Electrochemical Preparation and Transformation of Sulfonium Salts DOI Creative Commons
Takuya Michiyuki, Lutz Ackermann

ChemElectroChem, Год журнала: 2025, Номер unknown

Опубликована: Март 5, 2025

Abstract Sulfonium salts are typically bench‐stable and readily available reagents that showcase diverse chemical reactivities. Owing to these synthetically valuable features, sulfonium salt chemistry has witnessed considerable momentum over the past decades. Particularly, merger of electrosynthesis enabled utilization electric current in place cost‐intensive hazardous redox agents maximize attractive characteristics salts. Additionally, electrochemistry allowed chemists dial desired potential, offering selective access target products otherwise unattainable by either thermal or photochemical manifolds. These advantages led major advances chemistry. Thus, we, herein, provide an overview early pioneering findings recent progress devoted organic associated with until December 2024, aiming stimulate future this rapidly evolving arena.

Язык: Английский

Thianthrenation-Enabled Pyrrolidin-2-yl and Tetrahydrofuran-2-yl Methylation of (Hetero)Arenes DOI
Boyu Peng, Licheng Dai, Ruzhang Liu

и другие.

Organic Letters, Год журнала: 2023, Номер 25(15), С. 2606 - 2610

Опубликована: Апрель 11, 2023

The mild and efficient palladium-catalyzed pyrrolidin-2-yl tetrahydrofuran-2-yl methylation of (hetero)arenes has been developed. A wide range underwent the regioselective thianthrenation to generate arylthianthrenium triflate, developed Pd-catalyzed alkene carboamination carboalkoxylation reactions afforded corresponding biologically important pyrrolidine tetrahydrofuran derivatives. Mechanistic studies indicated that this reaction proceeds through a syn-heteropalladation mechanistic pathway. demonstrated late-stage functionalization enantioselective will help promote potential application established method in organic synthesis related fields.

Язык: Английский

Процитировано

11

Recent Advances in Electro- or Photochemical Driven Transformations via Cleavage of the C–N Bond of Quaternary Ammonium Salts DOI
X. KONG, Zhong‐Yan Cao, Xiaohui Chen

и другие.

Synthesis, Год журнала: 2023, Номер 55(18), С. 2833 - 2842

Опубликована: Янв. 26, 2023

Abstract Selective functionalization via cleavage of the C–N bond amines has proven to be challenging partly because its relatively high dissociation energy, even though are abundant and readily available. To meet this challenge, many new transformations based on pre-activation before have been developed. Among them, conversion into quaternary ammonium salts certain advantages, such as easy preparation from primary, secondary, or tertiary amines, well stable storage usage. Although transition metal catalysis frequently applied for developing oxidative addition salts, recent studies shown a dimension by using green electro- photochemical tools. In short review, advances in electro-, photo-, photoelectrochemical driven synthetic applications summarized discussed. 1 Introduction 2 Electrochemical Driven Transformations 3 Photochemical 4 Photoelectrochemical 5 Conclusion Outlook

Язык: Английский

Процитировано

10

Recent progress in sulfonyl fluoride synthesis via the radical sulfur dioxide insertion and fluorination strategy DOI

Haozhen Zhang,

Wangchuan Xiao,

Fanhong Wu

и другие.

Science China Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 8, 2024

Язык: Английский

Процитировано

4

Aryl sulfonyl fluoride synthesisviapalladium-catalyzed fluorosulfonylation of aryl thianthrenium salts DOI
Lingling Shan,

Zhanhu Ma,

Caiyun Ou

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(18), С. 3789 - 3793

Опубликована: Янв. 1, 2023

We developed an efficient palladium-catalyzed fluorosulfonylation reaction of aryl thianthrenium salts to smoothly prepare various sulfonyl fluorides using cheap Na2S2O4 as a convenient source in combination with N-fluorobenzenesulfonimide (NFSI) ideal fluorine under mild reduction conditions. A one-pot synthesis starting from arenes was established well without the need for separating salts. The practicality this protocol demonstrated by gram-scale synthesis, derivatization reactions, and excellent yields.

Язык: Английский

Процитировано

9

Electrochemical Preparation and Transformation of Sulfonium Salts DOI Creative Commons
Takuya Michiyuki, Lutz Ackermann

ChemElectroChem, Год журнала: 2025, Номер unknown

Опубликована: Март 5, 2025

Abstract Sulfonium salts are typically bench‐stable and readily available reagents that showcase diverse chemical reactivities. Owing to these synthetically valuable features, sulfonium salt chemistry has witnessed considerable momentum over the past decades. Particularly, merger of electrosynthesis enabled utilization electric current in place cost‐intensive hazardous redox agents maximize attractive characteristics salts. Additionally, electrochemistry allowed chemists dial desired potential, offering selective access target products otherwise unattainable by either thermal or photochemical manifolds. These advantages led major advances chemistry. Thus, we, herein, provide an overview early pioneering findings recent progress devoted organic associated with until December 2024, aiming stimulate future this rapidly evolving arena.

Язык: Английский

Процитировано

0