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Journal articles on the topic 'Diaminocarbenes'

Author: Grafiati

Published: 4 June 2021

Last updated: 17 February 2022

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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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2

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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3

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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5

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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6

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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7

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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8

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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9

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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10

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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11

Heinemann, Christoph, and Walter Thiel. "Ab initio study on the stability of diaminocarbenes." Chemical Physics Letters 217, no. 1-2 (January 1994): 11–16. http://dx.doi.org/10.1016/0009-2614(93)e1360-s.

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12

Lai, Chin-Hung. "A Comparison of the Lewis Basicity of Diamidocarbenes and Diaminocarbenes." Australian Journal of Chemistry 68, no. 7 (2015): 1084. http://dx.doi.org/10.1071/ch14555.

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In this study, density functional theory calculations, using the M06-2X functional, were performed to investigate the efficiencies of various carbenes in inducing hydrogen abstraction in BH3 through the formation of a Lewis acid–base pair with BH3. The density functional theory results indicate that diamidocarbenes are more efficient in reducing the B–H bond energy of BH3 than diaminocarbenes. Natural bond orbital and combined charge and bond energy analyses were performed to investigate the Lewis acid–base pair formed by BH3 and the title carbenes.

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13

Dhudshia, Bhartesh, and Avinash N. Thadani. "Acyclic diaminocarbenes: simple, versatile ligands for cross-coupling reactions." Chemical Communications, no. 6 (2006): 668. http://dx.doi.org/10.1039/b516398f.

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14

Siemeling, Ulrich. "Yes They Can: Small-molecule Activation with Stable Diaminocarbenes." Australian Journal of Chemistry 64, no. 8 (2011): 1109. http://dx.doi.org/10.1071/ch11244.

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Although small-molecule activation has long been the exclusive domain of transition metal chemistry, it has been increasingly realized that subvalent heavier main-group element compounds, too, are capable of activating H2, NH3, CO, etc. In a remarkable breakthrough, it was recently discovered that this is even possible with certain selected carbon(ii) compounds, viz. (alkyl)(amino)carbenes. However, N-heterocyclic carbenes and related diaminocarbenes, which represent the largest and most widely applied class of singlet carbenes, have been judged to be incapable of exhibiting similar reactivity. It now turns out that this is not quite true and that their reactivity needs to be reassessed.

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15

Snead, David R., Ion Ghiviriga, Khalil A. Abboud, and Sukwon Hong. "A New Route to Acyclic Diaminocarbenes via Lithium−Halogen Exchange." Organic Letters 11, no. 15 (August 6, 2009): 3274–77. http://dx.doi.org/10.1021/ol9013156.

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16

Lehmann, John F., Stephen G. Urquhart, Laura E. Ennis, Adam P. Hitchcock, Ken Hatano, Shilpi Gupta, and Michael K. Denk. "Core Excitation Spectroscopy of Stable Cyclic Diaminocarbenes, -silylenes, and -germylenes." Organometallics 18, no. 10 (May 1999): 1862–72. http://dx.doi.org/10.1021/om980882z.

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17

Marchenko, Anatoliy, Georgyi Koidan, Anastasiya Hurieva, Yurii Vlasenko, Alexander B. Rozhenko, Jean-Marc Sotiropoulos, and Aleksandr Kostyuk. "Transformation Routes of PV - and PIII -N -Substituted Acyclic Diaminocarbenes." European Journal of Inorganic Chemistry 2019, no. 11-12 (December 12, 2018): 1621–32. http://dx.doi.org/10.1002/ejic.201801141.

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18

Melaimi, Mohand, Michele Soleilhavoup, and Guy Bertrand. "ChemInform Abstract: Stable Cyclic Carbenes and Related Species Beyond Diaminocarbenes." ChemInform 42, no. 8 (January 27, 2011): no. http://dx.doi.org/10.1002/chin.201108261.

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19

Hahn, F. Ekkehardt, Martin Paas, Duc Le Van, and Roland Fröhlich. "Spirocyclic Diaminocarbenes: Synthesis, Coordination Chemistry, and Investigation of Their Dimerization Behavior." Chemistry - A European Journal 11, no. 17 (August 19, 2005): 5080–85. http://dx.doi.org/10.1002/chem.200500306.

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20

Alder, Roger W., Leila Chaker, and Fran�ois P. V. Paolini. "Bis(diethylamino)carbene and the mechanism of dimerisation for simple diaminocarbenes." Chemical Communications, no. 19 (2004): 2172. http://dx.doi.org/10.1039/b409112d.

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21

Lai, Chin Hung. "A theoretical study on the hydrogen adducts of diamidocarbenes and diaminocarbenes." Journal of Molecular Modeling 19, no. 12 (November 19, 2013): 5523–32. http://dx.doi.org/10.1007/s00894-013-2052-0.

