Regio- and Stereoselective Electro-Mediated Carboalkoxylation of 1,3-Dienes DOI

Ophélie Montiège,

Marion Siccardi,

Morgane Sanselme

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(51), P. 11105 - 11110

Published: Dec. 16, 2024

1,3-Dienes are versatile raw materials for building molecular complexity. We report herein mild conditions the regio- and stereoselective [only (E) isomer obtained] 1,4-carboalkoxylation of 1,3-dienes. This electrochemical multicomponent reaction provides an eco-efficient straightforward access to a diverse range (E)-polyfunctionalized allyl ether products, without requiring any metal catalyst.

Language: Английский

Photoinduced Copper‐Catalyzed Asymmetric Three‐Component Radical 1,2‐Azidooxygenation of 1,3‐Dienes DOI
Guo‐Qing Li, Ziqing Li, Min Jiang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(32)

Published: May 24, 2024

Abstract Radical‐involved multicomponent difunctionalization of 1,3‐dienes has recently emerged as a promising strategy for rapid synthesis valuable allylic compounds in one‐pot operation. However, the expansion radical scope and enantiocontrol remain two major challenges. Herein, we describe an unprecedented photoinduced copper‐catalyzed highly enantioselective three‐component 1,2‐azidooxygenation with readily available azidobenziodazolone reagent carboxylic acids. This mild protocol exhibits broad substrate scope, high functional group tolerance, exceptional control over chemo‐, regio‐ enantioselectivity, providing practical access to diverse azidated chiral esters. Mechanistic studies imply that copper complex is implicated bifunctional catalyst both photoredox catalyzed azidyl generation C−O cross‐coupling.

Language: Английский

Citations

12
A concise review on copper catalyzed synthesis of α-ketoamides DOI Creative Commons
Amit Gautam, Biswa Ranjan Swain,

Sonali B. Jethy

et al.

Applied Catalysis O Open, Journal Year: 2025, Volume and Issue: unknown, P. 207039 - 207039

Published: March 1, 2025

Language: Английский

Citations

0
Cu-Catalyzed Asymmetric Three-Component Radical Acylarylation of Vinylarenes with Aldehydes and Aryl Boronic Acids DOI
Zhiheng Li, Shang Wang, Si‐Cong Chen

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(47), P. 32235 - 32242

Published: Nov. 13, 2024

The direct use of readily available aldehydes as acyl radical precursors has facilitated diverse three-component acylative difunctionalization reactions alkenes, offering a powerful route to synthesize β-branched ketones. However, asymmetric alkenes with still remains elusive. Here we report copper-catalyzed acylarylation vinylarenes and aryl boronic acids. This method begins formation from an aldehyde via hydrogen atom transfer. adds the alkene, forming new benzylic that then undergoes enantioselective arylation. A chiral binaphthyl-tethered bisoxazoline ligand is essential for achieving high stereocontrol. strategy enables synthesis range synthetically valuable β,β-diaryl ketones vinylarenes.

Language: Английский

Citations

3
A concise review on copper catalyzed synthesis of α-ketoamides DOI Creative Commons
Sharada Prasanna Swain, Amit Gautam

Published: Jan. 18, 2024

The α-keto-amides are essential building blocks for the synthesis of β-lactams and oxazolidinones. As it contains multiple reactive centers, could be a suitable starting material following reactions such as Michael addition reaction, Pictet–Spengler Mannich, Stetter reaction etc. There many US FDA approved drug molecules which bear α-keto amid moieties, boceprevir, telaprevir, fostemsavir, varespladib Copper-catalyzed α-ketoamides from acetophenones, aryl acetic acids, alkynes, acetaldehydes, α-azido ketones, 1,3-diketo compounds have been reported. This review describes research articles (since year 2012) related copper-catalyzed amides mechanism those reactions.

Language: Английский

Citations

1
Photoinduced Copper‐Catalyzed Asymmetric Three‐Component Radical 1,2‐Azidooxygenation of 1,3‐Dienes DOI
Guo‐Qing Li, Ziqing Li, Min Jiang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(32)

Published: May 24, 2024

Abstract Radical‐involved multicomponent difunctionalization of 1,3‐dienes has recently emerged as a promising strategy for rapid synthesis valuable allylic compounds in one‐pot operation. However, the expansion radical scope and enantiocontrol remain two major challenges. Herein, we describe an unprecedented photoinduced copper‐catalyzed highly enantioselective three‐component 1,2‐azidooxygenation with readily available azidobenziodazolone reagent carboxylic acids. This mild protocol exhibits broad substrate scope, high functional group tolerance, exceptional control over chemo‐, regio‐ enantioselectivity, providing practical access to diverse azidated chiral esters. Mechanistic studies imply that copper complex is implicated bifunctional catalyst both photoredox catalyzed azidyl generation C−O cross‐coupling.

Language: Английский

Citations

0
Regio- and Stereoselective Electro-Mediated Carboalkoxylation of 1,3-Dienes DOI

Ophélie Montiège,

Marion Siccardi,

Morgane Sanselme

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(51), P. 11105 - 11110

Published: Dec. 16, 2024

1,3-Dienes are versatile raw materials for building molecular complexity. We report herein mild conditions the regio- and stereoselective [only (E) isomer obtained] 1,4-carboalkoxylation of 1,3-dienes. This electrochemical multicomponent reaction provides an eco-efficient straightforward access to a diverse range (E)-polyfunctionalized allyl ether products, without requiring any metal catalyst.

Language: Английский

Citations

0