Electrochemical Oxidative Dearomatization of Electron-deficient Phenols Using Br⁺/Br^– Catalysis

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

An electrochemical method for oxidative dearomatization of electron-deficient phenols is reported, using tetrabutylammonium bromide as a catalytic mediator under aqueous biphasic conditions.

Язык: Английский

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General Electron-Donor-Acceptor Complex Mediated Thioesterification Reaction via Site-Selective C-H Functionalization using Aryl Sulfonium Salts

Green Chemistry, Год журнала: 2024, Номер 26(19), С. 10265 - 10274

Опубликована: Янв. 1, 2024

We herein describe a versatile electron–donor–acceptor (EDA) mediated thioesterification reaction using aryl sulfonium salt (acceptor) with potassium thioacid salts (donor) under visible light irradiation.

Язык: Английский

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Photo-driven Aerobic C(sp3)-H Oxidation by Organic Photocatalysts: A Recent Review

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134496 - 134496

Опубликована: Янв. 1, 2025

Язык: Английский

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Green and sustainable site- and cross-selective C-H reductive coupling of para-quinone methides with quinoxaline-2(1H)-ones

Green Synthesis and Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Апрель 1, 2025

Язык: Английский

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1,2-Acyl transposition through photochemical skeletal rearrangement of 2,3-dihydrobenzofurans

Science, Год журнала: 2025, Номер 388(6747), С. 631 - 638

Опубликована: Май 8, 2025

Saturated heterocycles are commonly adorned with groups that influence their biological properties. Synthetic methods transpose existing substituents on saturated to multiple peripheral positions therefore highly valuable. In this work, we report a formal 1,2-acyl transposition through the photochemical exchange of C 2 –C 3 -acylated dihydrobenzofurans. This strategy relies an unusual isomerization dihydrobenzofuran core electrophilic spiro-cyclopropane intermediate is then intercepted by halide nucleophile. A variety aryl ketones transposed using 370-nanometer centered irradiation. Additionally, carboxylic acids, esters, and amides can be 310-nanometer work highlights power skeletal rearrangement achieve net modification.

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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Cumene-to-Phenol Process Mediated by Bromine Radicals through Photoinduced Ligand-to-Metal Charge Transfer

Synlett, Год журнала: 2025, Номер unknown

Опубликована: Май 16, 2025

Abstract Selective C–H activation via hydrogen atom transfer (HAT) has gained significant interest recently. One industrial application for HAT can be found in the tertiary benzylic bond of cumene producing phenol, a versatile chemical feedstock various industries. However, overall phenol yield remains low using existing Hock process due to poor selectivity towards key reaction intermediate, hydroperoxide (CHP). Here, we demonstrate an efficient strategy production through photooxidation CHP iron bromide under blue light irradiation, where bromine radicals (generated situ ligand-to-metal charge transfer) are used as abstractors. Mechanistic studies revealed cumene-to-CHP conversion occurred abstraction by radical mechanism, and acetic acid water additives increased stabilizing peroxides. The cumene-phenol achieved up 88% 1 hour could with wide range substrates. We thus developed selective, mild, method photooxidative conditions.

Язык: Английский

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Site-Selective Access to Functionalized Pyrroloquinoxalinones via H-Atom Transfer from N═C_sp²–H Bonds of Quinoxalinones

Organic Letters, Год журнала: 2024, Номер 26(43), С. 9244 - 9250

Опубликована: Окт. 23, 2024

Site-selective hydrogen atom transfer (HAT) from the N═C

Язык: Английский

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