Electrochemical Ferrier Rearrangement of Glycals DOI

Chun Qi,

Giulio Goti, Andrea Sartorel

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9328 - 9333

Published: Oct. 21, 2024

The Ferrier rearrangement (FR) is a well-documented reaction that relies on strong acids or oxidants to convert glycals into unsaturated glycosyl derivatives. In this work, we introduce an electrochemical variant of the FR, offering broad substrate compatibility. Various nucleophiles and glycal derivatives afford 2,3-unsaturated in high yields with excellent diastereoselectivities. This sustainable method promises expand electrochemistry applications sugar chemistry.

Language: Английский

Enhancing electrochemical reactions in organic synthesis: the impact of flow chemistry DOI Creative Commons
Morgan Regnier, Clara Vega, Dimitris I. Ioannou

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Utilizing electrons directly offers significant potential for advancing organic synthesis by facilitating novel reactivity and enhancing selectivity under mild conditions. As a result, an increasing number of chemists are exploring electrosynthesis. However, the efficacy electrochemical transformations depends critically on design cell. Batch cells often suffer from limitations such as large inter-electrode distances poor mass transfer, making flow promising alternative. Implementing cells, however, requires foundational understanding microreactor technology. In this review, we briefly outline applications electrosynthesis before providing comprehensive examination existing reactor technologies. Our goal is to equip with insights needed tailor their meet specific requirements effectively. We also highlight application designs in scaling up processes integrating high-throughput experimentation automation. These advancements not only enhance synthetic community but hold promise both academia industry.

Language: Английский

Citations

9
Asymmetric cyclopropanation via electro-organocatalytic cascade DOI Creative Commons
Anastasiya Krech, Marharyta V. Laktsevich‐Iskryk,

Nora Deil

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The work demonstrates the successful merger of electrochemistry with asymmetric iminium ion organocatalysis.

Language: Английский

Citations

3
Electrochemically Driven Metal-Free Synthesis of Benzylic Thioethers via C-S Cross-Coupling DOI

Ming-Qiu-Hao Fu,

Yan‐Hong He, Zhi Guan

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6790 - 6796

Published: Jan. 1, 2024

An electrochemically driven C–S radical–radical cross-coupling reaction between benzyl halides and disulfides for the synthesis of benzylic thioethers has been developed under environmentally friendly mild conditions.

Language: Английский

Citations

1
Electrochemical Ferrier Rearrangement of Glycals DOI

Chun Qi,

Giulio Goti, Andrea Sartorel

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9328 - 9333

Published: Oct. 21, 2024

The Ferrier rearrangement (FR) is a well-documented reaction that relies on strong acids or oxidants to convert glycals into unsaturated glycosyl derivatives. In this work, we introduce an electrochemical variant of the FR, offering broad substrate compatibility. Various nucleophiles and glycal derivatives afford 2,3-unsaturated in high yields with excellent diastereoselectivities. This sustainable method promises expand electrochemistry applications sugar chemistry.

Language: Английский

Citations

0