Journal of Catalysis, Journal Year: 2020, Volume and Issue: 383, P. 193 - 198
Published: Feb. 10, 2020
Language: Английский
Chemical Reviews, Journal Year: 2020, Volume and Issue: 120(4), P. 1981 - 2048
Published: Jan. 22, 2020
In this contribution, we provide a comprehensive overview of C-H activation methods promoted by NHC-transition metal complexes, covering the literature since 2002 (the year first report on metal-NHC-catalyzed activation) through June 2019, focusing both NHC ligands and methods. This review covers reactions catalyzed group 8 to 11 NHC-metal complexes. Through discussing role in promoting challenging methods, reader is provided with an important area its crucial forging carbon-carbon carbon-heteroatom bonds directly engaging ubiquitous bonds.
Language: Английский
Citations
542
Tetrahedron Letters, Journal Year: 2018, Volume and Issue: 60(4), P. 378 - 381
Published: Dec. 26, 2018
Language: Английский
Citations
96
Coordination Chemistry Reviews, Journal Year: 2020, Volume and Issue: 413, P. 213283 - 213283
Published: March 19, 2020
Language: Английский
Citations
87
Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 27(14), P. 4478 - 4499
Published: Sept. 29, 2020
The discovery of NHCs (NHC = N-heterocyclic carbenes) as ancillary ligands in transition-metal-catalysis ranks one the most important developments synthesis and catalysis. It is now well-recognized that strong σ-donating properties along with ease scaffold modification a steric shielding N-wingtip substituents around metal center enable dramatic improvements catalytic processes, including reactions are not possible using other ligands. In this context, although classical based on imidazolylidene imidazolinylidene ring systems well-established, recently tremendous progress has been made development applications BIAN-NHC (BIAN bis(imino)acenaphthene) class enhanced reactivity BIAN-NHCs direct result combination electronic collectively allow for major expansion scope processes can be accomplished NHCs. take advantage (1) stronger σ-donation, (2) lower lying LUMO orbitals, (3) presence an extended π-system, (4) rigid backbone pushes closer to by buttressing effect, thus resulting significantly improved control air-stability BIAN-NHC-metal complexes at low oxidation state. Acenaphthoquinone precursor enables facile modification, first time high yielding unsymmetrical unique properties. Overall, results highly attractive, easily accessible bring advances emerge leading practical alternative various aspects catalysis, cross-coupling C-H activation endeavors.
Language: Английский
Citations
71
Chemical Science, Journal Year: 2021, Volume and Issue: 12(31), P. 10583 - 10589
Published: Jan. 1, 2021
We report novel, sterically-bulky, easily-accessible NHC ligands based on the hash peralkylation concept. The new have been commercialized in collaboration with Millipore Sigma: IPr#HCl, 915653; Np#HCl; 915912; BIAN-IPr#HCl, 916420.
