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Find video protocols related to scientific articles indexed in Pubmed.
Rhodium(iii)-catalyzed C-H/C-C activation sequence: vinylcyclopropanes as versatile synthons in direct C-H allylation reactions.
Chem. Commun. (Camb.)
PUBLISHED: 11-11-2014
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Succession of C-H activation and C-C activation was achieved by using a single rhodium(iii) catalyst. Vinylcyclopropanes were used as versatile coupling partners. Mechanistic studies suggest that the olefin insertion step is rate-determining and a facile ?-carbon elimination is involved, which represents a novel ring opening mode of vinylcyclopropanes.
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Palladium-catalyzed remote C(sp3)-H arylation of 3-pinanamine.
Org. Lett.
PUBLISHED: 08-04-2014
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3-Pinanamine is a prevalent motif in medicinal chemistry and asymmetric synthesis. In line with the pursuit of novel 3-pinanamine based anti-influenza virus A agent, the direct functionalization of 3-pinanamine was achieved by using Pd-catalyzed C(sp(3))-H activation logic. Good substrate scope and functional group tolerance were observed. The reaction represents a rare example of a direct functionalization of an aliphatic amine at the remote ? position.
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[3]Dendralene synthesis: rhodium(III)-catalyzed alkenyl C-H activation and coupling reaction with allenyl carbinol carbonate.
Angew. Chem. Int. Ed. Engl.
PUBLISHED: 08-01-2013
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[3]DendrAl(l)ene! A new synthesis of [3]dendralenes is based on a Rh(III) -catalyzed alkenyl C?H activation and coupling reaction with allenyl carbinol carbonates (see scheme; DG=directing group). A variety of [3]dendralenes with diverse substitution patterns are accessible with good efficiency. The reaction is highly stereoselective and compatible with different directing groups and numerous functional groups.
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Rh[III]-Catalyzed C-H Amidation Using Aroyloxycarbamates To Give N-Boc Protected Arylamines.
Org. Lett.
PUBLISHED: 05-31-2013
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The Rh(III)-catalyzed amidation of C(sp(2))-H bonds by the use of electron-deficient aroyloxycarbamates as efficient electrophilic amidation partners is reported. The reaction proceeded under mild conditions with broad functional group tolerance, and pyridine and O-methyl hydroxamic acids serve as efficient directing groups, giving access to valuable N-Boc protected arylamines (also Fmoc and Cbz). Preliminary mechanistic experiments are discussed.
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Rh[III]-catalyzed direct C-H amination using N-chloroamines at room temperature.
Org. Lett.
PUBLISHED: 12-23-2011
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An efficient Rh(III)-catalyzed direct C-H amination of N-pivaloyloxy benzamides with N-chloroamines proceeding at room temperature was achieved. The versatile directing group allows for selective mono- and diamination and can be readily converted to give valuable benzamide or aminoaniline derivatives. Mechanistic studies have been carried out to elucidate the reaction pathway.
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Palladium-catalyzed intramolecular C(sp2)-H amidination by isonitrile insertion provides direct access to 4-aminoquinazolines from N-arylamidines.
Org. Lett.
PUBLISHED: 08-05-2011
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An efficient method for the synthesis of 4-amino-2-aryl(alkyl)quinazolines from readily available N-arylamidines and isonitriles via palladium-catalyzed intramolecular aryl C-H amidination by isonitrile insertion has been developed.
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The effect of nitric oxide on the pressure of the acutely obstructed ureter.
Urol. Res.
