Recent Advances in the Application of Selectfluor as a Versatile Reactant in Organic Photo‐ and Electrochemical Synthesis

ChemistrySelect, Год журнала: 2025, Номер 10(7)

Опубликована: Фев. 1, 2025

Abstract Selectfluor [1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo‐[2.2.2]octane bis(tetrafluoroborate)] is a versatile reagent in organic synthetic chemistry. As renowned electrophilic fluorinating agent, widely acknowledged as crucial source of fluorine for various fluorination reactions. Moreover, it employed “fluorine‐free” comprising transition metal oxidant, anion, and radical initiator; achieving other transformations. Notably, can also serve an amine or methylene synthesis. Recently, there has been growing interest the application reactant photo‐ electrochemistry. In this review, comprehensive overview Selectfluor's electrochemical strategies over past decade, provided.

Язык: Английский

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Photoactivation of Thianthrenium Salts: An Electron-Donor–Acceptor (EDA)-Complex Approach

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 14, 2025

Thianthrenium salts have emerged as one of the most versatile reagents, gaining significant popularity within synthetic community for their utility in construction C-C and C-X (X = N, O, S, P, halogens) bonds. The use photoredox transition metal catalysis with thianthrenium C-heteroatom bond formation is well established. However, these methods require elevated temperatures, expensive catalysts, ligands under stringent conditions effective execution. In contrast, photocatalysis- transition-metal-free approaches constructing bonds using salt derivatives become increasingly sought after. this regard, electron-donor-acceptor (EDA)-complex reactions a powerful strategy organic synthesis, eliminating need photocatalysts visible light irradiation. EDA-complex photochemistry exploits electron-acceptor properties salts, facilitating rapid generation radical intermediates via C-S cleavage. These play pivotal role enabling variety valuable formations. Perspective, we highlight advances EDA-complex-mediated involving mechanisms, substrate scope, limitations For sake brevity, article organized into five main sections: (1) Nitrogen-based donor reactions, (2) Oxygen-based (3) Sulfur-based (4) Phosphorus-based (5) π-based focus on C-C, C-S, C-B C-P

Язык: Английский

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Photoelectrocatalytic [4+2] Annulation for S‐Heterocycle Assembly Enabled by Proton‐Coupled Electron Transfer (PCET)

Chemistry - A European Journal, Год журнала: 2024, Номер 30(59)

Опубликована: Авг. 3, 2024

Abstract Cross‐dehydrogenative couplings (CDC) present an efficient strategy for the assembly of biorelevant heterocycles, but are thus far largely limited to toxic transition metals and rather harsh reaction conditions. In sharp contrast, we, herein report on a mild photoelectrocatalyzed CDC‐[4+2] annulation enabling synthesis functionalized isothiochromenes enabled by proton‐coupled electron transfer (PCET) strategy. The transformative photoelectrocatalysis obviated transition‐metal, high temperatures, stoichiometric chemical redox reagents. This approach was characterized exceedingly conditions, ample substrate scope, commercially available catalyst. Gram‐scale reactions telescoped route reflected unique potential in green important S ‐heterocycles.

Язык: Английский

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Visible Light-Induced Ruthenium(II)-Catalyzed Hydroarylation of Unactivated Olefins

Chemical Science, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Ruthenium-catalyzed photo-induced hydroarylation at room temperature shows high functional group tolerance allowing to incorporate biorelevant motifs. Mechanistic studies provided in-depth details on the light's role generate active catalyst.

Язык: Английский

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