Recent advancements in Ni/photoredox dual catalysis for the Csp3-Csp3 cross-coupling reactions DOI Creative Commons

Qi-Yun Huang,

Min Shi

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(17), P. 4913 - 4925

Published: Jan. 1, 2024

This minireview highlights recent advancements in the past five years (since 2019) Ni/photoredox dual catalysis for Csp 3 –Csp cross-coupling reactions.

Language: Английский

The Multiple Roles of Bipyridine-Nickel(II) Complex in Versatile Photoredox C(sp2)–C(sp3) Cross-Coupling DOI
Jingsheng Li,

Tengfei Kang,

Xiao Yi

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3328 - 3338

Published: Feb. 9, 2025

Language: Английский

Citations

1
Triply Selective & Sequential Diversification at Csp3: Expansion of Alkyl Germane Reactivity for C−C & C−Heteroatom Bond Formation DOI Creative Commons

Eric Ahrweiler,

Markus D. Schoetz,

Gurdeep Singh

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(16)

Published: Feb. 22, 2024

Abstract We report the triply selective and sequential diversification of a single C sp 3 carbon carrying Cl, Bpin GeEt for modular programmable construction ‐rich molecules. Various functionalizations −Cl −BPin (e.g. alkylation, arylation, homologation, amination, hydroxylation) were tolerated by −GeEt group. Moreover, methodological repertoire alkyl germane functionalization was significantly expanded beyond hitherto known Giese addition arylation to alkynylation, alkenylation, cyanation, halogenation, azidation, C−S bond formation as well first demonstration stereo‐selective ‐[Ge] bond.

Language: Английский

Citations

6
Palladium-catalyzed Suzuki-Miyaura cross-couplings of stable glycal boronates for robust synthesis of C-1 glycals DOI Creative Commons

Anrong Chen,

Zhi Yang,

Rongfeng Wu

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: June 19, 2024

Abstract C- 1 Glycals serve as pivotal intermediates in synthesizing diverse C -glycosyl compounds and natural products, necessitating the development of concise, efficient user-friendly methods to obtain glycosides is essential. The Suzuki-Miyaura cross-coupling glycal boronates notable for its reliability non-toxic nature, but donor stability remains a challenge. Herein, we achieve significant breakthrough by developing stable boronates, effectively overcoming issue glycal-based Suzuki–Miyaura coupling. Leveraging balanced reactivity our establish robust palladium-catalyzed reaction, facilitating formation various C( sp 2 )-C( ), 3 ) bonds under mild conditions. Notably, expand upon this achievement DNA-compatible reaction synthesize glycal-DNA conjugates. With excellent reactivity, stability, generality, ease handling, method holds promise widespread appication preparation products.

Language: Английский

Citations

6
Unlocking the Reactivity of the C-In Bond: Alkyl Indium Reagents as a Source of Radicals Under Photocatalytic Conditions DOI Creative Commons
Anton A. Gladkov, Vitalij V. Levin,

Demian Y. Cheboksarov

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Generation of organic radicals from organometallic compounds is a key step in metallaphotoredox cross-coupling reactions. The ability organoindium to serve as sources alkyl under light promoted oxidative conditions described. Organoindium reagents were used dual photocatalytic/nickel with aryl bromides. These can be conveniently obtained primary, secondary and tertiary bromides chlorides using novel indium(i) bromide/lithium bromide system. Both steps, the formation organoindiums their are insensitive towards air moisture tolerate wide variety functional groups.

Language: Английский

Citations

0
Fundamentals of Photoluminescent Materials DOI
Ahmed Olalekan Omoniyi, Adefarati Oloruntoba,

Jamilu Tijjani Baraya

et al.

Engineering materials, Journal Year: 2025, Volume and Issue: unknown, P. 17 - 64

Published: Jan. 1, 2025

Language: Английский

Citations

0
Direct construction of aryl amide N-glycosides from glycosyl oxamic acids via photoredox palladium-catalyzed aminocarbonylations DOI

Xinyue Xie,

Shiyin Zhao, Zhi Yang

et al.

