- Halogen-Bridged Methylnaphthyl Palladium Dimers as Versatile Catalyst Precursors in Coupling Reactions
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Halogen-bridged methylnaphthyl (MeNAP) palladium dimers are presented as multipurpose Pd-precursors, ideally suited for catalytic method development and preparative organic synthesis. By simply mixing with phosphine or carbene ligands, they are in situ converted into well-defined monoligated complexes. Their catalytic performance was benchmarked against state-of-the-art systems in challenging Buchwald–Hartwig, Heck, Suzuki and Negishi couplings, and ketone arylations. Their use enabled record-setting activities, beyond those achievable by optimization of the ligand alone. The MeNAP catalysts permit syntheses of tetra-ortho-substituted arenes and bulky anilines in near-quantitative yields at room temperature, allow mono-arylations of small ketones, and enable so far elusive cross-couplings of secondary alkyl boronic acids with aryl chlorides.
- Doppiu, Angelino,Goo?en, Lukas J.,Hu, Zhiyong,Pirkl, Nico,Sivendran, Nardana
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supporting information
p. 25151 - 25160
(2021/10/19)
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- Dehydrogenative Formation of Resorcinol Derivatives Using Pd/C-Ethylene Catalytic System
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The conversion of substituted 1,3-cyclohexanediones to the alkyl ethers of resorcinol using a Pd/C-ethylene system is reported. In these reactions, ethylene works as a hydrogen acceptor. The efficient synthesis of resveratrol was achieved using this protocol as a key step. In addition, the direct formation of substituted resorcinols was carried out by adding K2CO3 into the reaction media.
- El-Deeb, Ibrahim Yussif,Funakoshi, Tatsuya,Shimomoto, Yuya,Matsubara, Ryosuke,Hayashi, Masahiko
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p. 2630 - 2640
(2017/03/14)
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- Chromanol derivatives - A novel class of CETP inhibitors
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Based on our former development candidate BAY 38-1315, optimization efforts led to the discovery of a novel chemical class of orally active cholesteryl ester transfer protein (CETP) inhibitors. The chromanol derivative 19b is a highly potent CETP inhibitor with favorable pharmacokinetic properties suitable for clinical studies. Chemical process optimization furnished a robust synthesis for a kilogram-scale process.
- Vakalopoulos, Alexandros,Schmeck, Carsten,Thutewohl, Michael,Li, Volkhart,Bischoff, Hilmar,Lustig, Klemens,Weber, Olaf,Paulsen, Holger,Elias, Harry
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scheme or table
p. 488 - 491
(2011/02/27)
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- An expedient synthesis of isopropyl anisoles and veratroles
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Isopropyl-substituted anisoles and veratroles were obtained in high yields (89-93%) on the aqueous work-up of the reaction of 3-(methoxyphenyl)-2-oxopropanoic acids with iodomethane and potassium hydroxide in dimethyl sulfoxide.
- Yli-Kauhaluoma, Jari T.,Janda, Kim D.
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p. 4509 - 4510
(2007/10/02)
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- SYNTHESIS OF A CARBOCYCLIC ANALOG OF QUERCETIN VIA A BARBIER REACTION
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A six-step synthetic route to the carbocyclic flavonoid 2 is described.The key step involves a 1,4-addition of a tertiary bromide to a α,β-unsaturated ester by the Barbier reaction.
- Shih, Neng-Yang,Mangiaracina, Pietro,Green, Michael J.,Ganguly, Ashit K.
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p. 5563 - 5566
(2007/10/02)
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- STEREOCHEMISTRY OF PHOTOSOLVOLYSIS OF A CHIRAL, 18O-LABELED 1-ARYLETHYL ACETATE
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The stereochemistry of photosolvolysis of (R)-(+)-1-(3,5-dimethoxyphenyl)ethyl acetate-ether-18O in methanol-water and 2,2,2-trifluoroethanol has been determined.An ion pair intermediate was detected in the latter solvent.
- Jaeger, David A.,Angelos, George H.
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p. 803 - 806
(2007/10/02)
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