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Cobalt‐Catalyzed Electrophilic Amination of Aryl‐ and Heteroarylzinc Pivalates with N‐Hydroxylamine Benzoates
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Dr. Yi‐Hung Chen Simon Graßl Prof. Dr. Paul Knochel 《Angewandte Chemie (International ed. in English)》2018,57(4):1108-1111
Aryl‐ and heteroarylzinc pivalates can be aminated with O‐benzoylhydroxylamines at 25 °C within 2–4 h in the presence of 2.5–5.0 % CoCl2?2 LiCl to furnish the corresponding tertiary arylated or heteroarylated amines in good yields. This electrophilic amination also provides access to diarylamines and aryl(heteroaryl)amines. A new tuberculosis drug candidate (Q203) was prepared in six steps and 56 % overall yield by using this cobalt‐catalyzed amination as the key step. 相似文献
2.
D. G. Chikhichin V. A. Kotseruba N. V. Gerbeleu G. A. Timko Yu. L. Malaeshtyan G. L. Kamalov 《Theoretical and Experimental Chemistry》2007,43(2):90-96
It was found that during the liquid-phase oxidation of cyclohexene (CH) by air (323–343 K) in the presence of a series of
homo-and heteronuclear μ
3-oxotrimetallohexapivalates with a M2M′O (M, M′ = Co, Cr, Fe, Ni) core insignificant amounts of the corresponding epoxide are formed, and 3-hydroperoxy-2-cyclohexene
(HP), 3-hydroxy-2-cyclohexene (CHol), and 2-cyclohexen-3-one (CHone) accumulate in the oxidate. It is suggested that CHone
and CHol are “dead-end” products from the oxidation of CH under the investigated conditions while the HP is a unique “intermediate-damper”
that gives rise to the realization of alternative paths (catalytic cycles) for the formation of these products.
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Translated from Teoreticheskaya i éksperimental’naya Khimiya, Vol. 43, No. 2, pp. 85–90, March–April, 2007. 相似文献
3.
E. Yu. Fursova O. V. Kuznetsova V. I. Ovcharenko G. V. Romanenko A. S. Bogomyakov 《Russian Chemical Bulletin》2008,57(6):1198-1205
The reaction of NiCl2 with excess potassium pivalate (KPiv) in ethanol affords the chainpolymeric compound KNi4(Piv)7(OH)2(EtOH)6. In the solid compound, the tetranuclear nickel fragments alternate with potassium atoms. The use of KNi4(Piv)7(OH)2(EtOH)6 in the reaction with Ni(hfac)2 (hfac is the hexafluoroacetylacetonate anion) gave the first polynuclear mixed-ligand complexes [K2Ni6(Piv)7(hfac)3(OH)4(HPiv)2(Me2CO)2]·1.5C7H16, [Ni6(Piv)4(hfac)4(OH)4(Me2CO)4], [K2Ni8(Piv)8(hfac)4(OH)6(H2O)2(Me2CO)6], [Ni8(Piv)10(hfac)2(OH)2(MeO)2(MeOH)2(HPiv)2]·C6H14, and [Ni16(Piv)10(hfac)6(OH)10(MeO)6(MeOH)8(H2O)6]·C6H14 containing both Piv and hfac as the anionic ligands. The molecular and crystal structures of all these compounds were established,
and their magnetic properties were studied. All solids containing simultaneously Piv and hfac ligands tend to undergo ferromagnetic
ordering with decreasing temperature. The solid [Ni8(Piv)10(hfac)2(OH)2(MeO)2(MeOH)2(HPiv)2]·C6H14 undergoes cooperative magnetic ordering below T
c (2.5 K).
Dedicated to the 90th anniversary of the L. Ya. Karpov Institute of Physical Chemistry.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1175–1182, June, 2008. 相似文献
4.
Dr. Yi-Hung Chen Carl Phillip Tüllmann Dr. Mario Ellwart Prof. Dr. Paul Knochel 《Angewandte Chemie (International ed. in English)》2017,56(31):9236-9239
We report the preparation of solid and air-stable polyfunctionalized alkynylzinc pivalates from the corresponding alkynes using TMPZnOPiv (TMP=2,2,6,6-tetramethylpiperidyl) as base. These organozinc pivalates are obtained as powders under mild conditions in excellent yields and can be manipulated in air for several hours without significant decomposition. These zinc reagents show an excellent reactivity in various carbon–carbon bond- forming reactions and 1,3-dipolar cycloadditions. An alkynylzinc pivalate has been used to prepare a carboxyamidotriazole with potential antineoplastic activity in eight steps and 38 % overall yield. 相似文献
5.
Theoretical prediction on the synthesis of 2,3‐dihydropyridines through Co(III)‐catalysed reaction of unsaturated oximes with alkenes
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Xiang‐Biao Zhang Bin‐Bin Yu Sheng‐Meng Si Song Wang 《International journal of quantum chemistry》2017,117(8)
Cobalt‐based catalysts can replace the homologous group‐9 rhodium‐based ones. Herein, we used density functional theory (DFT) calculations to predict the synthesis of 2,3‐dihydropyridines using α,β‐unsaturated oxime pivalates and alkenes catalysed by [Cp*CoOAc]+ instead of [Cp*RhOAc]+. The catalytic cycle involves reversible acetate‐assisted metalation‐deprotonation, migratory insertion of alkenes, and reductive elimination/N‐O cleavage. The migratory insertion of alkenes was determined to be the rate‐determining step, and the reaction is irreversible due to the strongly exergonic reductive elimination/N? O cleavage. When using the CF3‐substituted Cp*Co(III) catalyst, the apparent activation energy indicates that the title reaction can proceed at higher temperatures. Electron‐withdrawing substituent groups on Cp* facilitate the reaction. In contrast, substituting phenyl with the electron‐deficient p‐CF3‐phenyl at the 2‐position of α,β‐unsaturated oxime pivalate hinders the reaction, and so does the use of polarized alkenes with electron‐withdrawing substituent groups 相似文献
6.
Irina Fomina Zhanna Dobrokhotova Grygory Aleksandrov Artem Bogomyakov Matvey Fedin Alexander Dolganov Tatyana Magdesieva Vladimir Novotortsev Igor Eremenko 《Polyhedron》2010
Tetrabridged dinuclear complexes ((2-NH2)C5H4N)2Cu2(μ2-OOCCMe3)4 (2·С6Н6) and ((3-NH2)C5H4N)2Cu2(μ2-OOCCMe3)4 (3) and the cocrystallization product ((4-NMe2)C5H4N)2Cu(η2–OOCCMe3)2·2((4-NMe2)C5H4N)2Cu2(μ2-OOCCMe3)4 (4) were synthesized by the reaction of the polymer [Cu(OOCCMe3)2]n (1) with aminopyridine ligands (L) of different nature (Cu: L = 1:1) in С6Н6. The solid-state thermal decomposition of these compounds was studied by differential scanning calorimetry and thermogravimetry, and their electrochemical behavior was investigated by cyclic voltammetry. All newly synthesized complexes were studied by X-ray diffraction, the magnetic properties of the complexes were investigated, and ESR measurements were performed. 相似文献
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