Regiodivergent C−H Acylation of Arenes by Switching from Ionic‐ to Radical‐Type Chemistry Using NHC Catalysis DOI

Jannik Reimler,

Xiaoye Yu,

Nico Spreckelmeyer

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(27)

Published: April 24, 2023

The Friedel-Crafts acylation reaction, which belongs to the class of electrophilic aromatic substitutions is a highly valuable and versatile reaction in synthesis. Regioselectivity predictable determined by electronic as well steric factors (hetero)arene substrate. Herein, radical approach for arenes heteroarenes presented. C-H achieved through mild cooperative photoredox/NHC catalysis with cross-coupling an arene cation NHC-bound ketyl key step. As compared classical acylation, regiodivergent outcome observed upon switching from ionic mode. In these divergent reactions, aroyl fluorides act reagents both process.

Language: Английский

Electro‐Synthesis of Organic Compounds with Heterogeneous Catalysis DOI Creative Commons
Tariq Ali, Haiyan Wang, Waseem Iqbal

et al.

Advanced Science, Journal Year: 2022, Volume and Issue: 10(1)

Published: Nov. 18, 2022

Electro-organic synthesis has attracted a lot of attention in pharmaceutical science, medicinal chemistry, and future industrial applications energy storage conversion. To date, there not been detailed review on electro-organic with the strategy heterogeneous catalysis. In this review, most recent advances synthesizing value-added chemicals by catalysis are summarized. An overview electrocatalytic oxidation reduction processes as well paired electrocatalysis is provided, anodic alcohols (monohydric polyhydric), aldehydes, amines discussed. This also provides in-depth insight into cathodic carboxylates, carbon dioxide, CC, C≡C, reductive coupling reactions. Moreover, electro-synthesis methods, including parallel paired, sequential divergent convergent electrolysis, Additionally, strategies developed to achieve high electrosynthesis efficiency associated challenges addressed. It believed that promising direction organic electrochemistry, offering numerous opportunities develop new reaction methods.

Language: Английский

Citations

61
Recent progress on electrochemical synthesis involving carboxylic acids DOI

Na Chen,

Zenghui Ye, Fengzhi Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(25), P. 5501 - 5520

Published: Jan. 1, 2021

Recent progress on sustainable electrochemical synthesis involving carboxylic acids was reviewed.

Language: Английский

Citations

57
Nickel catalyzed multicomponent stereodivergent synthesis of olefins enabled by electrochemistry, photocatalysis and photo-electrochemistry DOI Creative Commons
Chen Zhu, Huifeng Yue, Magnus Rueping

et al.

Nature Communications, Journal Year: 2022, Volume and Issue: 13(1)

Published: June 10, 2022

Trisubstituted alkenes are important organic synthons and have broad applications in the synthesis of many pharmaceuticals materials. The stereoselective such compounds has long been a research focus for researchers. Herein, we report three-component, reductive cascade, cross-coupling reaction arylalkylation alkynes. A wide range trisubstituted obtained good to high yields with excellent chemo- stereoselectivity by switching between electrochemistry photocatalysis. E isomer product is exclusively when conducted electricity nickel, while Z generated photo- nickel dual catalysts used. Moreover, photo-assisted electrochemically enabled catalyzed protocol demonstrated selectively deliver Z-trisubstituted without addition photocatalysts.

Language: Английский

Citations

53
Advances in Organic Electrochemical Synthesis DOI Open Access
Zhen‐Hua Wang, Cong Ma, Ping Fang

et al.

Acta Chimica Sinica, Journal Year: 2022, Volume and Issue: 80(8), P. 1115 - 1115

Published: Jan. 1, 2022

Organic electrochemical synthesis has become a useful and environmentally friendly alternative to traditional organic been applied oxidation, reduction, or redox neutral transformation.By dialing in the electric current electrode potential, it is possible achieve some challenging transformations under mild reaction conditions.With increasing awareness of energy efficiency environmental protection, attracted much attention recent years.However, faces several challenges including passivation, limited types, difficulty controlling reactivity selectivity, so on.This review focuses on solution system, summarizes efforts addressing these through direct electrolysis indirect electrolysis.In electrolysis, strategies include rational design reactions, change modes equipment, merging technology with other novel synthetic technologies.In terms compounds transition metals are mainly used as molecular electrocatalysts shuttle electrons between electrodes substrates control affording chemical transformations.

Language: Английский

Citations

39
Regiodivergent C−H Acylation of Arenes by Switching from Ionic‐ to Radical‐Type Chemistry Using NHC Catalysis DOI

Jannik Reimler,

Xiaoye Yu,

Nico Spreckelmeyer

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(27)

Published: April 24, 2023

The Friedel-Crafts acylation reaction, which belongs to the class of electrophilic aromatic substitutions is a highly valuable and versatile reaction in synthesis. Regioselectivity predictable determined by electronic as well steric factors (hetero)arene substrate. Herein, radical approach for arenes heteroarenes presented. C-H achieved through mild cooperative photoredox/NHC catalysis with cross-coupling an arene cation NHC-bound ketyl key step. As compared classical acylation, regiodivergent outcome observed upon switching from ionic mode. In these divergent reactions, aroyl fluorides act reagents both process.

Language: Английский

Citations

34