Synthesis of Aminated C-3 Aryloylated Benzofuran, Furopyridine, Benzothiophene, and Indole Derivatives from 1,6-Enyne and N-Aminopyridinium Salt in Visible Light DOI

Shruti Rajput,

Rajat,

Nitesh

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 20, 2024

We report a visible-light-assisted tandem oxidative 5-

Язык: Английский

Recent Advances in Cyclization Reactions of 1,6‐Enynes DOI

J.H. Liu,

Sheng‐Qi Xu,

Yaping Han

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(6), С. 1220 - 1268

Опубликована: Янв. 22, 2024

Abstract Elaborated molecular architectures, specifically those bearing one or more carbon stereocenters, stand as an important class of carbocyclic and heterocyclic frameworks because they are frequently occurring core structures in numerous natural products biologically active pharmaceutical molecules. Over the past few decades, development versatile synthetic approaches via cascade cyclization reactions 1,6‐enynes for construction a series fused spiro compounds has been focus great deal research initiatives. These synthesis strategies peculiarly fascinating context assembly wide array molecules, products, agrochemicals, functional materials. In this review, recent developments transformations with diverse coupling reagents summarized since 2018, which could be divided into five categories: 1) Introduction; 2) Transition metal catalyzed 1,6‐enynes; 3) Metal‐free 4) Visible‐light‐induced 5) Electrocatalytic 1,6‐enynes.

Язык: Английский

Процитировано

13

Radical cascade cyclization of 1,n-enynes under photo/electrochemical conditions DOI

Zhenzhi Cai,

Sven Trienes, Kairui Liu

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(22), С. 5735 - 5745

Опубликована: Янв. 1, 2023

During the past decade, photo- and electrochemical reactions proceeding via single-electron-transfer (SET) triggered radical pathways have emerged as an indispensable strategy for efficient formation of chemical bonds.

Язык: Английский

Процитировано

20

Visible‐Light‐Driven Cyclizations DOI Creative Commons
Emilia Oueis, Mirella Elkadi, Ramón Rios

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(4), С. 635 - 697

Опубликована: Янв. 13, 2024

Abstract In recent years, the interest to develop cyclizations promoted by visible light has been gaining a lot of attention due its sustainability aspect. this review, we summarize most important advances in period describing methods used generate different ring sizes, while focusing on mechanistic details these reactions.

Язык: Английский

Процитировано

8

Visible Light‐Induced Metal‐Free Fluoroalkylations DOI

Cheol Hyeon Ka,

Seoyeon Kim,

Eun Jin Cho

и другие.

The Chemical Record, Год журнала: 2023, Номер 23(9)

Опубликована: Март 21, 2023

Abstract Fluoroalkylation is a crucial synthetic process that enables the modification of molecules with fluoroalkyl groups, which can enhance properties compounds and have potential applications in medicine materials science. The utilization visible light‐induced, metal‐free methods particular importance as it provides an environmentally friendly alternative to traditional eliminates risks associated metal‐catalyst toxicity. This Account describes our studies on fluoroalkylation processes, include use organic photocatalysts or EDA complexes. We utilized organophotocatalysts such Nile red, tri(9‐anthryl)borane, indole‐based tetracyclic complex, well catalyst‐free chemistry through photoactive halogen bond formation unconventional transient ternary complex nucleophilic source. A variety π‐systems including arenes/heteroarenes, alkenes, alkynes been successfully fluoroalkylated under developed reaction conditions.

Язык: Английский

Процитировано

15

Electron Donor‐Acceptor Complex Driven Photocatalyst‐Free Trifluoromethylation of Heterocycles DOI
Yufei Li,

Jie Hou,

Pei Zhang

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(31)

Опубликована: Апрель 1, 2024

Heterocyclic trifluoromethylation is efficiently initiated through a photochemical reaction utilizing an electron donor-acceptor (EDA) complex, proceeding smoothly without the use of photocatalysts, transition-metal catalysts, or additional oxidants. This method has been optimized extensive experimentation, demonstrating its versatility and efficacy across various substrates, including quinoxalinones, coumarins, indolones. Notably, this approach enables practical synthesis trifluoromethylated quinoxalinones on gram scale. Mechanistic investigations that incorporate radical trapping ultraviolet/visible spectroscopy, confirmed formation EDA complex elucidated pathways. study highlights crucial role photoactivation in trifluoromethylation, significantly expanding application scope complexes chemical synthesis.

