- Electrochemical [4+2] Annulation-Rearrangement-Aromatization of Styrenes: Synthesis of Naphthalene Derivatives
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We report the first electrochemical strategy to synthesize functionalized naphthalene derivatives through [4+2] annulation—rearrangement–aromatization from styrenes under mild conditions. The electrolysis does not require metals, oxidants and high valence substrates, indicating the atom and step-economy ideals. The dehydrodimer produced through [4+2] cycloaddition of 4-methoxy α-methyl styrene is isolated and proved to be the key intermediate for the following oxydehydrogenation to form carbon cation, which undergoes rearrangement–aromatization to afford the final products. This reaction represents a powerful access to construct multi-substituted naphthalene blocks in a single step.
- Ma, Yueyue,Lv, Jufeng,Liu, Chengyu,Yao, Xiantong,Yan, Guoming,Yu, Wei,Ye, Jinxing
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p. 6756 - 6760
(2019/04/17)
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- Extending the substrate scope of bicyclic p-oxazoline/thiazole ligands for ir-catalyzed hydrogenation of unfunctionalized olefins by introducing a biaryl phosphoroamidite group
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This study identifies a series of Ir-bicyclic phosphoroamidite-oxazoline/thiazole catalytic systems that can hydrogenate a wide range of minimally functionalized olefins (including E- and Z-tri- and disubstituted substrates, vinylsilanes, enol phosphinates, tri- and disubstituted alkenylboronic esters, and ?±,?2-unsaturated enones) in high enantioselectivities (ee values up to 99%) and conversions. The design of the new phosphoroamidite-oxazoline/thiazole ligands derives from a previous successful generation of bicyclic N-phosphane-oxazoline/thiazole ligands, by replacing the N-phosphane group with a p-acceptor biaryl phosphoroamidite moiety. A small but structurally important family of Ir-phosphoroamidite-oxazoline/thiazole precatalysts has thus been synthesized by changing the nature of the Ndonor group (either oxazoline or thiazole) and the configuration at the biaryl phosphoroamidite moiety. The substitution of the N-phosphane by a phosphoroamidite group in the bicyclic N-phosphane-oxazoline/thiazole ligands extended the range of olefins that can be successfully hydrogenated.
- Biosca, Maria,Paptchikhine, Alexander,P??mies, Oscar,Andersson, Pher G.,Di??guez, Montserrat
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p. 3455 - 3464
(2015/03/04)
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- Studies on the 1,2-migrations in Pd-catalyzed negishi couplings with JosiPhos ligands
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(Chemical Equation Presented) We report an initial investigation with the goal of determining the factors that control the 1,2-migration in the Negishi cross-coupling, which is promoted by palladium catalyst systems generated with JosiPhos ligands. Severa
- Lindhardt, Anders T.,G?gsig, Thomas M.,Skrydstrup, Troels
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supporting information; experimental part
p. 135 - 143
(2009/04/07)
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- Substituent effects on the solvolysis rates and gas phase stabilities of 1,2,2-trimethyl-1-phenylpropyl and 1,2,2-trimethyl-1-(2-methylphenyl)propyl systems
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Substituent effects on the solvolysis rates of 1,2,2-trimethyl-1- phenylpropyl chlorides in 80% (v/v) aq acetone at 45 °C and 1,2,2-trimethyl- 1-(2-methylphenyl)propyl p-nitrobenzoates in 50% (v/v) aq ethanol at 75 °C were correlated with the Yukawa-Tsuno
- Nakata, Kazuhide,Fujio, Mizue,Mishima, Masaaki,Nomura, Hideyuki,Tsuno, Yuho,Nishimoto, Kichisuke
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p. 581 - 590
(2007/10/03)
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