Cu-Catalyzed Synthesis of Symmetric Diarylamines from Organoboronic Acids Using NaNO2 as the Amino Source DOI
Daming Liu,

Hui You,

Shuo Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

A copper-catalyzed novel synthesis of symmetric diarylamines was achieved from aryl boronic acids and NaNO2. This protocol employs as the commercially available arylation reagents sodium nitrite (NaNO2) cheap, stable, solid amino source. Under a simple ligand- base-free copper catalytic system (CuCl sole catalyst), wide range could be obtained in moderate to good yields. Notably, use Na15NO2 produce 15N-labeled diarylamines, which would otherwise difficult prepare by known methods.

Language: Английский

Ipso-Nitration of Boronic Esters Enabled by Ferric Nitrate Nonahydrate (Fe(NO3)3·9H2O) in HFIP DOI

Yuzhu Zheng,

Zongyi Liu,

Qing Huang

et al.

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

Published: March 13, 2025

We describe in this work an operationally facile and generally applicable ipso-nitration of boronic esters by Fe(NO3)3·9H2O hexafluoroisopropanol (HFIP), allowing us fast access to various nitroarenes that are currently difficult obtain via traditional electrophilic C–H nitrations. In contrast previous deborylative ipso-nitrations, new protocol utilized less reactive more stable organoboron reagents therefore had significantly improved substrate scope functional group tolerance, which was exemplified the late-stage natural products, pharmaceuticals, biologically active molecules.

Language: Английский

Citations

1
Cu-Catalyzed Synthesis of Symmetric Diarylamines from Organoboronic Acids Using NaNO2 as the Amino Source DOI
Daming Liu,

Hui You,

Shuo Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

A copper-catalyzed novel synthesis of symmetric diarylamines was achieved from aryl boronic acids and NaNO2. This protocol employs as the commercially available arylation reagents sodium nitrite (NaNO2) cheap, stable, solid amino source. Under a simple ligand- base-free copper catalytic system (CuCl sole catalyst), wide range could be obtained in moderate to good yields. Notably, use Na15NO2 produce 15N-labeled diarylamines, which would otherwise difficult prepare by known methods.

Language: Английский

Citations

0