Relevant bibliographies by topics / Diaminocarbenes

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Academic literature on the topic 'Diaminocarbenes'

Author: Grafiati
Published: 4 June 2021
Last updated: 17 February 2022

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Journal articles on the topic "Diaminocarbenes"

1

Mikhaylov, Vladimir, Viktor Sorokoumov, Denis Liakhov, Alexander Tskhovrebov, and Irina Balova. "Polystyrene-Supported Acyclic Diaminocarbene Palladium Complexes in Sonogashira Cross-Coupling: Stability vs. Catalytic Activity." Catalysts 8, no. 4 (April 2, 2018): 141. http://dx.doi.org/10.3390/catal8040141.

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Two types of immobilized on the amino-functionalized polystyrene-supported acyclic diaminocarbene palladium complexes (ADC-PdII) are investigated under Sonogashira cross-coupling conditions. Depending on substituents in the diaminocarbene fragment immobilized ADC-PdII, systems are found to have different catalytic activity and stability regarding Pd-leaching. PdII-diaminocarbenes possessing protons at both nitrogen atoms smoothly decompose into Pd0-containing species providing a catalytic “cocktail system” with high activity and ability to reuse within nine runs. Polymer-supported palladium (II) complex bearing NBn–Ccarbene–NH-moiety exhibits greater stability while noticeably lower activity under Sonogashira cross-coupling. Four molecular ADC-PdII complexes are also synthesized and investigated with the aim of confirming proposed base-promoted pathway of ADC-PdII conversion through carbodiimide into an active Pd0 forms.
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Marchenko, Anatoliy, Georgyi Koidan, Anastasiya Hurieva, Olena Kurpiieva, Yurii Vlasenko, Alexander B. Rozhenko, and Aleksandr Kostyuk. "StableN-Phosphanyl Acyclic Diaminocarbenes." European Journal of Inorganic Chemistry 2014, no. 20 (June 12, 2014): 3259–70. http://dx.doi.org/10.1002/ejic.201402166.

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Marchenko, Anatoliy, Georgyi Koidan, Anastasiya Hurieva, Yurii Vlasenko, Aleksandr Kostyuk, and Andrea Biffis. "Correction: Palladium(ii) complexes with chelating N-phosphanyl acyclic diaminocarbenes: synthesis, characterization and catalytic performance in Suzuki couplings." Dalton Transactions 45, no. 4 (2016): 1779. http://dx.doi.org/10.1039/c5dt90223a.

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Correction for ‘Palladium(ii) complexes with chelating N-phosphanyl acyclic diaminocarbenes: synthesis, characterization and catalytic performance in Suzuki couplings’ by Anatoliy Marchenko et al., Dalton Trans., 2016, DOI: 10.1039/c5dt02250a.
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4

Alder, Roger W., Michael E. Blake, Leila Chaker, Jeremy N. Harvey, François Paolini, and Jan Schütz. "When and How Do Diaminocarbenes Dimerize?" Angewandte Chemie International Edition 43, no. 44 (September 29, 2004): 5896–911. http://dx.doi.org/10.1002/anie.200400654.

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Schulz, Tim, Daniel Weismann, Lars Wallbaum, Robin Guthardt, Charlotte Thie, Michael Leibold, Clemens Bruhn, and Ulrich Siemeling. "New Stable and Persistent Acyclic Diaminocarbenes." Chemistry – A European Journal 21, no. 40 (August 25, 2015): 14107–21. http://dx.doi.org/10.1002/chem.201502315.

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Rosen, Evelyn L., Daphne H. Sung, Zheng Chen, Vincent M. Lynch, and Christopher W. Bielawski. "Olefin Metathesis Catalysts Containing Acyclic Diaminocarbenes." Organometallics 29, no. 1 (January 11, 2010): 250–56. http://dx.doi.org/10.1021/om9008718.

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Shevchenko, Igor V., Kostiantyn V. Turcheniuk, Andrey A. Kirilchuk, Jerzy Leszczynski, and Alexander B. Rozhenko. "On the Reaction of Diaminocarbenes with Aroylimines." Journal of Organic Chemistry 80, no. 3 (January 13, 2015): 1387–94. http://dx.doi.org/10.1021/jo502155j.

