Electrochemical Synthesis of 4‐Selenylated Oxazolones via Oxyselenylation of Ynamides DOI Open Access
Jinhui Cai,

Kaili Cen,

Weishuang Li

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 19, 2024

Abstract Electrosynthesis of selenylated‐oxazolone derivatives via cascade selenylation/cyclization ynamides was disclosed. A series diaryl diselenides, dialkyl and heteroaryl‐substituted tolerated in this protocol delivered 4‐selenyloxazolones 28–83% yields. The scale‐up reaction the oxidation performed to showcase practicability method. Furthermore, mechanistic experiments indicated that a cationic pathway instead radical probably involved.

Language: Английский

Visible-light-induced cyclization of cyclic N-sulfonyl ketimines to N-sulfonamide fused imidazolidines DOI
Xiaotong Wang,

Anzai Shi,

Xianqiang Huang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(18), P. 3798 - 3802

Published: Jan. 1, 2022

A visible-light-induced metal-free cascade cyclization of cyclic N-sulfonyl ketimines with N-arylglycines for the construction N-sulfonamide-fused imidazolidines was developed. The procedure employed 3 mol% eosin Y as photocatalyst at room temperature under visible light irradiation, providing various in good yields (32 examples, up to 86% yields).

Language: Английский

Citations

17

Radical annulation of a designed diene system: access to nitro-benzo[b]azepines DOI
Kai Sun, Yan Zhang, Miao Tian

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(69), P. 9658 - 9661

Published: Jan. 1, 2022

Herein, we describe a novel O2N˙-triggered ordered addition 7-endo cyclization reaction with excellent chemo- and regioselectivity. With such strategy, structurally diverse nitro-benzo[b]azepines were prepared 28 examples. Large-scale operation handy N-Ts N-Cbz deprotection reveal the promising utility of this methodology. Mechanistic studies suggest that proceeds through radical pathway.

Language: Английский

Citations

14

Visible-Light-Mediated (sp3)Cα–H Functionalization of Ethers Enabled by Electron Donor–Acceptor Complex DOI Creative Commons
Sourav Roy, Indranil Chatterjee

ACS Organic & Inorganic Au, Journal Year: 2022, Volume and Issue: 2(4), P. 306 - 311

Published: March 29, 2022

A synthetically beneficial visible-light-mediated protocol has been disclosed to achieve C–H amination of readily available feedstocks cyclic and acyclic ethers. rarely identified N-bromosuccinamide–tetrahydrofuran electron donor–acceptor complex served as an initiator functionalize both α-diazoketones dialkyl azodicarboxylates. This developed methodology gives alternative milder way construct the C–N bond can be explored for formation C–C perform arylation allylation reactions.

Language: Английский

Citations

13

Photo/Electrochemical‐Mediated C(sp3)−H Bond Functionalization of (Thio)Ethers DOI

Lianglong Sun,

Dongyang Zhao, Kai Sun

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(17)

Published: March 11, 2024

Abstract Molecules containing ether skeletons are widely present in drugs, natural products, functional materials, and life science. Direct C(sp 3 )−H bond functionalization is considered a powerful strategy for the construction of novel derivatives. Photo‐/electro‐chemical technology relatively green sustainable synthesis method, which opens up broad application prospect field direct bonds. In recent years, photo‐/electro‐mediated alkylation, arylation, alkynylation, esterification, mercaptoylation, sulfidation, amination ethers have been extensively studied. this review, research progress compounds from 2014 to 2023 systematically reviewed, scope, limitations, mechanisms some reactions discussed.

Language: Английский

Citations

2

Alkane functionalization: Recent advances DOI
Nuno Reis Conceição, Kamran T. Mahmudov⧫, M. Fátima C. Guedes da Silva

et al.

Coordination Chemistry Reviews, Journal Year: 2024, Volume and Issue: 522, P. 216175 - 216175

Published: Sept. 13, 2024

Language: Английский

Citations

2

Selectfluor-mediated construction of 3-arylselenenyl and 3,4-bisarylselenenyl spiro[4.5]trienones via cascade annulation of N-phenylpropiolamides with diselenides DOI
Jinwei Yuan, Qian Chen,

Wen-Tao Wu

et al.

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(19), P. 9451 - 9460

Published: Jan. 1, 2022

A cascade annulation of N -phenylpropiolamides with diselenides leading to the construction 3-arylselenenyl spiro[4.5]trienones was realized under mild conditions Selectfluor as sole oxidant.

Language: Английский

Citations

11

Ni and Fe catalyzed cascade radical reactions of oxime esters with diselenides DOI

Linpeng Liu,

Yanyu Jian,

Weigao Hu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(13), P. 3480 - 3485

Published: Jan. 1, 2022

A radical cyclization and ring-opening of oxime esters with diselenides was developed.

Language: Английский

Citations

10

Electro-Oxidative C3-Selenylation of Pyrido[1,2-a]pyrimidin-4-ones DOI Creative Commons
Jianwei Shi,

Zhichuan Wang,

Xiaoxu Teng

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(5), P. 2206 - 2206

Published: Feb. 27, 2023

In this work, we achieved a C3-selenylation of pyrido[1,2-a]pyrimidin-4-ones using an electrochemically driven external oxidant-free strategy. Various structurally diverse seleno-substituted N-heterocycles were obtained in moderate to excellent yields. Through radical trapping experiments, GC-MS analysis and cyclic voltammetry study, plausible mechanism for selenylation was proposed.

Language: Английский

Citations

6

Palladium-catalyzed distal selective C–H chalcogenation of biphenyl amines DOI
Yunhao Zhou, Tao Zheng, Yue Xu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(53), P. 8262 - 8265

Published: Jan. 1, 2023

A palladium-catalyzed distal C(sp2)-H chalcogenation of biphenyl amines is described. This protocol demonstrates scalability, excellent chemo- and regio-selectivity, broad functional group tolerance, providing efficient access to valuable aryl chalcogenides. Notably, the chalcogenated could be further transformed 8-membered N, Se(S)-heterocycles through copper-catalyzed intramolecular C-N cyclization.

Language: Английский

Citations

6

SCF3 Radical Initiated Cascade Reaction of Unsaturated Hydrocarbon DOI Open Access

Shi Yun,

Ting Xiao,

Dong Xia

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 42(9), P. 2715 - 2715

Published: Jan. 1, 2022

Fluorinated compounds have been widely used in pharmaceuticals, pesticides and other disciplines due to their special physical chemical properties, which motivates the frequent introduction of fluorinated functionalities into lead improve properties.The trifluoromethylthio (SCF3) group with high electronegativity lipophilicity plays an important role a multitude compounds.The recent progress field cascade reaction unsaturated hydrocarbon initiated by SCF3 radical, including design, mechanism outlook, is summarized.

Language: Английский

Citations

8