PUBLISHED: 06-02-2011
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Acute ureteral obstruction leads to changes in pressure inside the ureter, interrupting ureter function. The aim of our study is to explore the relationship between nitric oxide (NO) concentration and pressure in the ureter and to observe the effects of nitric oxide on the revival of renal function. We created the animal models by embedding balloons in the lower ureters of anesthetized dogs and expanding them to simulate acute ureteral obstruction. First, the test animals were pre-treated intravenously with different doses of L-NAME (non-selective nitric oxide synthase inhibitor) to inhibit nitric oxide synthase (NOS), and 10 min later, each subject was administered an intravenous dose of isoproterenol (10 ?g/kg). We measured ureter pressure (UP), total and peak concentrations of NO (using an NO monitor, model inNO-T) in ureteral urine, and the volume of the urine (UFV) leaking from the balloon edge. After a certain amount of time had elapsed, it became clear that the dose of L-NAME was inversely related to the total and peak concentrations of NO, the rate of change in UP, and the volume of urine produced. We conclude that L-NAME prevents the NOS from inhibiting the release of NO, then inhibits the effect of isoproterenol reducing the pressure of the acute obstructive ureter. Inversely, we think that NO can reduce the pressure of the acute obstructive ureter and make the obstructive ureter recanalization. And when more the concentration of nitric oxide, the more the pressure will be reduced, and more urine will be collected.
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A direct intramolecular C-H amination reaction cocatalyzed by copper(II) and iron(III) as part of an efficient route for the synthesis of pyrido[1,2-a]benzimidazoles from N-aryl-2-aminopyridines.
J. Am. Chem. Soc.
PUBLISHED: 09-09-2010
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A novel and efficient synthesis of pyrido[1,2-a]benzimidazoles through direct intramolecular aromatic C-H amination of N-aryl-2-aminopyridines has been developed. The reaction, cocatalyzed by Cu(OAc)(2) and Fe(NO(3))(3)ยท9H(2)O, is carried out in DMF under a dioxygen atmosphere. Diversified pyrido[1,2-a]benzimidazoles containing various substitution patterns are obtained in moderate to excellent yields by using this procedure. The results of mechanistic studies suggest that a Cu(III)-catalyzed electrophilic aromatic substitution (S(E)Ar) pathway is operating in this process. The unique role of iron(III) is believed to lie in its ability to facilitate formation of the more electrophilic Cu(III) species. In the absence of iron(III), a much less efficient and reversible Cu(II)-mediated S(E)Ar process takes place.
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Mild Rh(III)-catalyzed C-H activation and annulation with alkyne MIDA boronates: short, efficient synthesis of heterocyclic boronic acid derivatives.
J. Am. Chem. Soc.
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Taking advantage of Rh(III)-catalyzed C-H activation reactions, we have developed a mild, short, and efficient method for the synthesis of bench-stable 3-isoquinolone MIDA boronates. The reaction is practical and scalable. The product formed has been applied in the Suzuki-Miyaura reaction with high efficiency. This strategy has also been successfully expanded to the synthesis of MIDA boronate functionalized heterocycles such as isoquinoline, pyrrole, and indole.
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Rhodium(III) and hexabromobenzene-a catalyst system for the cross-dehydrogenative coupling of simple arenes and heterocycles with arenes bearing directing groups.
Angew. Chem. Int. Ed. Engl.
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C(6)Br(six) & drugs! C(6)Br(6) can be used as the cooxidant/catalyst modifier for the [Rh(III)Cp*]-catalyzed (Cp*=C(5)Me(5)) dehydrogenative cross-coupling of benzamides with simple benzene derivatives (see scheme, DG=directing group). Similarly, heterocycles can be coupled and druglike structures formed. Mechanistic studies suggest a unique and multiple role of the Cu(OAc)(2)/C(6)Br(6) system and a nonchelate-assisted C-H activation as the rate-determing step.
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Mild rhodium(III)-catalyzed C-H activation and intermolecular annulation with allenes.
Angew. Chem. Int. Ed. Engl.
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All(enes) great! A novel Rh(III)-catalyzed oxidative coupling with allenes under mild conditions provides heterocycles with exocyclic double bonds. This reaction features low catalyst loadings, high regio- and stereoselectivity, and excellent substrate scope. The products were derivatized and preliminary mechanistic studies were conducted.
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