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Tskhovrebov, Alexander G., Konstantin V. Luzyanin, Fedor M. Dolgushin, M. Fátima C. Guedes da Silva, Armando J. L. Pombeiro, and Vadim Yu Kukushkin. "Novel Reactivity Mode of Metal Diaminocarbenes: Palladium(II)-Mediated Coupling between Acyclic Diaminocarbenes and Isonitriles Leading to Dinuclear Species." Organometallics 30, no. 12 (June 27, 2011): 3362–70. http://dx.doi.org/10.1021/om2002574.

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Cheng, Mu-Jeng, and Ching-Han Hu. "A computational study on the stability of diaminocarbenes." Chemical Physics Letters 322, no. 1-2 (May 2000): 83–90. http://dx.doi.org/10.1016/s0009-2614(00)00388-2.

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Melaimi, Mohand, Michèle Soleilhavoup, and Guy Bertrand. "Stable Cyclic Carbenes and Related Species beyond Diaminocarbenes." Angewandte Chemie International Edition 49, no. 47 (September 10, 2010): 8810–49. http://dx.doi.org/10.1002/anie.201000165.

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Dissertations / Theses on the topic "Diaminocarbenes"

1

Gupta, Shilpi. "Synthesis, delocalization and reactivity in stable diaminocarbenes." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 1999. http://www.collectionscanada.ca/obj/s4/f2/dsk1/tape7/PQDD_0003/MQ45513.pdf.

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Blake, Michael Edward. "The preparation and study of unhindered diaminocarbenes." Thesis, University of Bristol, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.299313.

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Rodezno, José M. "Transformation of formaldehyde aminals into diaminocarbenes and carbenium salts." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2001. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp04/MQ58760.pdf.

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Mankou, Makaya Amelle Amandine. "Nouveaux potentiels du noyau imidazole en chimie de coordination de ligands phospho-carbonés : effets de charge et versions chirales." Thesis, Toulouse 3, 2016. http://www.theses.fr/2016TOU30258/document.