Chem Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 101109 - 101109

Published: Sept. 1, 2024

Language: Английский

Citations

3
Photoredox Activation of Fluorinated Organozinc Reagents: Hydrofluoroalkylation of Unactivated and Electron Deficient Alkenes DOI
Anton A. Gladkov, Vitalij V. Levin, Alexander D. Dilman

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11826 - 11835

Published: July 26, 2024

Hydrofluoroalkylation of alkenes with organozinc reagents under photocatalytic conditions is described. The fluorinated alkyl radicals were generated from organozincs by the single electron oxidation carbon-zinc bond. radical addition step followed either hydrogen atom transfer for unactivated olefins or a reduction/protonation sequence strongly accepting arylidenemalononitriles.

Language: Английский

Citations

1
Amphiphilic Fluorescein Triazoles: Synthesis and Visible Light Catalysis in Water DOI Open Access
Alina А. Аrtemenko, Elza D. Sultanova, Diana Mironova

et al.

Published: July 25, 2024

Triazole derivatives of fluorescein containing N,N-dimethylaminopropyl fragments and their ammonium salts were synthesized with yields 74 - 85%. The resulting compounds exhibit fluorescent properties in the green region visible spectrum. critical aggregation concentration (CAC) was estimated using a py-rene probe corresponding to range 0.28 1.43 mM, at concentrations above CAC form stable aggregates ranging from 165 202 nm. A relative quantum yield 5-24% has been calculated based on fluorescence UV spectra. best value is shown by derivative tetradecyl substituent. When studying photocatalytic through reaction between N-substituted 1,2,3,4-tetrahydroisoquinoline malonic ester, mono-tetradecyl deriva-tive demonstrated results. According gas chromatography-mass spectrometry (GC-MS) data, conversion initial heterocycle reached 95%. Therefore, these have potential act as an effective photocatalysts.

Language: Английский

Citations

1
Amphiphilic Fluorescein Triazoles: Synthesis and Visible-Light Catalysis in Water DOI Creative Commons
Alina А. Аrtemenko, Elza D. Sultanova, Diana Mironova

et al.

Organics, Journal Year: 2024, Volume and Issue: 5(3), P. 346 - 360

Published: Sept. 11, 2024

Triazole derivatives of fluorescein-containing N,N-dimethylaminopropyl fragments and their ammonium salts were synthesized with yields 74–85%. The resulting compounds exhibit fluorescent properties in the green region visible spectrum. critical aggregation concentration (CAC) was estimated using a pyrene probe corresponding to range 0.28–1.43 mM, at concentrations above CAC, form stable aggregates ranging from 165 202 nm. A relative quantum yield 5–24% has been calculated based on fluorescence UV spectra. best value is shown by derivative containing tetradecyl substituent. When studying photocatalytic through reaction between N-substituted 1,2,3,4-tetrahydroisoquinoline malonic ester, mono-tetradecyl demonstrated results. According gas chromatography–mass spectrometry (GC-MS) data, conversion initial heterocycle reached 95%. Therefore, these have potential act as an effective photocatalysts.

Language: Английский

Citations

1
Artificial Intelligence-Driven Development of Nickel-Catalyzed Enantioselective Cross-Coupling Reactions DOI
Yadong Gao,

Kunjun Hu,

Jianhang Rao

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 18457 - 18468

Published: Dec. 3, 2024

The conventional approach to developing asymmetric synthetic methods relies heavily on empirical optimization. However, the integration of artificial intelligence (AI) and high-throughput experimentation (HTE) technology presents a paradigm shift with immense potential revolutionize discovery optimization reactions. In this study, we present an efficient workflow for development series nickel-catalyzed cross-coupling reactions, leveraging AI HTE technology. Many enantioselective reactions share common Ni(III) intermediate, which dictates enantioselectivity. To harness mechanistic insight, embarked predictive model coupling elucidating general rules governing Through application data science tools technology, curated set construct AI-based model. This was subsequently utilized facilitate nickel hydride-catalyzed regioselective Employing AI-assisted virtual ligand screening HTE-enabled condition optimization, successfully identified optimal ligands eight Consequently, chiral sp3 C–C bonds were synthesized high yield

Language: Английский

Citations

1