10228-82-7Relevant academic research and scientific papers
Triphenylene-based tris(N-heterocyclic carbene) ligand: Unexpected catalytic benefits
Gonell, Sergio,Poyatos, Macarena,Peris, Eduardo
, p. 7009 - 7013 (2013)
Triple play: A novel triphenylene-based tris(N-heterocyclic carbene) ligand with D3h symmetry and a highly π-delocalized system has been prepared and coordinated to palladium and gold (see figure). The catalytic activities of the new complexes
Dehydrogenation of aromatic amines to imines via ruthenium-catalyzed hydrogen transfer
Ell, Alida H.,Samec, Joseph S. M.,Brasse, Claudia,Baeckvall, Jan-E.
, p. 1144 - 1145 (2002)
An efficient ruthenium-catalyzed transfer dehydrogenation of amines to imines was achieved under mild conditions using 2,6-dimethoxy benzoquinone (2) or cat. 2/MnO2 as oxidant.
Gold catalysts with polyaromatic-NHC ligands. Enhancement of activity by addition of pyrene
Ibá?ez, Susana,Poyatos, Macarena,Peris, Eduardo
, p. 1447 - 1451 (2017)
Three Au(I) complexes with N-heterocyclic carbene ligands fused to polycyclic aromatic hydrocarbons (pyrene and phenanthrophenazine) have been obtained and fully characterized. The complexes were tested as catalysts in the hydroamination of terminal alkyn
Ruthenium N-Heterocyclic Carbene Complexes for Chemoselective Reduction of Imines and Reductive Amination of Aldehydes and Ketones
Kathuria, Lakshay,Samuelson, Ashoka G.
, (2020)
Chemoselective reduction of imines to secondary amines is catalyzed efficiently by tethered and untethered, half-sandwich ruthenium N-heterocyclic carbene (NHC) complexes at room temperature. The untethered Ru-NHC complexes are more efficient as catalysts for the reduction of aldimines and ketimines than the tethered complexes. Using the best untethered complex as a catalyst, electronic and steric demands on the reaction was probed using a series of imines. Chemoselectivity of the catalyst towards imine reduction was tested by performing inter and intramolecular competitive reactions in a variety of ways. The catalyst exhibits a very high TON and TOF under anaerobic conditions.
Synthesis and Catalytic Benefits of Tetranuclear Gold(I) Complexes with a C4-Symmetric Tetratriazol-5-ylidene
Flores-Jarillo, Mariana,Mendoza-Espinosa, Daniel,Salazar-Pereda, Verónica,González-Montiel, Simplicio
, p. 4305 - 4312 (2017)
The facile preparation of a C4-symmteric tetratriazolium salt and its subsequent metalation to generate a series of tetranuclear mesoionic carbene gold(I) complexes is presented. The complete structural characterization of the metallic carbenes
Regioselective mercury(I)/palladium(II)-catalyzed single-step approach for the synthesis of imines and 2-substituted indoles
Delgado, Francisco,Gutiérrez, Rsuini U.,Hernández-Montes, Mayra,Mendieta-Moctezuma, Aarón,Tamariz, Joaquín
, (2021/07/21)
An efficient synthesis of ketimines was achieved through a regioselective Hg(I)-catalyzed hydroamination of terminal acetylenes in the presence of anilines. The Pd(II)-catalyzed cycliza-tion of these imines into the 2-substituted indoles was satisfactorily carried out by a C-H acti-vation. In a single-step approach, a variety of 2-substituted indoles were also generated via a Hg(I)/Pd(II)-catalyzed, one-pot, two-step process, starting from anilines and terminal acetylenes. The arylacetylenes proved to be more effective than the alkyl derivatives.
Gold(I) complexes bearing ring-fused benzoxazine-derived triazolylidenes and their use in C–N bond-forming processes
Campos-Dominguez, Emmanuel,Vasquez-Perez, Jose,Rojas-Lima, Susana,Lopez-Ruiz, Heraclio,Mendoza-Espinosa, Daniel
, (2020/12/07)
We report the synthesis and full characterization of a novel series of ring-fused benzoxazine-derived triazolium salts (1a–c) and their corresponding triazolylidene gold(I) complexes (2a–c). All new compounds were fully characterized by means of 1H and 13C NMR spectroscopy, elemental analyses, and mass spectroscopy and in the case of triazoliums 1a and 1b by single-crystal X-ray diffraction. The new triazolylidene gold complexes (2a–c) were tested as precatalysts in the hydroamination and hydrohydrazination of terminal alkynes employing aniline derivatives and hydrazine as nitrogen sources, respectively.
Towards the rational design of ylide-substituted phosphines for gold(i)-catalysis: From inactive to ppm-level catalysis
Handelmann, Jens,Babu, Chatla Naga,Steinert, Henning,Schwarz, Christopher,Scherpf, Thorsten,Kroll, Alexander,Gessner, Viktoria H.
, p. 4329 - 4337 (2021/04/12)
The implementation of gold catalysis into large-scale processes suffers from the fact that most reactions still require high catalyst loadings to achieve efficient catalysis thus making upscaling impractical. Here, we report systematic studies on the impa
Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines
Kathuria, Lakshay,Samuelson, Ashoka G.
, (2020/12/28)
Enantioselective reduction of imines to the corresponding chiral secondary amines has been studied using a series of chiral half-sandwich iridium complexes. Chiral N-heterocyclic carbene (NHC) ligands in these complexes were synthesized from readily available, naturally occurring amino acids. Inexpensive phenylsilane was used as a convenient hydrogen donor. Under the optimized conditions, Ir-NHC complexes could reduce ketimines in good yields, albeit with moderate enantiomeric excess (ee). The phenylglycine derived chiral NHC was shown to give the best Ir catalyst and it also gave the maximum ee compared to catalysts prepared from other NHCs in this series. The opposite enantiomer of the reduction product was always obtained while using the Ir complex bearing a valine based NHC. The yields were consistently high with a variety of imine substrates having different steric and electronic demands.
Mono- and diylide-substituted phosphines (YPhos): Impact of the ligand properties on the catalytic activity in gold(i)-catalysed hydroaminations
Schwarz, Christopher,Handelmann, Jens,Baier, Daniel M.,Ouissa, Alina,Gessner, Viktoria H.
, p. 6808 - 6815 (2019/12/03)
Understanding the impact of ligand properties on their performance in catalysis is seminal for future ligand design and catalyst improvement. In this work, the influence of the steric and electronic properties on the efficiency of a series of mono- and di