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Les travaux réalisés au cours de cette thèse sont centrés sur la synthèse et la réactivité de ligands phosphorés à caractère faiblement s-donneur et fortement p-accepteur. Il s'agit de ligands phosphines présentant une charge cationique en position a de l'atome de phosphore. Cette charge positive est amenée alternativement par un fragment amidinium ou bien cyclopropénium, conduisant respectivement aux amidinio- et cyclopropéniophosphines. Ces travaux sont présentés en trois chapitres. Dans le premier chapitre, après un partie bibliographique, nous avons décrit la synthèse de di-imidazolo- et di-imidazoliophosphines diversement P-substituées par des groupements aryle, alkyle et di(alkyl)amino. L'étude de la réactivité de ces ligands vis-à-vis d'acides de Lewis métalliques ou non a permis de démontrer que la nature du substituant porté par l'atome de phosphore influençait de façon critique les propriétés de coordination. Divers complexes métalliques et oxydes de phosphines ont été ainsi obtenus et entièrement caractérisés. Dans le deuxième chapitre, nous nous sommes intéressés à la préparation de phosphines a-cationiques chirales. Deux cas distincts ont été ainsi considérés : des phosphines cationiques à chiralité électrostatique dans lesquelles l'effet électrostatique prime sur l'effet stérique et des phosphines cationiques à chiralité stérique dans lesquelles l'effet stérique est cette fois-ci prédominant. Il a été démontré qu'en dépit des effets électroniques et stériques présents, ces phosphines étaient capables de se coordiner à un centre métallique. Divers complexes de métaux de transition de ces phosphines P-chirogènes ont été ainsi préparés et entièrement caractérisés. Dans le cas des phosphines à chiralité électrostatique, une version énantiopure a été isolée grâce à l'utilisation d'un complexe de palladium(II) orthométallé optiquement actif comme agent de dédoublement. Le troisième chapitre est axé sur le développement de ligands carbonés anioniques fortement donneurs de type imidazolyle et de leurs complexes. Afin de contre-balancer l'extrémité carbonée donneuse, une partie phosphorée acceptrice de type imidazolophosphine a été introduite. En série rhodium(I), deux complexes de ces ligands chélatants hybrides phospho-carbonés ont été ainsi isolés et caractérisés
The project developed during this PhD thesis aims at the synthesis and reactivity of phosphorus ligands with weak s-donor and strong p-acceptor properties. They correspond to phosphine ligands featuring a cationic charge in a position of the phosphorus atom. The cationic charge can be introduced alternatively through an amidinium or a cyclopropenium moiety affording amidinio- and cyclopropeniophosphines, respectively. In the first chapter, after a bibliographical section, the synthesis of di-imidazolo- and di-imidazoliophosphines with aryl, alkyl and dialkylamino P-substituents is described. The study of the reactivity of these phosphine ligands towards metallic (or not) Lewis acids demonstrates that the nature of the P-substituent influences dramatically the corresponding coordination properties. Various cationic metal complexes and phosphine oxides are obtained and fully characterized. The second chapter of the thesis is focused on the development of chiral a-cationic phosphines. Two different cases are considered: cationic phosphines with electrostatic chirality where steric effects may be neglected and cationic phosphines with predominant steric chirality. In both cases, despite electron-poor character, these phosphines were shown to coordinate various transition metal centers. In the case of phosphines featuring electrostatic chirality, a representative was isolated in an optically pure form through the use of chiral orthometallated palladium(II) complexes as resolving agents. Finally, the third chapter concerns the development of imidazolyl carbon ligands and the corresponding complexes. In order to balance the electron-richness of the anionic imidazolyl donor extremity, an electron-poor phosphorus coordinating end, namely an imidazolophosphine is introduced. In the rhodium(I) series, two chelating complexes of these hybrid 'rich-poor' carbon-phosphorus ligands have been isolated and characterized
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Ellison, Matthew Christopher. "Ligand Effects in Gold(I) Acyclic Diaminocarbene Complexes and Their Influence on Regio- and Enantioselectivity of Homogeneous Gold(I) Catalysis." Thesis, University of North Texas, 2019. https://digital.library.unt.edu/ark:/67531/metadc1538722/.

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This dissertation focuses on the computational investigation of gold(I) acyclic diaminocarbene (ADC) complexes and their application in homogeneous gold(I) catalysis. Chapter 2 is an in-depth computational investigation of the σ- and π-bonding interactions that make up the gold-carbene bond. Due to the inherent conformation flexibility of ADC ligands, distortions of the carbene plane can arise that disrupt orbital overlap between the lone pairs on the adjacent nitrogen atoms and the empty p-orbital of the carbene. This study investigated the affect these distortions have on the strength of the σ- and π-bonding interactions. This investigation demonstrated that while these distortions can affect the σ- and π-bonding interactions, the ADC ligand have to become highly distorted before any significant change in energy of either the σ- or π-bonding interactions occurs. Chapter 3 is a collaborative investigation between experimental and computational methods, DFT calculations were employed to support the experimental catalytic results and determine the role that steric effects have in controlling the regioselectivity of a long-standing electronically controlled gold(I)-catalyzed tandem 1,6-enyne cyclization/hydroarylation reaction with indole. This study demonstrated that by sterically hindering nucleophilic attack of indole at the favored position, nucleophilic attack would occur at a secondary position leading to the selective formation of the electronically unfavored product. Chapter 4 is a collaborative investigation between experimental and computational methods. DFT calculations were employed to investigate and rationalize the importance of secondary non-covalent interactions and their influence on the enantioselectivity of a gold(I)-catalyzed intramolecular hydroamination of allene reaction. Through computational investigation of the enantiodetermining step, and the non-covalent interactions present between 2′-aryl substituent and the rest of the catalyst, it was determined that the presence of CF3 group on the 3,5-position of the 2′-aryl ring is crucial to maintaining a more rigid chiral pocket leading to higher enantiomeric excesses in this dynamic system. This increased rigidity is believed to be attributable to the several weak non-covalent interactions that arise between the allene substrate or diisopropyl N-substituent and the fluorine atoms of the CF3 groups.
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6

Ellison, Matthew Christopher. "Ligand Effects in Gold[I] Acyclic Diaminocarbene Complexes and Their Influence on Regio- and Enantioselectivity of Homogeneous Gold[I] Catalysis." Thesis, University of North Texas, 2008. https://digital.library.unt.edu/ark:/67531/metadc1538722/.

