Modular synthesis of conjugated enamidines and cascade annulation toward benzofuran-3-oxoacetate DOI
Yao Liu, Ruiqi Wang, Qinheng Zheng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2047 - 2053

Published: Jan. 1, 2024

A three-component reaction of aryne, DMF and isonitrile for the synthesis otherwise inaccessible chemotype, conjugated enamidines, is developed. Incubation with a Brønsted acid causes cascade skeleton rearrangement enamidines to benzofuran-3-oxoacetates.

Language: Английский

Construction of α-Acyloxy Ketones via Photoredox-Catalyzed O–H Insertion of Sulfoxonium Ylides with Carboxylic Acids DOI
Qing Sun, Altman Yuzhu Peng, Yujing Wang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(36), P. 6613 - 6617

Published: Sept. 6, 2023

Herein, a photoredox-catalyzed insertion of sulfoxonium ylides with carboxylic acids was advanced under mild and simple conditions, offering practical approach for preparing α-acyloxy ketones broad scope acids. A combined experimental computational study suggests that this reaction proceeds via stepwise proton-assisted electron transfer mechanism.

Language: Английский

Citations

18
Photochemical Functionalization of 4-Diazoisoquinoline-1,3(2H,4H)-diones and Their 1-Sulfoxide Analogues DOI Creative Commons
Joseph P. Milton, Dorota Gryko

ACS Organic & Inorganic Au, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

Language: Английский

Citations

0
Theoretical Analysis of a Three-Component Reaction between Two Diazo Compounds and a Hydroxylamine Derivative: Mechanism, Enantioselectivity, and Effect of Cooperative Catalysis DOI

Simeng Qi,

Ji Ma,

Guowei Yan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(24), P. 17215 - 17226

Published: Nov. 30, 2023

The mechanism, enantioselectivity, and effect of chiral phosphoric acid (CPA) cocatalyst were investigated by the density functional theory (DFT) for three-component asymmetric aminohydroxylation between two diazo compounds a hydroxylamine derivative. This type cascade process is cooperatively catalyzed Rh2(OAc)4 CPA. obtained results clearly indicate that first step global reaction involves nucleophilic attack at nitrogen center N-hydroxyaniline rhodium-carbene intermediates producing imines. Subsequently, an enolate intermediate was recognized as key species generated from second compound leaving benzyl alcohol (BnOH) fragment in presence same dirhodium catalyst. Then, terminated Mannich-type addition, delivering products S-R conformation with assistance acid. distortion/interaction analysis shows relative distortions CPA enol play vital role energy ordering stereocontrolling transition states (TSs). Furthermore, influence different substituents fully rationalized analysis. study opens up novel synthetic possibilities improves predictability when exploring related types organic transformations.

Language: Английский

Citations

5
Modular synthesis of conjugated enamidines and cascade annulation toward benzofuran-3-oxoacetate DOI
Yao Liu, Ruiqi Wang, Qinheng Zheng

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 2047 - 2053

Published: Jan. 1, 2024

A three-component reaction of aryne, DMF and isonitrile for the synthesis otherwise inaccessible chemotype, conjugated enamidines, is developed. Incubation with a Brønsted acid causes cascade skeleton rearrangement enamidines to benzofuran-3-oxoacetates.

Language: Английский

Citations

1