in Acetonitrile-Water
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Radical cations of 1,2-diarylethanes and 1-phenyl-2-arylethanes (Ar = phenyl, p-tolyl, p-anisyl) were generated in acidic 70percent acetonitrile-water by Cu2+-catalyzed peroxydisulfate oxidation.The radical cations fragment mainly by loss of benzylic protons (C-H cleavage) rather than by alkyl C-C bond cleavage.The radical cation of 2,3-dimethyl-2,3-diphenylbutane fragments efficiently by C-C cleavage, forming cumyl radical and cumyl cation.Oxidations of bibenzyl-bicumyl mixtures show selective oxidation of bicumyl dependent on total substrate concentration, providing evidence of equilibrating radical cations and showing that bicumyl fragments faster than bibenzyl loses protons.The effects of reaction conditions and substrate structure on reactivity are discussed.
- Camaioni, Donald M.,Franz, James A.
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p. 1607 - 1613
(2007/10/02)
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- The mechanism of the Bischler-Napieralski Reaction
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The Bischler-Napieralski dihydroisoquinoline synthesis was proven to occur via imidoyl chlorides and the corresponding nitrilium salt.Two-step process required much milder conditions (20 degC - 50 degC) compared to drastic classical conditions of refluxing at 100 degC - 200 degC.The Bischler-Napieralski reaction is shown to share a common intermediate with two other well-known reactions: the von Braun and the Ritter reactions
- Nagubandi, Sreeramulu,Fodor, G.
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p. 1457 - 1463
(2007/10/02)
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- Reversal of the Ritter Reaction as Observed Under Electron Impact Conditions
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Fragmentations of various 2-phenethylamides, trifluoroacylimidates and imidoyl triflouromethyl sulfonates have been studied and a pathway for the formation of retro-Ritter reaction products is proposed.
- Nagubandi, Sreeramulu
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p. 535 - 538
(2007/10/02)
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