Electro-Oxidative Platform for Nucleophilic α-Functionalization of Ketones DOI Creative Commons
Rakesh Mondal,

Nicolas Jacob,

Maxime Devuyst

et al.

Published: Nov. 1, 2023

The significance of α-functionalization carbonyl compounds arises from its frequent use in synthetic organic chemistry. Consequently, there is a substantial and constant demand for the creation strategies that facilitate efficient execution such valuable transformation. In this context, herein presented universal electrochemical oxidative platform α- derivatization ketones with nucleophiles, employing an umpolung reactivity. This approach has been successfully employed five distinct transformations involving C-C C-X bond formation via straightforward nucleophilic substitution or cycloaddition reaction pathways. Furthermore, implementation methodology flow using commercially available reactor demonstrated inherent scalability.

Language: Английский

Synthesis of Diverse 4‐Pyrrolin‐2‐ones by Electrochemically Induced Dehydrogenative Regioselective Cyclization of 3‐Aza‐1,5‐dienes and 1,3‐Dicarbonyl Compounds DOI
Xing Ji,

Run He,

Lou Shi

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(11)

Published: Jan. 20, 2024

Abstract A practical and mild electrochemical dehydrogenative regioselective cyclization method has been established for the synthesis of 4‐pyrrolin‐2‐ones using 3‐aza‐1,5‐dienes 1,3‐dicarbonyl compounds as substrates. This protocol is catalyst‐free, metal‐free, does not require oxidizing agents. It exhibits wide substrate compatibility can be easily scaled up to gram scale.

Language: Английский

Citations

9
α-Thiocyanation of Enol Acetates and Sodium Thiocyanate under Electrochemical Conditions DOI
Jinpeng Zhang, Yuliang Qian, Man Ning

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(1), P. 189 - 189

Published: Jan. 1, 2025

Language: Английский

Citations

0
Electro-Oxidative Platform for Nucleophilic α-Functionalization of Ketones DOI
Rakesh Mondal,

Nicolas Jacob,

Julien C. Vantourout

et al.

Synthesis, Journal Year: 2025, Volume and Issue: unknown

Published: April 9, 2025

Abstract The significance of α-functionalization carbonyl compounds arises from its frequent use in synthetic organic chemistry. Consequently, there is a substantial and constant demand for the creation strategies that facilitate efficient execution such valuable transformation. In this context, herein presented universal electrochemical oxidative platform α-derivatization ketones with nucleophiles, employing an umpolung reactivity. This approach has been successfully employed three distinct transformations involving C–C C–X bond formation via straightforward nucleophilic substitution or cycloaddition reaction pathways. Furthermore, implementation methodology flow using commercially available reactor demonstrated inherent scalability.

Language: Английский

Citations

0
Electrochemical Oxidative Reassembly of 1,3-Diketones with Aryl Alkenes and Water via Carbon–Carbon Bond Cleavage Rearrangement DOI
Wei Wu,

R.K. Linghu,

Bingjie Jian

et al.

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

Published: April 25, 2025

We report the electrochemical cleavage and reassembly of 1,3-diketones with aryl alkenes water for synthesis 1,4-ketoalcohol derivatives. This approach represents first example formal carbon-carbon alkene insertion via electro-oxidation, enabling direct diverse derivatives in good to high yields. The developed strategy employs an using inexpensive commercial carbon electrodes undivided cell under mild operationally simple conditions.

Language: Английский

Citations

0
Ferrocene-Mediated Electrochemical Polycyclization of Malonates DOI

Antoine Lefevre,

Régis Guillot,

C. Kouklovsky

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7403 - 7407

Published: Aug. 27, 2024

We report access to the core of biologically relevant aromatic abietane diterpenoids and formal synthesis podocarpic lambertic acids or γ-lactones via an electrochemical bicyclization process initiated by ferrocene-mediated anodic oxidation a malonate single electron-transfer. This approach permits escaping use excess oxidants such as Mn(OAc)3 associated complicated purification.

Language: Английский

Citations

2
Electrochemical Selenized Reaction of N-Arylbicyclo[1.1.0]butane-1-carboxamides: Access to 3-(Arylselanyl)spiro[cyclobutane-1,3′-indolin]-2′-one Derivatives DOI

Jiyao Liu,

Yuliang Qian,

Hongrong Zhao

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15914 - 15923

Published: Oct. 23, 2024

A novel selenized reaction of N-arylbicyclo [1.1.0]butane-1-carboxamides with diselenide for the synthesis polycyclic indoline derivatives is developed under electrochemical conditions. The achieved by bicyclo[1.1.0]butane strain-release and intramolecular cyclization process. In addition, this approach features a wide range substrates, good group tolerance, shorter time, mild

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
Electro-Oxidative Platform for Nucleophilic α-Functionalization of Ketones DOI Creative Commons
Rakesh Mondal,

Nicolas Jacob,

Maxime Devuyst

et al.

Published: Nov. 1, 2023

The significance of α-functionalization carbonyl compounds arises from its frequent use in synthetic organic chemistry. Consequently, there is a substantial and constant demand for the creation strategies that facilitate efficient execution such valuable transformation. In this context, herein presented universal electrochemical oxidative platform α- derivatization ketones with nucleophiles, employing an umpolung reactivity. This approach has been successfully employed five distinct transformations involving C-C C-X bond formation via straightforward nucleophilic substitution or cycloaddition reaction pathways. Furthermore, implementation methodology flow using commercially available reactor demonstrated inherent scalability.

Language: Английский

Citations

0