- Copper-catalyzed oxidative benzylic C(sp3)-H amination: Direct synthesis of benzylic carbamates
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A new efficient strategy to access benzylic carbamates through C-H activation is reported. The use of a catalytic amount of a Cu(i)/diimine ligand in combination with NFSI ((PhSO2)2NF) or F-TEDA-PF6 as oxidants and H2NCO2R as an amine source directly leads to the C-N bond formation at the benzylic position. The mild reaction conditions and the broad substrate scope make this transformation a useful method for the late-stage incorporation of a ubiquitous carbamate fragment onto hydrocarbons. This journal is
- Liu, Shuai,Achou, Rapha?l,Boulanger, Coline,Pawar, Govind,Kumar, Nivesh,Lusseau, Jonathan,Robert, Frédéric,Landais, Yannick
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supporting information
p. 13013 - 13016
(2020/11/05)
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- Copper-catalyzed formal transfer hydrogenation/deuteration of aryl alkynes
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A copper-catalyzed reduction of alkynes to alkanes and deuterated alkanes is described under transfer hydrogenation and transfer deuteration conditions. Commercially available alcohols and silanes are used interchangeably with their deuterated analogues as the hydrogen or deuterium sources. Transfer deuteration of terminal and internal aryl alkynes occurs with high levels of deuterium incorporation. Alkyne-containing complex natural product analogues undergo transfer hydrogenation and transfer deuteration selectively, in high yield. Mechanistic experiments support the reaction occurring through a cis-alkene intermediate and demonstrate the possibility for a regioselective alkyne transfer hydrodeuteration reaction.
- Sloane, Samantha E.,Reyes, Albert,Vang, Zoua Pa,Li, Lingzi,Behlow, Kiera T.,Clark, Joseph R.
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supporting information
p. 9139 - 9144
(2020/11/30)
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- REAGENTS AND PROCESS FOR DIRECT C-H FUNCTIONALIZATION
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Thianthrene derivative of the Formula (I): wherein R1 to R8 may be the same or different and are selected from hydrogen, Cl, F, a partially or fully fluorinated C1 to C6 alkyl group, and wherein n is 0 or 1, with the proviso that at least one of R1 to R8 is not hydrogen and process for C-H functionalization of aromatic compounds using this compound.
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Page/Page column 113; 114
(2020/06/01)
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- Selective hydrodeoxygenation of hydroxyacetophenones to ethyl-substituted phenol derivatives using a FeRu?SILP catalyst
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The selective hydrodeoxygenation of hydroxyacetophenone derivatives is achieved opening a versatile pathway for the production of valuable substituted ethylphenols from readily available substrates. Bimetallic iron ruthenium nanoparticles immobilized on an imidazolium-based supported ionic liquid phase (Fe25Ru75?SILP) show high activity and stability for a broad range of substrates without acidic co-catalysts. This journal is
- Bordet, Alexis,Goclik, Lisa,Leitner, Walter,Offner-Marko, Lisa
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supporting information
p. 9509 - 9512
(2020/09/02)
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- Site-Selective C?H Oxygenation via Aryl Sulfonium Salts
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Herein, we report a two-step process forming arene C?O bonds in excellent site-selectivity at a late-stage. The C?O bond formation is achieved by selective introduction of a thianthrenium group, which is then converted into C?O bonds using photoredox chemistry. Electron-rich, -poor and -neutral arenes as well as complex drug-like small molecules are successfully transformed into both phenols and various ethers. The sequence differs conceptually from all previous arene oxygenation reactions in that oxygen functionality can be incorporated into complex small molecules at a late stage site-selectively, which has not been shown via aryl halides.
- Sang, Ruocheng,Korkis, Stamatis E.,Su, Wanqi,Ye, Fei,Engl, Pascal S.,Berger, Florian,Ritter, Tobias
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supporting information
p. 16161 - 16166
(2019/11/03)
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- Thermal Stability of 4-tert-Butyl Diphenyl Oxide
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Abstract: In the temperature range of 703–763 K, the thermal stability of 4-tert-butyl diphenyl oxide (4?TBDPO) has been studied, the components of the thermolysis reaction mass have been identified, a kinetic model of the process has been proposed, and the rate constants and parameters of the Arrhenius equation for all reactions under consideration have been calculated. The predominant role of isomerization transformations of 4-TBDPO has been found. A mechanism for the radical isomerization of the tert-butyl substituent has been proposed.
- Shakun,Nesterova,Tarazanov,Spiridonov
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p. 2123 - 2130
(2019/11/11)
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- Direct C-C Bond Formation from Alkanes Using Ni-Photoredox Catalysis
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A method for direct cross coupling between unactivated C(sp3)-H bonds and chloroformates has been accomplished via nickel and photoredox catalysis. A diverse range of feedstock chemicals, such as (a)cyclic alkanes and toluenes, along with late-stage intermediates, undergo intermolecular C-C bond formation to afford esters under mild conditions using only 3 equiv of the C-H partner. Site selectivity is predictable according to bond strength and polarity trends that are consistent with the intermediacy of a chlorine radical as the hydrogen atom-abstracting species.
- Ackerman, Laura K. G.,Martinez Alvarado, Jesus I.,Doyle, Abigail G.
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supporting information
p. 14059 - 14063
(2018/10/24)
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- Preparation of carbon nanotube-supported α-Fe2O 3@CuO nanocomposite: A highly efficient and magnetically separable catalyst in cross-coupling of aryl halides with phenols
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Herein, we introduce the first magnetic CuO nanoparticles based on carbon nanotubes as a highly intriguing magnetic catalyst in Ullmann-type coupling of aryl halides with phenols. Two facile procedures were used for the preparation of this magnetically separable catalytic system. Having been treated with FeSO4 and then H2O2, nanotubes accommodated the resulting iron hydroxides on the walls. The resulting nanocomposite was then exposed to argon atmosphere at 450°C giving rise to a carbon nanotube-supported α-Fe2O3 compound. Ultimately, copper acetate was hydrolysed in the presence of CNT supported α-Fe 2O3 at 100°C and our novel catalyst was gained. Some spectroscopic and microscopic techniques such as Infrared spectroscopy (IR), X-ray diffraction spectroscopy (XRD), Vibrational sample magnetometry (VSM), Brunauer-Emmett-Teller (BET), Barrett-Joyner-Halenda (BJH), Inductively coupled plasma (ICP), Scanning electron microscopy (SEM) and Transmission electron microscopy (TEM) corroborated the structure of the catalyst. The catalyst synthesized showed good activity in C-O cross coupling reactions affording the highest rate of completion. Magnetic feature of the catalyst helped facile separation of it from the reaction medium. The catalyst could also be reused up to six times without any loss of its activity.
- Saberi, Dariush,Sheykhan, Mehdi,Niknam, Khodabakhsh,Heydari, Akbar
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p. 2025 - 2031
(2013/07/26)
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