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This dissertation focuses on the computational investigation of gold(I) acyclic diaminocarbene (ADC) complexes and their application in homogeneous gold(I) catalysis. Chapter 2 is an in-depth computational investigation of the σ- and π-bonding interactions that make up the gold-carbene bond. Due to the inherent conformation flexibility of ADC ligands, distortions of the carbene plane can arise that disrupt orbital overlap between the lone pairs on the adjacent nitrogen atoms and the empty p-orbital of the carbene. This study investigated the affect these distortions have on the strength of the σ- and π-bonding interactions. This investigation demonstrated that while these distortions can affect the σ- and π-bonding interactions, the ADC ligand have to become highly distorted before any significant change in energy of either the σ- or π-bonding interactions occurs. Chapter 3 is a collaborative investigation between experimental and computational methods, DFT calculations were employed to support the experimental catalytic results and determine the role that steric effects have in controlling the regioselectivity of a long-standing electronically controlled gold(I)-catalyzed tandem 1,6-enyne cyclization/hydroarylation reaction with indole. This study demonstrated that by sterically hindering nucleophilic attack of indole at the favored position, nucleophilic attack would occur at a secondary position leading to the selective formation of the electronically unfavored product. Chapter 4 is a collaborative investigation between experimental and computational methods. DFT calculations were employed to investigate and rationalize the importance of secondary non-covalent interactions and their influence on the enantioselectivity of a gold(I)-catalyzed intramolecular hydroamination of allene reaction. Through computational investigation of the enantiodetermining step, and the non-covalent interactions present between 2′-aryl substituent and the rest of the catalyst, it was determined that the presence of CF3 group on the 3,5-position of the 2′-aryl ring is crucial to maintaining a more rigid chiral pocket leading to higher enantiomeric excesses in this dynamic system. This increased rigidity is believed to be attributable to the several weak non-covalent interactions that arise between the allene substrate or diisopropyl N-substituent and the fluorine atoms of the CF3 groups.
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Kong, Fanji. "Synthesis and Application of New Chiral Ligands for Enantioselectivity Tuning in Transition Metal Catalysis." Thesis, University of North Texas, 2017. https://digital.library.unt.edu/ark:/67531/metadc1011774/.

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A set of five new C3-symmetric phosphites were synthesized and tested in palladium-catalyzed asymmetric Suzuki coupling. The observed reactivity and selectivity were dependent upon several factors. One of the phosphites was able to achieve some of the highest levels of enantioselectivity in asymmetric Suzuki couplings with specific substrates. Different hypotheses have been made for understanding the ligand effects and reaction selectivities, and those hypotheses were tested via various methods including DOSY NMR experiments, X-ray crystallography, and correlation of catalyst selectivity with Tolman cone angles. Although only modest enantioselectivities were observed in most reactions, the ability to synthesis these phosphites in only three steps on gram scales and to readily tune their properties by simple modification of the binaphthyl 2´-substituents makes them promising candidates for determining structure-selectivity relationships in asymmetric transition metal catalysis, in which phosphites have been previously shown to be successful. A series of novel chiral oxazoline-based carbodicarbene ligands was targeted for synthesis. Unfortunately, the chosen synthetic route could not be completed due to unwanted reactivity of the oxazoline ring. However, a new and efficient route for Pd-catalyzed direct amination of aryl halides with oxazoline amine was developed and optimized during these studies. Chiral binaphthyl based Pd(II) ADC complexes with different substituent groups have been synthesized and tested in asymmetric Suzuki coupling reactions. Although only low enantioselectivities were observed in Suzuki coupling, this represents a new class of chiral metal-ADC catalysts that could be tested in further catalytic.
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8

Schulz, Tim [Verfasser]. "Die Carbonylierung acyclischer Diaminocarbene / Tim Schulz." Kassel : Universitätsbibliothek Kassel, 2014. http://d-nb.info/1059275511/34.