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22

Fehlhammer, Wolf Peter, Thomas Bliß, Joachim Fuchs, and Gerhard Holzmann. "Homoleptische Carbenkomplexe, IV. Tetrakis(N-alkylimidazolin-2-yliden)palladium and -platin/Homoleptic Carbene Complexes, IV. Tetrakis(N-alkylimidazolin-2-ylidene)palladium and -platinum." Zeitschrift für Naturforschung B 47, no. 1 (January 1, 1992): 79–89. http://dx.doi.org/10.1515/znb-1992-0116.

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Homoleptic complexes of palladium and platinum containing carbenoid imidazole ligands (1, 12-19 ) have been synthesized either directly from C2-lithiated N-methyl-imidazole and Pdl2 or, indirectly (and more efficiently), from isocyanides and 2-am inoacetaldehyde diethylacetale in the presence of Pdl2, Ptl2 or K2PtCl4 via the respective “ open chain” diaminocarbenes 2-11. Selected IR , NMR (1H , 13C), and pos-FAB mass spectrometric data of the new compounds are reported. The X-ray structure analysis of tetrakis(N -methylimidazolin-2-ylidene)palladium-diiodide (lb ) reveals a geometry of the heterocyclic ligands which deviates considerably from the one expected for extensive 6π-electron delocalization across the ring.

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23

Aliaga-Lavrijsen, Mélanie, Raquel P. Herrera, M. Dolores Villacampa, and M. Concepción Gimeno. "Efficient Gold(I) Acyclic Diaminocarbenes for the Synthesis of Propargylamines and Indolizines." ACS Omega 3, no. 8 (August 23, 2018): 9805–13. http://dx.doi.org/10.1021/acsomega.8b01352.

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24

Snead, David R., Ion Ghiviriga, Khalil A. Abboud, and Sukwon Hong. "ChemInform Abstract: A New Route to Acyclic Diaminocarbenes via Lithium-Halogen Exchange." ChemInform 40, no. 48 (November 6, 2009): no. http://dx.doi.org/10.1002/chin.200948099.

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25

Pytkowicz, Julien, Sylvain Roland, and Pierre Mangeney. "Enantioselective conjugate addition of diethylzinc using catalytic silver(I) diaminocarbenes and Cu(OTf)2." Tetrahedron: Asymmetry 12, no. 15 (August 2001): 2087–89. http://dx.doi.org/10.1016/s0957-4166(01)00325-1.

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26

Dastgir, Sarim, Karl S. Coleman, Andrew R. Cowley, and Malcolm L. H. Green. "Stable crystalline annulated diaminocarbenes: coordination with rhodium(i), iridium(i) and catalytic hydroformylation studies." Dalton Transactions, no. 35 (2009): 7203. http://dx.doi.org/10.1039/b905729c.

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27

Herrmann, Wolfgang A., Karl Öfele, Denise v. Preysing, and Eberhardt Herdtweck. "Metal complexes of acyclic diaminocarbenes: links between N-heterocyclic carbene (NHC)- and Fischer-carbene complexes." Journal of Organometallic Chemistry 684, no. 1-2 (November 2003): 235–48. http://dx.doi.org/10.1016/s0022-328x(03)00754-x.

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28

Otto, Michael, Salvador Conejero, Yves Canac, Vadim D. Romanenko, Valentyn Rudzevitch, and Guy Bertrand. "Mono- and Diaminocarbenes from Chloroiminium and -amidinium Salts: Synthesis of Metal-Free Bis(dimethylamino)carbene." Journal of the American Chemical Society 126, no. 4 (February 2004): 1016–17. http://dx.doi.org/10.1021/ja0393325.

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29

Jonek, Markus, Hannes Buhl, Michael Leibold, Clemens Bruhn, and Ulrich Siemeling. "Evaluation of benzthiazolidine-based formamidinium salts for the synthesis of penem-type β-lactams by uncatalysed carbonylation of acyclic diaminocarbenes." Zeitschrift für Naturforschung B 74, no. 4 (April 24, 2019): 365–72. http://dx.doi.org/10.1515/znb-2019-0017.

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AbstractThe reaction of [iPr2N=CHCl]Cl with 2-phenylbenzthiazolidine (Ph-BtzH) and subsequent anion metathesis afforded the formamidinium salt [(Ph-Btz)CH(NiPr2)][PF6] ([1aH][PF6]). The reaction of [1aH][PF6] with (Me3Si)2NNa in the presence of grey selenium furnished the selenourea derivative 1aSe as trapping product of the acyclic diaminocarbene 1a. In the absence of selenium, a 2H-1,4-benzothiazine derivative (2) was obtained, which is an isomer of 1a, whose formation is plausibly initiated by deprotonation of [1aH]+ not at the cationic N2CH unit, but at the neighbouring PhCH position. CO was ineffective as trapping reagent for 1a. [1aH][PF6], 1aSe and 2 have been structurally characterised by X-ray diffraction.

