Advances and Prospects in Understanding London Dispersion Interactions in Molecular Chemistry DOI Creative Commons
Lars Rummel, Peter R. Schreiner

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(12)

Published: Dec. 5, 2023

Abstract London dispersion (LD) interactions are the main contribution of attractive part van der Waals potential. Even though LD effects driving force for molecular aggregation and recognition, role these omnipresent in structure reactivity had been largely underappreciated over decades. However, recent years considerable efforts have made to thoroughly study their potential as a chemical design element structures catalysis. This was possible through fruitful interplay theory experiment. review highlights results advances utilizing structural motif understand utilize intra‐ intermolecularly LD‐stabilized systems. Additionally, we focus on quantification fundamental reactions.

Language: Английский

Recent developments in enantio- and diastereoselective hydrogenation of N-heteroaromatic compounds DOI Creative Commons
Gunasekar Ramachandran, Ross L. Goodyear, Ilaria Proietti Silvestri

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(9), P. 1794 - 1827

Published: Jan. 1, 2022

The enantioselective and diastereoselective hydrogenation of N-heteroaromatic compounds is an efficient strategy to access chirally enriched cyclic heterocycles, which often possess highly bio-active properties. This strategy, however, has only been established in recent times. part due the challenges high stability aromatic presence heteroatoms that have potential poison chiral catalysts. Additionally, are a structurally diverse family substrates, each group showing distinct reactivity hydrogenation. Advances years allowed various compounds, including pyridines, indoles, quinolines, isoquinolines, quinoxalines imidazoles, be hydrogenated with good excellent enantioselectivity under appropriate reaction conditions. Transition-metal catalysis, utilising iridium, ruthenium, rhodium, palladium complexes, found play important role this field. More recently, organocatalysis shown for certain compounds. review provides analysis developments importance these molecules their applications drug discovery highlighted throughout review.

Language: Английский

Citations

59

Advances and Prospects in Understanding London Dispersion Interactions in Molecular Chemistry DOI Creative Commons
Lars Rummel, Peter R. Schreiner

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(12)

Published: Dec. 5, 2023

London dispersion (LD) interactions are the main contribution of attractive part van der Waals potential. Even though LD effects driving force for molecular aggregation and recognition, role these omnipresent in structure reactivity had been largely underappreciated over decades. However, recent years considerable efforts have made to thoroughly study their potential as a chemical design element structures catalysis. This was possible through fruitful interplay theory experiment. review highlights results advances utilizing structural motif understand utilize intra- intermolecularly LD-stabilized systems. Additionally, we focus on quantification fundamental reactions.

Language: Английский

Citations

30

Unsymmetrically N, S-coordinated single-atom cobalt with electron redistribution for catalytic hydrogenation of quinolines DOI
Feiying Tang, Guangji Zhang, Liqiang Wang

et al.

Journal of Catalysis, Journal Year: 2022, Volume and Issue: 414, P. 101 - 108

Published: Sept. 5, 2022

Language: Английский

Citations

32

Ruthenium-Catalyzed Carbocycle-Selective Hydrogenation of Fused Heteroarenes DOI Creative Commons

Chenguang Luo,

Chao Wu, Xiaoming Wang

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 11, 2024

The homogeneous catalytic hydrogenation of benzo-fused heteroarenes generally provides partially hydrogenated products wherein the heteroaryl ring is preferentially reduced, such as quinoline hydrogenation, leading to 1,2,3,4-tetrahydroquinoline. Herein, we report a carbocycle-selective fused

Language: Английский

Citations

6

Development of a General and Selective Nanostructured Cobalt Catalyst for the Hydrogenation of Benzofurans, Indoles and Benzothiophenes DOI Creative Commons
Bei Zhou, Vishwas G. Chandrashekhar, Zhuang Ma

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(10)

Published: Jan. 13, 2023

The selective hydrogenation of benzofurans in the presence a heterogeneous non-noble metal catalyst is reported. developed optimal catalytic material consists cobalt-cobalt oxide core-shell nanoparticles supported on silica, which has been prepared by immobilization and pyrolysis cobalt-DABCO-citric acid complex silica under argon at 800 °C. This novel allows for simple functionalized to 2,3-dihydrobenzofurans as well related heterocycles. versatility reported protocol showcased reduction selected drugs deuteration Further, stability, recycling, reusability Co-nanocatalyst are demonstrated.

