Molecular Oxygen‐Induced Transamidation of Unactivated Amides in Diethyl Carbonate in the Presence of a Palladium Catalyst DOI Creative Commons
Garazi Urgoitia,

Maria Obieta,

María Teresa Herrero

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4713 - 4725

Published: Nov. 9, 2023

Abstract Herein we disclose a palladium‐catalyzed procedure for the transamidation of structurally diverse amides with amines based on use molecular oxygen as palladium‐activating agent. The reaction, which is scalable and amenable preparation enantioenriched compounds, carried out in bio‐degradable solvent often used fuel additive, diethyl carbonate. As result 10 −4 mol% catalyst required, final products are isolated containing palladium impurities concentration 0.1 ppm. Two kinetically different mechanistic pathways proposed this reaction account number experiments such kinetic curves, TEM images, poisoning experiments, UPLC‐ESI‐MS identification intermediates EPR spectra crude.

Language: Английский

Amidation of β‐Keto Sulfonyl Fluorides via C–C Bond Cleavage DOI

Hui Liang,

Qian Liu,

Xueyan Zhao

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(27)

Published: May 22, 2024

Abstract A simple protocol for amide bond construction using β‐keto sulfonyl fluorides (BKSFs) as the acyl surrogates has been achieved. The reaction of BKSFs with a range amines could be performed in presence N ‐bromosuccinimide (NBS), affording various amides diverse functionalities. Preliminary mechanistic studies revealed that dibromo‐substituted key intermediate this amidation process.

Language: Английский

Citations

2
Molecular Oxygen‐Induced Transamidation of Unactivated Amides in Diethyl Carbonate in the Presence of a Palladium Catalyst DOI Creative Commons
Garazi Urgoitia,

Maria Obieta,

María Teresa Herrero

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4713 - 4725

Published: Nov. 9, 2023

Abstract Herein we disclose a palladium‐catalyzed procedure for the transamidation of structurally diverse amides with amines based on use molecular oxygen as palladium‐activating agent. The reaction, which is scalable and amenable preparation enantioenriched compounds, carried out in bio‐degradable solvent often used fuel additive, diethyl carbonate. As result 10 −4 mol% catalyst required, final products are isolated containing palladium impurities concentration 0.1 ppm. Two kinetically different mechanistic pathways proposed this reaction account number experiments such kinetic curves, TEM images, poisoning experiments, UPLC‐ESI‐MS identification intermediates EPR spectra crude.

Language: Английский

Citations

4