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30

Kassaee, M. Z., N. Khorshidvand, A. A. Ahmadi, and P. T. Cummings. "Steric effects on normal and abnormal acyclic, cyclic-saturated, and cyclic-unsaturated diaminocarbenes using DFT method." Journal of Physical Organic Chemistry 32, no. 2 (October 10, 2018): e3898. http://dx.doi.org/10.1002/poc.3898.

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31

Pytkowicz, Julien, Sylvain Roland, and Pierre Mangeney. "ChemInform Abstract: Enantioselective Conjugate Addition of Diethylzinc Using Catalytic Silver(I) Diaminocarbenes and Cu(OTf)2." ChemInform 33, no. 7 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200207035.

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32

Marchenko, Anatoliy, Georgyi Koidan, Anastasiya Hurieva, Yurii Vlasenko, Aleksandr Kostyuk, and Andrea Biffis. "Palladium(ii) complexes with chelating N-phosphanyl acyclic diaminocarbenes: synthesis, characterization and catalytic performance in Suzuki couplings." Dalton Transactions 45, no. 5 (2016): 1967–75. http://dx.doi.org/10.1039/c5dt02250a.

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33

Montanel-Pérez, Sara, Anabel Izaga, Antonio Laguna, M. Dolores Villacampa, and M. Concepción Gimeno. "Synthesis of Gold(III) Complexes with Bidentate Amino-Thiolate Ligands as Precursors of Novel Bifunctional Acyclic Diaminocarbenes." ACS Omega 3, no. 10 (October 11, 2018): 13097–103. http://dx.doi.org/10.1021/acsomega.8b01547.

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34

Owusu, Millicent O., Sachin Handa, and LeGrande M. Slaughter. "Chugaev-type bis(acyclic diaminocarbenes) as a new ligand class for the palladium-catalyzed Mizoroki-Heck reaction." Applied Organometallic Chemistry 26, no. 12 (October 3, 2012): 712–17. http://dx.doi.org/10.1002/aoc.2915.

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35

Shi, Yao-Cheng, Shuai Wang, and Sun Xie. "Syntheses, molecular structures, and self-assemblies of SFe3, S2Fe3, S3Fe5, SeFe3, and Se2Fe3 clusters with chelating diaminocarbenes." Journal of Coordination Chemistry 68, no. 21 (September 23, 2015): 3852–83. http://dx.doi.org/10.1080/00958972.2015.1079312.

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36

Alder, Roger W., Michael E. Blake, and Josep M. Oliva. "Diaminocarbenes; Calculation of Barriers to Rotation about Ccarbene−N Bonds, Barriers to Dimerization, Proton Affinities, and13C NMR Shifts." Journal of Physical Chemistry A 103, no. 50 (December 1999): 11200–11211. http://dx.doi.org/10.1021/jp9934228.

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37

Boyarskiy, Vadim P., Konstantin V. Luzyanin, and Vadim Yu Kukushkin. "Acyclic diaminocarbenes (ADCs) as a promising alternative to N-heterocyclic carbenes (NHCs) in transition metal catalyzed organic transformations." Coordination Chemistry Reviews 256, no. 17-18 (September 2012): 2029–56. http://dx.doi.org/10.1016/j.ccr.2012.04.022.

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38

Wallbaum, Lars, Daniel Weismann, Dennis Löber, Clemens Bruhn, Pascal Prochnow, Julia E. Bandow, and Ulrich Siemeling. "Stable and Persistent Acyclic Diaminocarbenes with Cycloalkyl Substituents and Their Transformation to β-Lactams by Uncatalysed Carbonylation with CO." Chemistry - A European Journal 25, no. 6 (December 27, 2018): 1488–97. http://dx.doi.org/10.1002/chem.201805307.

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39

Owusu, Millicent O., Sachin Handa, and LeGrande M. Slaughter. "ChemInform Abstract: Chugaev-Type Bis(acyclic diaminocarbenes) as a New Ligand Class for the Palladium-Catalyzed Mizoroki-Heck Reaction." ChemInform 44, no. 19 (April 18, 2013): no. http://dx.doi.org/10.1002/chin.201319086.

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40

Dzhevakov, P. B., A. F. Asachenko, A. N. Kashin, I. P. Beletskaya, and M. S. Nechaev. "Catalytic activity of palladium complexes with stable diaminocarbenes containing five-, six- and seven-membered rings in the Suzuki-Miyaura reaction." Russian Chemical Bulletin 63, no. 4 (April 2014): 890–94. http://dx.doi.org/10.1007/s11172-014-0525-7.