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Collins, Lee. "Diamido- and diaminocarbene complexes of the late d-block metals." Thesis, University of Bath, 2016. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.687383.

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Zhang, Xiaofan. "Synthesis, Characterization and Catalytic Studies of Chiral Gold Acyclic Diaminocarbene Complexes." Thesis, University of North Texas, 2016. https://digital.library.unt.edu/ark:/67531/metadc862827/.

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Chiral gold complexes have been applied in homogeneous catalytic reactions since 1986, in some cases with high enantioselectivity. Acyclic diaminocarbene (ADC) ligands are acyclic analogues of N-heterocyclic carbenes (NHCs) that have larger N-CCarbene-N angles and stronger donating ability. ADCs have been developed as alternatives to phosphine and NHC ligands in homogeneous gold catalysis. In 2012, a new series of chiral gold(I) ADCs were first developed by Slaughter's group and were shown to give remarkable enantioselectivities in some reactions. Because of the hindered rotation of the N-CCarbene bonds of ADC, chiral ADC substituents can easily get close to the metal center in some conformations, although two rotameric structures are formed if the chiral amine is nonsymmetric. The selective of specific ADC conformations was the initial focus of this study. Formational selectivity of one diastereomer of an ADC ligand during synthesis was examines by measuring the relative rates of diastereomer formation in a 1H NMR kinetic study. The potential for converting multiple conformational isomers of ADCs into a single conformation, or at least a simpler mixture, was examined. This study used the analogy that anti- isomer has electronic and structural similarity with urea/thiourea, raising the possibility that 1,8-naphthyridine can be used to favor certain conformations through a self-assembled hydrogen-bonding complex. Gold(I) is a soft carbophilic Lewis acid able to active C-C π bonds to nucleophilic attack, and ADC-gold complexes are potentially useful in this regard. Therefore, biaryl gold(I) ADC complexes were examine with silver salt additives in catalytic 1,6-enyne cyclization reaction. A detailed study found that the counteranion affects the regioselectivities of these reactions more than substituents on the ancillary ADC ligands.
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Books on the topic "Diaminocarbenes"

1

Gupta, Shilpi. Synthesis, delocalization and reactivity in stable diaminocarbenes. Ottawa: National Library of Canada, 1999.

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Gupta, Shilpi. Synthesis, delocalization and reactivity in stable diaminocarbenes. 1999.

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Rodezno, Jose M. Transformation of formaldehyde aminals into diaminocarbenes and carbenium salts. 2001.

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Book chapters on the topic "Diaminocarbenes"

1

Castilho, T. J., M. F. C. Guedes Da Silva, A. J. L. Pombeiro, R. Bertani, M. Mozzon, and R. A. Michelin. "Electrochemical Behaviour of Aminooxy-, Dioxy- and Diaminocarbene Complexes of Palladium(II) and Platinum(II)." In Molecular Electrochemistry of Inorganic, Bioinorganic and Organometallic Compounds, 345–50. Dordrecht: Springer Netherlands, 1993. http://dx.doi.org/10.1007/978-94-011-1628-2_31.

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2

Boyarskiy, Vadim P., Konstantin V. Luzyanin, and Vadim Yu Kukushkin. "Palladium-(Acyclic Diaminocarbene) Species as Alternative to Palladium-(Nitrogen Heterocyclic Carbenes) in Cross-Coupling Catalysis." In Advances in Organometallic Chemistry and Catalysis, 145–55. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2013. http://dx.doi.org/10.1002/9781118742952.ch11.

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Alder, Roger. "Diaminocarbenes." In Carbene Chemistry. CRC Press, 2002. http://dx.doi.org/10.1201/9780203910924.ch5.

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