Language: Английский
Citations
68
Medicinal Research Reviews, Journal Year: 2024, Volume and Issue: 44(5), P. 2194 - 2235
Published: April 9, 2024
Abstract Metal complexes based on N ‐heterocyclic carbene (NHC) ligands have emerged as promising broad‐spectrum antitumor agents in bioorganometallic medicinal chemistry. In recent decades, studies cytotoxic metal–NHC yielded numerous compounds exhibiting superior cytotoxicity compared to cisplatin. Although the molecular mechanisms of these anticancer are not fully understood, some potential targets and modes action been identified. However, a comprehensive review their biological is currently absent. general, apoptosis caused by metal–NHCs common tumor cells. They can cause series changes after entering cells, such mitochondrial membrane (MMP) variation, reactive oxygen species (ROS) generation, cytochrome c (cyt c) release, endoplasmic reticulum (ER) stress, lysosome damage, caspase activation, ultimately leading apoptosis. Therefore, detailed understanding influence cancer cell crucial. this review, we provide summary advances that trigger apoptotic death via different apoptosis‐related or signaling pathways, including B‐cell lymphoma 2 (Bcl‐2 family), p53, cyt c, ER thioredoxin reductase (TrxR) inhibition, so forth. We also discuss challenges, limitations, future directions elucidate emerging application
Language: Английский
Citations
13
Organometallics, Journal Year: 2022, Volume and Issue: 41(16), P. 2281 - 2290
Published: Aug. 11, 2022
The first synthesis of Pd-PEPPSI N-heterocyclic carbene complexes derived from the abundant and renewable natural product caffeine is reported. catalysts bearing 3-chloro-pyridine, pyridine N-methylimidazole ancillary ligands were readily prepared corresponding N9-Me imidazolium salt by direct deprotonation coordination to PdX2 in presence N-heterocycles or ligand displacement PdX2(Het)2. model Pd-PEPPSI-caffeine complex has been characterized x-ray crystallography. successfully employed Suzuki cross-coupling aryl bromides, amides, Heck Sonogashira cross-coupling. Computational studies determine frontier molecular orbitals bond order analysis complexes. This class offers an entry utilize benign sustainable biomass-derived Xanthine NHC popular systems organic catalysis.
Language: Английский
Citations
25
Chemical Science, Journal Year: 2023, Volume and Issue: 14(19), P. 5141 - 5147
Published: Jan. 1, 2023
ItBu (ItBu = 1,3-di-tert-butylimidazol-2-ylidene) represents the most important and versatile N-alkyl N-heterocyclic carbene available in organic synthesis catalysis. Herein, we report synthesis, structural characterization catalytic activity of ItOct (ItOctyl), C2-symmetric, higher homologues ItBu. The new ligand class, including saturated imidazolin-2-ylidene analogues has been commercialized collaboration with MilliporeSigma: ItOct, 929 298; SItOct, 492 to enable broad access academic industrial researchers within field inorganic synthesis. We demonstrate that replacement t-Bu side chain t-Oct results highest steric volume carbenes reported date, while retaining electronic properties inherent N-aliphatic ligands, such as extremely strong σ-donation crucial reactivity carbenes. An efficient large-scale imidazolium imidazolinium SItOct precursors is presented. Coordination chemistry Au(i), Cu(i), Ag(i) Pd(ii) well beneficial effects on catalysis using complexes are described. Considering tremendous importance catalysis, metal stabilization, anticipate class ligands will find wide application pushing boundaries existing approaches
Language: Английский
Citations
13
Analytical Chemistry, Journal Year: 2024, Volume and Issue: 96(18), P. 7311 - 7320
Published: April 24, 2024
Human herpesvirus type 6A (HHV-6A) can cause a series of immune and neurological diseases, the establishment sensitive biosensor for rapid detection HHV-6A is great significance public health safety. Herein, bis-tridentate iridium complex (BisLT-Ir-NHC) comprising N-heterocyclic carbene (NHC) ligand as novel kind efficient ECL luminophore has been unprecedently reported. Based on its excellent properties, new ECL-based sandwich immunosensor to detect virus was successfully constructed by encapsulating BisLT-Ir-NHC into silica nanoparticles embellishing sensing interface with MXene@Au-CS. Notably, illustrated in this work not only had wide linear range 102 107 cps/μL but also showed outstanding recoveries (98.33–105.11%) real human serum an RSD 0.85–3.56%. Undoubtedly, these results demonstrated significant potential iridium(III) containing NHC developing analytical methods exploring kinds iridium-based luminophores future.
Language: Английский
Citations
5
ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(23), P. 14388 - 14394
Published: Nov. 15, 2021
A robust and scalable formal [4 + 3] annulation reaction for the synthesis of optically pure 1,4-benzodiazepinones 1,4-benzoxazepinones has been established by a combined catalytic system consisting chiral NHC, Ir/phosphine-olefin complex, an achiral urea, enabling asymmetric selective inhibitor mitochondrial F1F0 ATP hydrolase.
Language: Английский
Citations
32