- Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups
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We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.
- Cook, Adam,MacLean, Haydn,St. Onge, Piers,Newman, Stephen G.
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p. 13337 - 13347
(2021/11/20)
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- A one-pot protocol for the fluorosulfonation and Suzuki coupling of phenols and bromophenols, streamlined access to biaryls and terphenyls
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A one-pot protocol for the fluorosulfation and Suzuki coupling of phenols is described. The tandem reaction proceeds efficiently at room temperature, and various biaryls and biaryl fluorosulfates were obtained in good to excellent yields. Furthermore, biaryl fluorosulfates were utilized as versatile building blocks for the preparation of terphenyls. The Royal Society of Chemistry 2020.
- Hu, Rui,Li, Xinmin,Ren, Changyue,Yuan, Zeli,Zhang, Hang,Zhang, Tingting
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supporting information
p. 4748 - 4753
(2020/08/17)
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- Strongly Chemiluminescent Acridinium Esters under Neutral Conditions: Synthesis, Properties, Determination, and Theoretical Study
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Various novel acridinium ester derivatives having phenyl and biphenyl moieties were synthesized, and their optimal chemiluminescence conditions were investigated. Several strongly chemiluminescent acridinium esters under neutral conditions were found, and then these derivatives were used to detect hydrogen peroxide and glucose. Acridinium esters having strong electron-withdrawing groups such as cyano, methoxycarbonyl, and nitro at the 4-position of the phenyl moiety in phenyl 10-methyl-10λ4-acridine-9-carboxylate trifluoromethanesulfonate salt showed strong chemiluminescence intensities. The chemiluminescence intensity of 3,4-dicyanophenyl 10-methyl-10λ4-acridine-9-carboxylate trifluoromethanesulfonate salt was approximately 100 times stronger than that of phenyl 10-methyl-10λ4-acridine-9-carboxylate trifluoromethanesulfonate salt at pH 7. The linear calibration ranges of hydrogen peroxide and glucose were 0.05-10 mM and 10-2000 μM using 3,4-(dimethoxycarbonyl)phenyl 10-methyl-10λ4-acridine-9-carboxylate trifluoromethanesulfonate salt at pH 7 and pH 7.5, respectively. The proposed chemiluminescence reaction mechanism of acridinium ester via a dioxetanone structure was evaluated via quantum chemical calculation on density functional theory. The proposed mechanism was composed of the nucleophilic addition reaction of hydroperoxide anion, dioxetanone ring formation, and nonadiabatic transition due to spin-orbit coupling around the transition state (TS) to the triplet state (T1) following the decomposition pathway. The TS which appeared in the thermal decomposition would be a rate-determining step for all three processes.
- Nakazono, Manabu,Oshikawa, Yuji,Nakamura, Mizuho,Kubota, Hidehiro,Nanbu, Shinkoh
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p. 2450 - 2461
(2017/03/11)
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- Palladium supported on zinc oxide nanoparticles as efficient heterogeneous catalyst for Suzuki-miyaura and hiyama reactions under normal laboratory conditions
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Nanoscale Pd supported on ZnO was prepared by a facile coprecipitation method. Pd/ZnO Nanoparticles were characterized by using XRD, TEM, SEM, XPS, BET specific surface area measurement, and thermogravimetric analysis. This catalyst was used as novel and excellent heterogeneous catalyst for ligand-free C-C bond-formation particularly in the synthesis of unsymmetrical biaryls by Suzuki-Miyaura and Hiyama cross-coupling reactions under air atmosphere without use of any Ar or N2 flow. The catalyst can be recovered and recycled several times without marked loss of activity.
- Hosseini-Sarvari, Mona,Razmi, Zahra
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p. 805 - 818
(2015/06/25)
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- Direct benzylic alkylation via Ni-catalyzed selective benzylic sp 3 C-O activation
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This article demonstrates the first cross coupling of benzyl ether with Grignard reagents via Ni-catalyzed benzylic sp3 C-O activation with high efficiency and excellent chemoselectivity. Benzylic sp3 C-O and aryl sp2 C-O were differentiated, controlled by ligands. Copyright
- Guan, Bing-Tao,Xiang, Shi-Kai,Wang, Bi-Qin,Sun, Zuo-Peng,Wang, Yang,Zhao, Ke-Qing,Shi, Zhang-Jie
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p. 3268 - 3269
(2008/10/09)
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- Design, synthesis, and evaluation of 2-alkoxydihydrocinnamates as PPAR agonists
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A series of 2-alkoxydihydrocinnamates were synthesized as PPARγ and PPARα dual agonists. In vitro studies in cell model showed that these compounds were efficacious. Compound 1g was found to be a potent PPARα/γ dual agonist and will be further evaluated for the treatment of type II diabetes.
- Lu, Ying,Guo, Zongru,Guo, Yanshen,Feng, Jun,Chu, Fengming
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p. 915 - 919
(2007/10/03)
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- ERbeta ligands. Part 1: the discovery of ERbeta selective ligands which embrace the 4-hydroxy-biphenyl template.
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The synthesis and structure-activity relationships of a series of simple biphenyls is described. Optimization of the 4-hydroxy-biphenyl template led to compounds with ERbeta selectivity on the order of 20-70-fold.
- Edsall Jr., Richard J,Harris, Heather A,Manas, Eric S,Mewshaw, Richard E
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p. 3457 - 3474
(2007/10/03)
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- Ionic Liquid Acceleration of Solid-Phase Suzuki-Miyaura Cross-Coupling Reactions
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(Equation Presented) Room-temperature ionic liquids promote various transition metal-catalyzed reactions in the solution phase. Here, for the first time, we show that these effects are translatable to solid-phase reactions. The Suzuki-Miyaura cross-coupli
- Revell, Jefferson D.,Ganesan
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p. 3071 - 3073
(2007/10/03)
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