Visible-Light-Mediated Borylation of Arenes via an Electron Donor–Acceptor Complex of Thianthrenium Salts

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 4, 2025

Aryl borates are one of the most important synthetic materials in organic synthesis. Herein, we report a visible-light-induced electron donor-acceptor (EDA)-based borylation protocol between thianthrenium salts and 1,4-diazabicyclo[2.2.2]octane (DABCO) for synthesis various aryl boronates without photocatalyst or stepwise processing. Remarkably, this photochemical strategy is compatible with wide range sensitive functional groups affords excellent yields. Moreover, quantitative recovery thianthrene feedstock lowers reaction cost.

Language: Английский

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

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 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

Language: Английский

CCl₄-Induced Synthesis of Phosphonothioates, Sulfoxides, and Sulfones from Sodium Sulfinates

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 22, 2025

An external reductant-free and acid-free synthesis of phosphonothioates from odorless sodium sulfinates induced by CCl4 (1.0 equiv) under mild conditions has been achieved. This transformation provides an efficient synthetic approach to in up 98% yield with good functional group compatibility. In addition, unexpected CCl4-induced sulfoxides sulfones using DMSO as the solvent developed.

Language: Английский