Visible light-induced chemoselective 1,2-diheteroarylation of alkenes DOI Creative Commons

Shiyu Guo,

Yi-Peng Liu, Jingsong Huang

et al.

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

Published: July 19, 2024

Abstract Visible-light photocatalysis has evolved as a powerful technique to enable controllable radical reactions. Exploring unique photocatalytic mode for obtaining new chemoselectivity and product diversity is of great significance. Herein, we present photo-induced chemoselective 1,2-diheteroarylation unactivated alkenes utilizing halopyridines quinolines. The ring-fused azaarenes serve not only substrate, but also potential precursors halogen-atom abstraction pyridyl generation in this photocatalysis. As complement metal catalysis, process with mild redox neutral conditions assembles two different heteroaryl groups into regioselectively contribute broad substrates scope. obtained products containing aza-arene units permit various further diversifications, demonstrating the synthetic utility protocol. We anticipate that protocol will trigger advancement alkyl/aryl halides activation.

Language: Английский

Nickel‐Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp3)−C(sp3) Bonds Across Alkenes** DOI Creative Commons

Daniel M. Lux,

Vivek Aryal,

Doleshwar Niroula

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(32)

Published: June 15, 2023

We disclose a Ni-catalyzed regioselective dialkylation reaction of alkenylarenes with α-halocarbonyls and alkylzinc reagents. The produces γ-arylated alkanecarbonyl compounds the generation two new C(sp

Language: Английский

Citations

16

Iron-Catalyzed Regioselective Reductive Fluoroalkylalkenylation of Unactivated Alkenes DOI
Siyu Wang,

Bohao Guo,

Tong Mu

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(3), P. 1575 - 1583

Published: Jan. 16, 2024

The example of iron-catalyzed reductive fluoroalkylalkenylation unactivated alkenes has been disclosed, affording the stereodefined homoallylic fluoroalkanes with high efficiency and regioselectivity. This three-component cross-electrophile coupling features directing groups free, good functional group tolerance, broad substrate scope, late-stage difunctionalization biorelevant molecules. Moreover, this protocol sheds light on distinct reactivity disparities between fluoroalkyl nonfluoroalkyl radicals in cross-coupling reactions, highlighting unique nature iron/B2pin2 systems.

Language: Английский

Citations

5

Nickel-Catalyzed Reductive Alkene Cross-Dialkylation with Unactivated Alkyl Electrophiles DOI
Huixia Yang,

Z. ZHANG,

Panting Cao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(6), P. 1190 - 1195

Published: Feb. 3, 2024

A Ni-catalyzed reductive dialkylation of 8-aminoquinoline-tethered aliphatic alkenes with two unactivated alkyl electrophiles is disclosed here. Key to the development this transformation combination primary (pseudo)halides and secondary iodides that produce products in a single regioselective manner. The reaction exhibits good functional group compatibility, its synthetic utility was demonstrated by concise synthesis precursors biologically relevant molecules.

Language: Английский

Citations

5

Electron Deficient Ir–O Bonds Promote Heterogeneous Ir-Catalyzed Anti-Markovnikov Hydroboration of Alkenes under Mild Neat Conditions DOI
Shasha Zhang,

Xudong Zhao,

Yajun Qiu

et al.

Nano Letters, Journal Year: 2024, Volume and Issue: 24(17), P. 5165 - 5173

Published: April 17, 2024

Tuning electronic characteristics of metal–ligand bonds based on reaction pathways to achieve efficient catalytic processes has been widely studied and proven be feasible in homogeneous catalysis, but it is scarcely investigated heterogeneous catalysis. Herein, we demonstrate the regulation configuration Ir–O an Ir single-atom catalyst according borane activation mechanism. Ir1/Ni(OH)x are found more electron-poor than those Ir1/NiOx. Despite mild solvent-free conditions ambient temperature, exhibits outstanding performance for hydroboration alkenes, furnishing desired alkylboronic esters with a turnover frequency value ≤3060 h–1 99% anti-Markovnikov selectivity, which significantly better that Ir1/NiOx (42 h–1). It further as active centers oxidative so benefit H–B bond reductive pinacolborane.

Language: Английский

Citations

5

Visible light-induced chemoselective 1,2-diheteroarylation of alkenes DOI Creative Commons

Shiyu Guo,

Yi-Peng Liu, Jingsong Huang

et al.

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

Published: July 19, 2024

Abstract Visible-light photocatalysis has evolved as a powerful technique to enable controllable radical reactions. Exploring unique photocatalytic mode for obtaining new chemoselectivity and product diversity is of great significance. Herein, we present photo-induced chemoselective 1,2-diheteroarylation unactivated alkenes utilizing halopyridines quinolines. The ring-fused azaarenes serve not only substrate, but also potential precursors halogen-atom abstraction pyridyl generation in this photocatalysis. As complement metal catalysis, process with mild redox neutral conditions assembles two different heteroaryl groups into regioselectively contribute broad substrates scope. obtained products containing aza-arene units permit various further diversifications, demonstrating the synthetic utility protocol. We anticipate that protocol will trigger advancement alkyl/aryl halides activation.

Language: Английский

Citations

5