- Synthesis of imidazol-2-ylidenes by reduction of imidazole-2(3H)-thiones
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An improved synthesis of the title compounds is reported. Reaction of the N,N'-dialkylthioureas 1 with 3-hydroxy-2-butanone gives the imidazole-2(3H)-thiones 2 which on treatment with potassium in boiling tetrahydrofuran give the imidazol-2-ylidenes 3 in excellent yields.
- Kuhn,Kratz
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- Steric Properties of N-Heterocyclic Carbenes affect the Performance of Electronic Probes
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Electronic probes of ligands, particularly carbenes, are widely used in assessing electronic properties; the results inform the selection of a ligand for a given application. As such, it is important to ensure the data obtained is reliable and unaffected by other factors, such as the steric bulk of the ligand. The effects of such steric factors on two commonly used electronic probes (based on palladium and selenium) are investigated here, with the selenium adduct found to be particularly sensitive. It is hoped that this serves as a cautionary tale to always critically evaluate what a probe is measuring.
- Barnett, Christopher,Cole, Marcus L.,Harper, Jason B.
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supporting information
p. 4954 - 4958
(2021/12/02)
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- Synthesis of an [(NHC)2Pd(SiMe3)2] complex and catalytic cis-bis(silyl)ations of alkynes with unactivated disilanes
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The novel complex cis-[(ITMe)2Pd(SiMe3)2 (ITMe=1,3,4,5-tetramethylimidazol-2-ylidene) has been synthesized by mild oxidative cleavage of Me3SiSiMe3 using [(ITMe)2Pd0]. The use of this complex as precatalyst for the cis-bis(silyl)ation of alkynes using unactivated disilanes is reported. Double the Si: The novel complex cis-[(ITMe)2Pd(SiMe3)2] (1, ITMe=1,3,4,5-tetramethylimidazol-2-ylidene) has been synthesized by mild oxidative cleavage of Me3SiSiMe3 using [(ITMe)2Pd0]. The synthesized complex was used as a precatalyst for the cis-bis(silyl)ation of alkynes using unactivated disilanes.
- Ansell, Melvyn B.,Roberts, Debbie E.,Cloke, F. Geoffrey N.,Navarro, Oscar,Spencer, John
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supporting information
p. 5579 - 5582
(2015/09/21)
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- Dihalo(imidazolium)sulfuranes: A Versatile Platform for the Synthesis of New Electrophilic Group-Transfer Reagents
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The syntheses of imidazolium thiocyanates and imidazolium thioalkynes from dihalo(imidazolium) sulfuranes are reported and their reactivities as CN+ and R-CC+ synthons evaluated, respectively. The easy and scalable preparation of these electrophilic reagents, their operationally simple handling, broad substrate scope, and functional group tolerance clearly illustrate the potential of these species to become a reference for the direct electrophilic cyanation and alkynylation of organic substrates.
- Talavera, Garazi,Pe?a, Javier,Alcarazo, Manuel
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supporting information
p. 8704 - 8707
(2015/07/27)
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- Imidazolium-based warheads strongly influence activity of water-soluble peptidic transglutaminase inhibitors
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New peptidic water-soluble inhibitors are reported. In addition to the carboxylate moiety, a new polar warhead was explored. Depending on the size of its substituents, the newly appended imidazolium scaffold designed to enhance the hydrophilic character o
- Badarau, Eduard,Mongeot, Alexandre,Collighan, Russell,Rathbone, Dan,Griffin, Martin
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supporting information
p. 526 - 530
(2013/10/01)
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- Activation of a cyclobutanone carbon-carbon bond over an aldehyde carbon-hydrogen bond in the rhodium-catalyzed decarbonylation
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A rhodium(I)-N-heterocyclic carbene complex achieved a high-yield decarbonylation reaction of cyclobutanones to selectively afford cyclopropanes. With this catalyst, a cyclobutanone having an aldehyde moiety underwent chemoselective decarbonylation of the ketonic carbonyl group with the aldehydic carbonyl group left intact. Copyright
- Matsuda, Takanori,Shigeno, Masanori,Murakami, Masahiro
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p. 288 - 289
(2007/10/03)
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- Organometallic precursor for forming metal pattern
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Disclosed is an organometallic precursor for forming a metal pattern, having a structure defined by the following Formula 1, and a method of forming the metal pattern using the same, in which the conductive metal pattern is readily formed through an exposing step without using a photo-resist.Formula 1 L'-M-L ???wherein, M is a transition metal selected from the group consisting of Ag, Au, Cu, Pd, Ni, and Pt; L is an imidazolylidene compound having a structure defined by the following Formula 2; and L' is an imidazolylidene compound having a structure defined by the following Formula 2 or a β-diketonate compound having a structure defined by the following Formula 3: ???wherein, R1, R2, R3, and R4 are independently a hydrogen atom, or alkyl group, alkenyl group, alkynyl group, carboxyl group, alkoxy group, or ester group with 1 to 20 carbons, or aromatic hydrocarbon group with 6 to 20 carbons; and ???wherein, R5, R6, and R7 are independently a hydrogen atom, or alkyl group, alkenyl group, alkynyl group, carboxyl group, alkoxy group, or ester group with 1 to 20 carbons, or aromatic hydrocarbon group with 6 to 20 carbons.
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