- Absolute rate constants of alkene addition reactions of a fluorinated radical in water
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Absolute rate constants of ·RfSO3-radical addition to a series of water-soluble alkenes containing ionic, carboxylate substituents were measured by laser flash photolysis experiments in water. The observed rate constants w
- Zhang,Dolbier Jr.,Sheeller,Ingold
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- Heteroatom Donor-Decorated Polymer-Immobilized Ionic Liquid Stabilized Palladium Nanoparticles: Efficient Catalysts for Room-Temperature Suzuki-Miyaura Cross-Coupling in Aqueous Media
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Palladium nanoparticles stabilized by heteroatom donor-modified polystyrene-based polymer immobilized ionic liquids (PdNP@HAD-PIILP; HAD-PPh2, OMe, NH2, CN, pyrrolidone) are highly efficient catalysts for the Suzuki-Miyaura cross-cou
- Doherty, Simon,Knight, Julian G.,Backhouse, Tom,Abood, Einas,Al-shaikh, Hind,Clemmet, Ashley R.,Ellison, Jack R.,Bourne, Richard A.,Chamberlain, Thomas W.,Stones, Rebecca,Warren, Nicholas J.,Fairlamb, Ian J. S.,Lovelock, Kevin R. J.
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- Pd-Catalyzed Synthesis of Vinyl Arenes from Aryl Halides and Acrylic Acid
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Acrylic acid is presented as an inexpensive, non-volatile vinylating agent in a palladium-catalyzed decarboxylative vinylation of aryl halides. The reaction proceeds through a Heck reaction of acrylic acid, immediately followed by protodecarboxylation of the cinnamic acid intermediate. The use of the carboxylate group as a deciduous directing group ensures high selectivity for monoarylated products. The vinylation process is generally applicable to diversely substituted substrates. Its utility is shown by the synthesis of drug-like molecules and the gram-scale preparation of key intermediates in drug synthesis.
- Gao, Yang,Ou, Yang,Goo?en, Lukas J.
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supporting information
p. 8709 - 8712
(2019/06/17)
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- D-A-D type dinitriles with vapor-dependent luminescence in the solid state
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D-A-D (Donor-Acceptor-Donor) type dinitriles linked by a styryl or phenylethynyl group have been prepared. These groups were introduced to increase the flexibility and the size of the π-conjugation in the chromophores. Both compounds showed strong emission in the solid state, AIE (aggregation-induced emission) behavior, and mechanochromism. The fluorescence color of ground powder changed by organic solvent vapor (vapochromism). Especially, the emission color of the styryl dinitrile after exposures depends on the solvent, while that of the phenylethynyl dinitrile is the same after exposure to different solvents. These results were explained by single crystal and powder XRD measurements, which revealed that the flexible styryl linker leads to a loose crystal packing, resulting in a dinitrile with multi-state microcrystalline structures. This methodology based on the flexible linker allows for the detection of small organic molecules without transition metals.
- Furuyama, Taniyuki,Shinozaki, Junichi,Tasso, Thiago Teixeira,Maeda, Hajime,Segi, Masahito,Kobayashi, Nagao
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supporting information
p. 4243 - 4247
(2017/10/12)
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- Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids
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Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.
- Wu, Guojiao,Deng, Yifan,Wu, Chaoqiang,Zhang, Yan,Wang, Jianbo
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supporting information
p. 10510 - 10514
(2016/02/18)
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- Intermolecular aminotrifluoromethylation of alkenes by visible-light-driven photoredox catalysis
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Intermolecular aminotrifluoromethylation of alkenes catalyzed by [Ru(bpy)3]2+ under visible light irradiation has been explored. The present photocatalytic protocol achieves highly efficient and regioselective difunctionalization of C=C bonds, leading to a variety of β-trifluoromethylamines. The reaction is applied to late-stage aminotrifluoromethylation of steroid and amino acid scaffolds.
- Yasu, Yusuke,Koike, Takashi,Akita, Munetaka
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supporting information
p. 2136 - 2139
(2013/06/05)
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- Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates
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Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright
- Shang, Rui,Ji, Dong-Sheng,Chu, Ling,Fu, Yao,Liu, Lei
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supporting information; experimental part
p. 4470 - 4474
(2011/06/24)
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- Optimization of polystyrene-supported triphenylphosphine catalysts for aza-Morita-Baylis-Hillman reactions
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A series of polar group functionalized polystyrene-supported phosphine reagents were examined as catalysts in the aza-Morita-Baylis-Hillman reactions of N-tosyl arylimines and a variety of Michael acceptors with the aim of identifying the optimal polymer/solvent combination. For these reactions JandaJel-PPh3 (1 mmol PPh3/g loading) resin containing methoxy groups (JJ-OMe-PPh3) on the polystyrene backbone in THF solvent provided the highest yield of all the catalyst/solvent combinations examined. The methyl ether groups were incorporated into JJ-OMe-PPh3 using commercially available 4-methoxystyrene, and thus such polar polystyrene resins are easily accessible and should find utility as nucleophilic catalyst supports.
- Zhao, Lin-Jing,Kwong, Cathy Kar-Wing,Shi, Min,Toy, Patrick H.
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p. 12026 - 12032
(2007/10/03)
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