Visible Light instead of Transition Metal: Electron Donor Acceptor Complex Enabled Cross‐Coupling of Aryl Halides with Active Methylene Compounds DOI Open Access
Alexey A. Volkov, Dmitry I. Bugaenko, Alexander V. Karchava

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 366(3), С. 457 - 464

Опубликована: Дек. 9, 2023

An arylation of anions active methylene compounds with aryl halides provides an access to synthetically versatile α-arylated 1,3-diketones, β-keto esters, nitriles, β-cyano etc. Previously, these C−C cross-coupling reactions have been accomplished only using transition metal-based catalysts. Herein, we demonstrate that arylations can be successfully realized under catalyst-free conditions employing the electron donor-acceptor (EDA) complex photoactivation strategy. The protocol was further optimized for a semi-one pot synthesis indole derivatives via intramolecular coupling.

Язык: Английский

Photo-induced 1,2-alkylarylation/cyclization of alkenes, alkyl halides and N-alkylindoles via an EDA-complex DOI
Tao Ju, Min Ge,

Li-Hang Ren

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(5), С. 1412 - 1419

Опубликована: Янв. 1, 2024

Herein, we developed a photo-induced 1,2-alkylarylation and cyclization of alkenes, alkyl halides N -alkylindoles to synthesize indoles derivatives polysubstituted tetrahydrofuran under mild conditions without the use external redox reagents photosensitizers.

Язык: Английский

Процитировано

3

A general photocatalytic hydrodefluorination and defluoroalkylation of electronically-variable ArCF3 by changing commercially-available arenethiolates DOI

Yuanyang Jiang,

Chenxiu Han,

Zipeng Guo

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(8), С. 4518 - 4527

Опубликована: Янв. 1, 2024

The selection of electronically-different thiolate-based photosensitizers is employed to achieve a precise and specific C–F bond defluorination broad range trifluoromethylarenes, enabling the synthesis 88 α,α-difluoromethyl compounds.

Язык: Английский

Процитировано

3

Photoinduced Phosphoniumation of Aryl Halides and Arylthianthrenium Salts via an Electron Donor–Acceptor Complex DOI
Ziyu Gan, Jia‐Jin Jason Chen, Han Wang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(36), С. 7751 - 7756

Опубликована: Сен. 5, 2024

Owing to their remarkable practicality and utility, phosphonium salts have attracted substantial interest are widely applied in critical areas, such as medicine, materials science, catalysis. Herein, we developed a facile photocatalyst/metal-free synthetic strategy for the preparation of utilizing aryl halides/arylthianthrenium radical precursors. This approach is disclosed undergo an efficient light-induced electron donor-acceptor pathway, facilitating synthesis structurally diverse range salts.

Язык: Английский

Процитировано

3

Visible-light-induced synthesis of bibenzofuranones via a cerium-mediated energy transfer process DOI

J. F. Lv,

Yatao Lang,

Chao‐Jun Li

и другие.

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

Synthesis of bibenzofuranones from benzils via a radical cyclization-dimerization tandem process, efficiently constructing C–O/C–C bonds and contiguous quaternary carbon centers in single step, was reported.

Язык: Английский

Процитировано

0

Visible Light-Induced Highly Regioselective and Stereoselective Oxysulfonylation of Alkynes for the Synthesis of (E)-β-Phenoxy Vinylsulfones DOI
Wenjiao Xie,

Pengju Ma,

Yujun Zhang

и другие.

Organic Letters, Год журнала: 2022, Номер 24(32), С. 6099 - 6104

Опубликована: Авг. 8, 2022

A highly efficient visible light-induced regioselective and stereoselective oxysulfonylation of alkynes with arylsulfonate phenol esters has been developed. This photocatalyst- metal-free method proceeds smoothly under very mild conditions exhibits a broad substrate scope, providing (E)-β-phenoxy vinylsulfones in moderate to excellent yields. Mechanistic studies indicated the involvement an electron donor–acceptor complex-mediated radical process.

Язык: Английский

Процитировано

12

Copper-Catalyzed Thiolation of Hydrazones with Sodium Sulfinates: A Straightforward Synthesis of Benzylic Thioethers DOI
Anand Kumar Pandey,

Shiv Chand,

Anup Sharma

и другие.

The Journal of Organic Chemistry, Год журнала: 2022, Номер 88(1), С. 475 - 482

Опубликована: Дек. 15, 2022

A facile and sustainable protocol for the thiolation of hydrazones with sodium sulfinates has been developed in presence CuBr2 DBU DMF to afford diverse benzylic thioethers. Control experiments reveal a radical pathway involving thiyl as key intermediate.

Язык: Английский

Процитировано

12

Photoinduced Trifluoromethylselenolation of Aryl Halides with [Me4N][SeCF3] DOI
Fei Li, Xue Han, Ziang Xu

и другие.

Organic Letters, Год журнала: 2023, Номер 25(43), С. 7884 - 7889

Опубликована: Окт. 25, 2023

A visible-light-induced metal-free trifluoromethylselenolation of aryl iodides and bromides with [Me4N][SeCF3] is described. The reaction was conducted at ambient temperature by successfully harnessing the light-sensitive SeCF3 reagent. Mechanistically, EDA complexes between halide -SeCF3 anion or base might be formed excited light, which subsequently undergo intracomplex SET processes to generate •SeCF3 radicals as key intermediates, allowing a convenient green access various trifluoromethyl selenoethers.

Язык: Английский

Процитировано

7

Catalyst-free photoarylation reactions promoted by visible light DOI
Felipe C. Braga, Guilherme M. Martins, Marcelo S. Franco

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(4), С. 1251 - 1275

Опубликована: Дек. 28, 2023

This review presents significant and selected examples of organic synthesis methods that use visible-light-promoted photoarylation reactions without the need for additional photocatalysts.

Язык: Английский

Процитировано

7

Regiospecific deoxygenative deuteration of ketones via HOME chemistry DOI
Ruohua Gui, Chao‐Jun Li

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(7), С. 1767 - 1772

Опубликована: Янв. 1, 2023

A ruthenium-catalyzed deoxygenative deuteration of ketones is developed under mild conditions via HOME chemistry with 91% to 96% deuterium content.

Язык: Английский

Процитировано

6

Visible–Light–Induced Phosphorylation Reaction of α‐Diazoesters with H‐Phosphine Oxides to Construct (Z)‐Phosphinic Hydrazones DOI

Ya‐Ping Feng,

Hongyu Ding,

Ruisheng Liu

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(4)

Опубликована: Фев. 26, 2024

Abstract A convenient visible–light–promoted phosphorylation reaction of α‐diazoesters with H‐phosphine oxides for the preparation ( Z )‐phosphinic hydrazones has been explored. This could be performed under mild conditions to afford a series in moderate good yields through photoisomerization C=N bond.

Язык: Английский

Процитировано

2