Language: Английский

Citations

16

The d-p electron coupling over the unsaturated oxygen coordinated CuCo alloy surface for enhanced N-heteroarenes hydrogenation under mild conditions DOI

Dengqi Zhou,

Ke Zeng, Liqiang Wang

et al.

Journal of Energy Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 1, 2025

Language: Английский

Citations

0

Atomically Dispersed Palladium Catalyst for Chemoselective Hydrogenation of Quinolines DOI

Shunwu Wang,

Zhenbo Guo,

Ligang Wang

et al.

Nano Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 23, 2024

Chemoselective hydrogenation of quinoline and its derivatives is a significant strategy to achieve the corresponding 1,2,3,4-tetrahydroquinolines (py-THQ) for various potential applications. Here, we precisely constructed titanium carbide supported atomically dispersed Pd catalyst (Pd

Language: Английский

Citations

3

Identification of Cyclohexadienyl Hydrides as Intermediates in Molybdenum‐Catalyzed Arene Hydrogenation DOI
Gabriele Hierlmeier,

Paolo Tosatti,

Kurt Puentener

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(3)

Published: Nov. 9, 2022

Treatment of phosphino(imino)pyridine (PIP) molybdenum cyclooctadiene (COD) complexes [(PIP)Mo(COD)] with dihydrogen in the presence benzene selectively furnished cyclohexadienyl hydrides [(PIP)MoH(η5 -C6 H7 )], which are precatalysts for hydrogenation to cyclohexane. )] arises from a rarely observed insertion into molybdenum-hydride bond, key step molybdenum-catalyzed homogeneous arenes. The reaction toluene afforded single isomer corresponding hydride while para-xylene predominantly formed η6 -arene complex product being minor component. Addition carbon monoxide cyclohexane-d12 solution liberated cyclohexadiene, providing experimental support higher kinetic barrier subsequent steps en route cycloalkanes.

Language: Английский

Citations

11

A Highly Active Cobalt Catalyst for the General and Selective Hydrogenation of Aromatic Heterocycles DOI Creative Commons
Christof Bauer,

Felix Müller,

Sercan Keskin

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(30)

Published: Feb. 24, 2023

Nanostructured earth abundant metal catalysts that mediate important chemical reactions with high efficiency and selectivity are of great interest. This study introduces a synthesis protocol for nanostructured catalysts. Three components, an inexpensive precursor, easy to synthesize N/C porous support material undergo pyrolysis give the catalyst in simple, single step. By applying this synthesis, highly active cobalt general selective hydrogenation aromatic heterocycles could be generated. The reaction is regard organic hydrogen storage. mild conditions observed quinolines permit numerous classes N-, O- S-heterocyclic compounds such as: quinoxalines, pyridines, pyrroles, indoles, isoquinoline, aciridine amine, phenanthroline, benzofuranes, benzothiophenes.

Language: Английский

Citations

5

Scalable Synthesis of ABBV-105 Enabled by Suzuki Coupling with Low Pd Loading, Ru-Catalyzed Asymmetric Hydrogenation, and Acylation Using Impinging Jet DOI
Benoit Cardinal‐David, Shashank Shekhar, Eric M. Phillips

et al.

Organic Process Research & Development, Journal Year: 2024, Volume and Issue: 28(8), P. 3229 - 3247

Published: July 17, 2024

Evolution of a synthetic process to prepare ABBV-105, Bruton's tyrosine kinase (BTK)-inhibitor, on multikilogram scale is described. The first-generation route utilized chiral resolution the penultimate intermediate (7). Either Bartoli or Leimgruber–Batcho indole synthesis was used key intermediate, boronate ester (23). As demand for API increased, found be low-yielding and expensive. It required column chromatography, had multiple alerting structures from mutagenic impurity assessment, suffered lack robustness. In second-generation novel Ru-catalyzed asymmetric hydrogenation 1,2,5,6-tetrahydropyridine (21) developed establish stereocenter. Compound 21 accessed via Suzuki coupling 23, prepared by Friedel–Crafts acylation, with vinyl bromide (24) in presence very low loading Pd catalyst (0.15 mol % Pd). Finally, (7) coupled acryloyl chloride using an impinging jet API. Detailed kinetic mechanistic work conducted control persistent impurities formed step. robust, chromatography-free high-yielding liability.

Language: Английский

Citations

1