Elsevier eBooks, Journal Year: 2023, Volume and Issue: unknown, P. 442 - 465
Published: June 10, 2023
Language: Английский
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(6), P. 1858 - 1895
Published: Jan. 1, 2024
This review is planned to provide a comprehensive overview of the progress made in design and development chiral ligands for asymmetric gold catalysis.
Language: Английский
Citations
13
ACS Catalysis, Journal Year: 2025, Volume and Issue: 15(3), P. 2342 - 2350
Published: Jan. 24, 2025
The concise modular synthesis of a family monodentate 1,2-disubstituted ferrocene ligands containing diaryl phosphine and 2-aryl indole is described. Their gold(I) complexes were applied to the enantioselective gold(I)-catalyzed formal [4 + 2] cycloaddition 1,6-arylenynes, enyne cyclization/nucleophile addition N-tethered 1,6-enynes, methoxycyclization 1,6-arylenynes with high levels enantioselectivity in all cases. Crystallographic computational studies highlighted relevant role noncovalent interactions within ligand scaffold between substrate modes enantioinduction cyclization unsaturated substrates. Our recently developed open-source tool NEST was analyze chiral pockets catalysts, which combination RDKit allowed us understand these reactions, paving way for predictive-based approach toward rational development Au(I) catalysis.
Language: Английский
Citations
0
Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 28, 2025
The attractive force between two oppositely charged ions can constitute a powerful design tool in selective catalysis. Enzymes make extensive use of ionic interactions alongside variety other noncovalent interactions; recent years have seen synthetic chemists begin to seriously explore these catalyst designs that also incorporate reactive transition metal. In isolation, single interaction exhibits low directionality, but many successful systems they exist additional which provide high degree organization at the selectivity-determining state. Even situations with key interaction, directionality is not always detrimental, and even be advantageous, conferring generality catalyst. This Review explores approaches utilize control selectivity metal It divided into halves: first, occurs outer sphere complex, using ligand or bound an anion; second, bears formal charge, associated counterion.
Language: Английский
Citations
0
Chemistry - An Asian Journal, Journal Year: 2025, Volume and Issue: unknown
Published: April 28, 2025
Abstract Gold catalysis has witnessed remarkable advances over the past decade, with numerous insightful reviews chronicling this progress. However, a comprehensive review addressing developments in field during post‐pandemic COVID era remains notably absent. This aims to bridge that gap by providing an in‐depth analysis of recent studies, shedding light on unique properties gold complexes, particularly intriguing aurophilic interactions distinguish chemistry. The systematically explores latest achievements both mono‐ and dinuclear gold‐catalyzed reactions, focus their applications diverse fields, including redox coupling, asymmetric catalysis, photo‐, electrocatalysis. A special emphasis is placed comparative performance catalysts, latter often exhibiting enhanced catalytic efficiency selectivity certain reactions. By integrating mechanistic insights DFT perspectives representative experimental studies from years, highlights significance synthetic chemistry, identifies emerging trends outlines future directions for field.
Language: Английский
Citations
0
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(12), P. 2936 - 2942
Published: Jan. 1, 2023
.The TCDC approach enables tandem cycloisomerization/nucleophilic addition reactions of 2-alkynyl enones with naphthols, good to excellent control the regioselectivity and ees up 99%, under optimized reaction conditions.
Language: Английский
Citations
8
European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(38)
Published: June 23, 2022
H-bonded counterion-directed catalysis (HCDC) is a strategy wherein chiral anion that hydrogen-bonded to the achiral ligand of metal complex responsible for enantioinduction. In this article we present application Au(I)-catalyzed enantioselective tandem cycloisomerization-addition reaction 2-alkynyl enones. Following addition C-, N- or O-centered nucleophiles, bicyclic furans were obtained in moderate excellent yield and enantioselectivity (28 examples, 59-96 % yield, 62 : 38 95 5 er). The optimal catalytic system, comprising phosphinosquaramide Au(I) chloride BINOL-derived phosphoramidate Ag(I) salt, was selected combinatorial fashion from larger library with help high-throughput screening. An switch ca. 120 Δee% observed upon component salt.
Language: Английский
Citations
14
ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(15), P. 10217 - 10223
Published: July 20, 2023
The enantioselective reaction of 1,6-enynes with O-, N-, and C-nucleophiles has been developed by matched ion pair gold(I) catalysis in which the chiral cation anion are H-bonded through a urea group. Very high levels enantiocontrol achieved (up to >99:1 er) for broad scope substrates. DFT studies demonstrate importance H-bond donor group anchoring cation- anion-favoring additional noncovalent interactions.
Language: Английский
Citations
7
Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 621 - 627
Published: March 18, 2024
A polysubstituted 3-aminoimidazo[5,1- b ]oxazol-6-ium framework has been accessed from a new nitrenoid reagent by two-step ynamide annulation and imidazolium ring-formation sequence. Metalation with Au(I), Cu(I) Ir(I) at the C2 position provides an L-shaped NHC ligand scaffold that validated in gold-catalysed alkyne hydration arylative cyclisation reactions.
Language: Английский
Citations
2
Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(15), P. 3204 - 3226
Published: Aug. 5, 2024
Abstract Due to the presence of multiple reactive sites, including an alkyne, alkene, and a ketone, 2‐(1‐alkynyl)‐2‐alken‐1‐ones (yne‐enones) can successfully participate in synthesis various carbo‐, heterocycles, as well acyclic compounds. In this regard, wide variety transition metal catalysts organocatalysts are utilized cycloaddition functionalization reactions yne‐enones with other coupling partners. Considering versatility synthon, review, we have described metal‐catalyzed non‐metal‐catalyzed transformations over last decade.
Language: Английский
Citations
2
ACS Applied Polymer Materials, Journal Year: 2024, Volume and Issue: 6(5), P. 2453 - 2463
Published: Feb. 15, 2024
Two microporous polymer networks having a confined AuI carbene catalyst were obtained and tested for the skeletal rearrangement of enynes. These catalysts from precursor porous organic polymers (POPs), type network, synthesized by reaction isatin or mixture isatin/trifluoroacetophenone (1:1) with triptycene (POP1 POP2, respectively) through an electrophilic aromatic substitution, EAS, promoted trifluoromethanesulfonic acid. precursors could be easily functionalized lactam moiety to form (POP1-AuCarbene POP2-AuCarbene). The carbenes proved very active dimethyl 2-(3-methyl-2-butenyl)-2-propinylmalonate enyne. A large increase in stability was observed compared those most homogeneous described so far bibliography. This long-term associated separation atoms, induced their confinement networks. In particular, POP2-AuCarbene exhibited outstanding stability, maintaining catalytic activity even after several months.
Language: Английский
Citations
1