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41

Wallbaum, Lars, Daniel Weismann, Dennis Löber, Clemens Bruhn, Pascal Prochnow, Julia E. Bandow, and Ulrich Siemeling. "Cover Feature: Stable and Persistent Acyclic Diaminocarbenes with Cycloalkyl Substituents and Their Transformation to β-Lactams by Uncatalysed Carbonylation with CO (Chem. Eur. J. 6/2019)." Chemistry - A European Journal 25, no. 6 (January 16, 2019): 1364. http://dx.doi.org/10.1002/chem.201806283.

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42

Dastgir, Sarim, Karl S. Coleman, Andrew R. Cowley, and Malcolm L. H. Green. "Synthesis, Structure, and Temperature-Dependent Dynamics of Neutral Palladium Allyl Complexes of Annulated Diaminocarbenes and Their Catalytic Application for C−C and C−N Bond Formation Reactions†." Organometallics 29, no. 21 (November 8, 2010): 4858–70. http://dx.doi.org/10.1021/om1000327.

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43

Arduengo, Anthony J., Jens R. Goerlich, and William J. Marshall. "A stable diaminocarbene." Journal of the American Chemical Society 117, no. 44 (November 1995): 11027–28. http://dx.doi.org/10.1021/ja00149a034.

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44

Gee, Jack C., Beth A. Fuller, Hannah-Marie Lockett, Gita Sedghi, Craig M. Robertson, and Konstantin V. Luzyanin. "Visible light accelerated hydrosilylation of alkynes using platinum–[acyclic diaminocarbene] photocatalysts." Chemical Communications 54, no. 68 (2018): 9450–53. http://dx.doi.org/10.1039/c8cc04287j.

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45

César, Vincent, Valentina Mallardo, Adela Nano, Georges Dahm, Noël Lugan, Guy Lavigne, and Stéphane Bellemin-Laponnaz. "IMes-acac: hybrid combination of diaminocarbene and acetylacetonato sub-units into a new anionic ambidentate NHC ligand." Chemical Communications 51, no. 25 (2015): 5271–74. http://dx.doi.org/10.1039/c4cc08641d.

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46

Anisimova, Tatyana B., Mikhail A. Kinzhalov, M. Fátima C. Guedes da Silva, Alexander S. Novikov, Vadim Yu Kukushkin, Armando J. L. Pombeiro, and Konstantin V. Luzyanin. "Addition of N-nucleophiles to gold(iii)-bound isocyanides leading to short-lived gold(iii) acyclic diaminocarbene complexes." New Journal of Chemistry 41, no. 9 (2017): 3246–50. http://dx.doi.org/10.1039/c7nj00529f.

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47

Ruiz, Javier, Lucía García, Marilín Vivanco, Daniel Sol, and Santiago García-Granda. "Half-sandwich iron(ii) complexes with protic acyclic diaminocarbene ligands: synthesis, deprotonation and metalation reactions." Dalton Transactions 46, no. 31 (2017): 10387–98. http://dx.doi.org/10.1039/c7dt02049j.

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48

Kinzhalov, Mikhail A., Anzhelika A. Eremina, Andrey S. Smirnov, Vitalii V. Suslonov, Vadim Yu Kukushkin, and Konstantin V. Luzyanin. "Cleavage of acyclic diaminocarbene ligands at an iridium(iii) center. Recognition of a new reactivity mode for carbene ligands." Dalton Transactions 48, no. 22 (2019): 7571–82. http://dx.doi.org/10.1039/c9dt01138b.

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49

Martínez-Junquera, Mónica, Elena Lalinde, M. Teresa Moreno, Elvira Alfaro-Arnedo, Icíar P. López, Ignacio M. Larráyoz, and José G. Pichel. "Luminescent cyclometalated platinum(ii) complexes with acyclic diaminocarbene ligands: structural, photophysical and biological properties." Dalton Transactions 50, no. 13 (2021): 4539–54. http://dx.doi.org/10.1039/d1dt00480h.

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We report new cyclometalated Pt(ii) complexes bearing acyclic diaminocarbene (ADC) ligands, which feature competitive phosphorescence quantum yields, aggregation induced emission and cytotoxic activity towards tumor cell lines.

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50

Maiti, Avijit, Shubhadeep Chandra, Biprajit Sarkar, and Anukul Jana. "Acyclic diaminocarbene-based Thiele, Chichibabin, and Müller hydrocarbons." Chemical Science 11, no. 43 (2020): 11827–33. http://dx.doi.org/10.1039/d0sc03622f.

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We report the synthesis of acyclic diaminocarbene (ADC)-scaffold based Thiele, Chichibabin, and Müller hydrocarbons. Studies support that the singlet-triplet energy gap depends on the π-conjugated spacer between the ADC scaffolds.

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