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

Roshan I. Patel,

Barakha Saxena,

Anuj Sharma

и другие.

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

A Catalyst- and Thiol-Free Protocol for Arene C–H Thioetherification via Photoactive Electron Donor–Acceptor Complexes DOI
Ang Gao,

Hongqiong Liu,

Yanan Zhou

и другие.

Green Chemistry, Год журнала: 2025, Номер 27(8), С. 2286 - 2292

Опубликована: Янв. 1, 2025

We present a catalyst- and thiol-free protocol for arene C–H thioetherification under visible light irradiation.

Язык: Английский

Процитировано

0
Visible-Light-Induced NHC-Catalyzed Carboacylation Reaction of Alkenes from Aryl Thianthrenium Salts and Aldehydes DOI

Dong-Sheng Ji,

Youwan Ye,

Peiqin Zhang

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 21, 2025

A metal-free, visible-light-induced NHC-catalyzed multiple-component reaction involving aldehydes and aryl thianthrenium salts for the carboacylation of alkenes is reported. In this reaction, NHC-activated afforded Breslow intermediates, which reduced generated radicals. The resulting radicals underwent radical addition reactions to yield arylacylation products, in presence iodoalkane, participated halogen atom transfer process generate alkyl facilitate olefin alkylacylation.

Язык: Английский

Процитировано

0
Photocatalytically switchable chemoselective difluoramidation of olefins for the synthesis of diversified difluoro-γ-lactams DOI

Tian-Zheng Cao,

Cai-Jian Nie,

Jing Li

и другие.

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

This study demonstrates a visible-light-driven intramolecular alkene difluorination enabling Heck-type coupling, hydrofluoramidation, and difunctionalization. Diverse difluoro-γ-lactams were synthesized with high selectivity substrate generality.

Язык: Английский

Процитировано

0
Visible Light‐Induced Arylation/Alkylation/Phosphorylation of Isocyanides viaEDA Complex Activation DOI Open Access

Shichao Yang,

Xiangwen Tan,

Dan Liu

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 20, 2025

Comprehensive Summary Herein, it is reported that the aryl radicals derived from thianthrenium salts are used as coupling partner in arylation reactions of isocyanides, simultaneously initiators for formation alkyl and phosphoryl ethers diarylphosphine oxides. This cascade cyclization reaction leads to diverse arylated, alkylated phosphorylated heteroaromatic compounds. Notably, this transformation can be achieved without aid metals or photocatalysts, exhibiting a wide substrate applicability operational simplicity. Mechanistic studies suggest involvement radical processes electron donor‐acceptor (EDA) complexes transformation.

Язык: Английский

Процитировано

0
Site-Selective Copper–N-Heterocyclic Carbene-Catalyzed C(sp2)–C(sp) Cross-Coupling of Aryl Thianthrenium Salts DOI
Jin Zhang, Hangsheng Yang, Li Sun

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 23, 2025

This work demonstrates Cu–NHC (NHC = N-heterocyclic carbene) catalyzed alkynylation of aryl thianthrenium salts via thiazol-2-ylidene ligands, achieving a Pd-free Sonogashira coupling with broad substrate compatibility and functional group tolerance. Late-stage pharmaceutical rare alkynylative C–H functionalization/ring-opening pathways are enabled. Thiazol-2-ylidenes, featuring "half-umbrella"-shaped geometry, exhibit superior catalytic performance over traditional imidazol-2-ylidenes, underscoring their unique ligand efficacy. catalysis enables the use as versatile electrophiles for diverse cross-couplings under mild conditions.

Язык: Английский

Процитировано

0
Visible-Light-Mediated Borylation of Arenes via an Electron Donor–Acceptor Complex of Thianthrenium Salts DOI
Tao Liu, Cai Yiping, Qin‐Hua Song

и другие.

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

Опубликована: Май 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.

Язык: Английский

Процитировано

0
Photoactivation of Thianthrenium Salts: An Electron-Donor–Acceptor (EDA)-Complex Approach DOI

Roshan I. Patel,

Barakha Saxena,

Anuj Sharma

и другие.

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

Процитировано

0