Palladium catalyzed C(sp3)-H alkylation of 8-methylquinolines with aziridines: access to functionalized γ-quinolinylpropylamines DOI
Apurba Ranjan Sahoo, Tripti Paul, Shubhajit Basak

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(99), P. 14818 - 14821

Published: Jan. 1, 2024

An intrinsic directing group-assisted site-selective C(sp 3 )–H alkylation of 8-methylquinolines has been accomplished using readily available aziridines and Pd( ii ) catalysis.

Language: Английский

Nickel-Catalyzed Rearranged Alkenylation of 2-Arylaziridines with Aryl Alkenes to Access Allylamines DOI
Xiangkai Kong,

Ming-Bai Gou,

Bo Li

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

The transition-metal-catalyzed ring-opening functionalization of aziridines presents a promising approach for synthesizing structurally complex amines. However, the rearranged poses significant challenges. Herein, we report first alkenylation with aryl alkenes via Ni-Brønsted acid co-catalysis, leading to rapid synthesis diverse array allylamines yields reaching up 91%. Mechanistic studies suggest that reaction occurs through rearrangement aziridine generate an imine intermediate. This intermediate is subsequently captured by alkene under nickel catalysis, ultimately formation allylamines.

Language: Английский

Citations

1
Photoinduced nickel-catalysed enantioconvergent sp3–sp3 coupling of unactivated olefins and aziridines DOI
Liangliang Zhang, Hao Wang, Tomás G. Santiago

et al.

Nature Catalysis, Journal Year: 2025, Volume and Issue: unknown

Published: March 28, 2025

Language: Английский

Citations

1
Dynamic Kinetic Activation of Aziridines Enables Radical-Polar Crossover (4 + 3) Cycloaddition with 1,3-Dienes DOI
Lei Wang, Panpan Zhou, Dong Xie

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 10, 2025

The cycloaddition of aziridines with unsaturated compounds is a valuable method for synthesizing nitrogen heterocycles. However, this process predominantly substrate-controlled, posing significant challenges in regulating the regioselectivity C–N bond cleavage. In study, we report nickel-catalyzed dynamic kinetic activation strategy that enables catalyst-controlled aziridines. Various types aziridines, including 2-phenyl, 2-carbonyl, 2-alkyl, and disubstituted consistently cleave their more sterically hindered bonds to generate 1,3-radical anion intermediates. These intermediates participate highly regioselective 1,4-Heck/allylic substitution cascade aromatic branched 1,3-dienes, resulting radical-polar crossover (4 + 3) produces seven-membered azepine products. This approach not only complements traditional dipolar cycloaddition, which typically act as zwitterionic 1,3-dipoles, but also introduces an unusual mode 1,3-dienes. Experimental investigations density functional theory (DFT) calculations provide insight into reaction mechanism.

Language: Английский

Citations

0
Ni-catalyzed cross-electrophile alkyl-alkyl coupling reactions DOI Creative Commons

Li-Xu You,

Tian Lan,

Chunling Guo

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 3, 2025

Language: Английский

Citations

0
Illuminating enantioselective alkyl−alkyl coupling DOI

Weisai Zu,

Xin Luo, Haohua Huo

et al.

Nature Catalysis, Journal Year: 2025, Volume and Issue: 8(4), P. 289 - 290

Published: April 25, 2025

Language: Английский

Citations

0
Palladium catalyzed C(sp3)-H alkylation of 8-methylquinolines with aziridines: access to functionalized γ-quinolinylpropylamines DOI
Apurba Ranjan Sahoo, Tripti Paul, Shubhajit Basak

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(99), P. 14818 - 14821

Published: Jan. 1, 2024

An intrinsic directing group-assisted site-selective C(sp 3 )–H alkylation of 8-methylquinolines has been accomplished using readily available aziridines and Pd( ii ) catalysis.

Language: Английский

Citations

0