Язык: Английский

Процитировано

5

Visible Light-Induced Radical Cascade Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF2H-Substituted Polycyclic Imidazoles DOI Creative Commons
S.J. Lin, Yuanyuan Deng,

Hanxun Zhong

и другие.

ACS Omega, Год журнала: 2024, Номер 9(26), С. 28129 - 28143

Опубликована: Июнь 19, 2024

An efficient and mild protocol for the visible light-induced radical cascade difluoromethylation/cyclization of imidazoles with unactivated alkenes using easily accessible bench-stable difluoromethyltriphenylphosphonium bromide as precursor -CF

Язык: Английский

Процитировано

5

Iodine radical mediated cascade [3 + 2] carbocyclization of ene-vinylidenecyclopropanes with thiols and selenols via photoredox catalysis DOI Creative Commons
Zhe Meng, Min Shi, Yin Wei

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(5), С. 1395 - 1403

Опубликована: Янв. 1, 2024

A iodine radical mediated cascade [3 + 2] carbocyclization of ene-vinylidenecyclopropanes with thiols and selenols to provide sulfur- or selenium-containing derivatives has been disclosed.

Язык: Английский

Процитировано

4

Copper‐catalyzed radical‐induced annulation‐halo(bi)cyanomethylation of indole‐tethered 1,6‐enynes toward pyrrolo[1,2‐a]indoles DOI
Hang‐Dong Zuo,

Ya‐Yu Yuan,

Xi Chen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(17), С. 3578 - 3584

Опубликована: Июнь 18, 2024

Abstract A copper‐catalyzed radical‐induced annulation‐halocyanomethylation of indole‐linked 1,6‐enynes has been established using haloacetonitrile as radical precursors, enabling the synthesis 21 cyanomethylated pyrrolo[1,2‐ a ]indoles with yields ranging from 42% to 81% and Z / E ratio up 19:1. Moreover, by adjusting reaction temperature, variation annulation‐bromobicyanomethylation process was achieved, resulting in production 12 bicyanomethylated ]indole isomers 41–68%. The stereoisomeric mixture products could be purified their pure configurations through recrystallization. proposed mechanism formulated series control experiments.

Язык: Английский

Процитировано

4

Catalyst‐free visible light‐induced N‐N bond cleavage for the synthesis of iminophosphorane using triarylphosphine and N‐sulfonyl and N‐acylaminopyridinium salt DOI Open Access

Xiaotao Qin,

Chenglei Yang,

Yinjiang Xue

и другие.

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

Опубликована: Фев. 1, 2025

Abstract Herein, we explore a visible light‐enabled radical addition for the construction of N‐sulfonyl and N‐acyliminophosphorane using triarylphosphine N‐acylaminopyridinium salts in absence transition metal, photocatalyst, oxidant or base. This method employs PAr 3 as both reaction catalyst to promote generation amidyl via N−N bond cleavage salts, materials preparation products. transformation exhibits abroad substrate scope good functional group compatibility.

Язык: Английский

Процитировано

0

Vanadium-Catalyzed Trifluoromethylation/Cyclization of Alkenes and 1,7-Enynes with Togni-II Reagent to Access Trifluoromethylated Oxindoles, Isoquinoline-1,3-diones, and Indeno[1,2-c]quinolines DOI
Lei Zhang, Mengdi Liu,

Jin-Jin Zhao

и другие.

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

Опубликована: Май 28, 2025

A vanadium-catalyzed radical cascade trifluoromethylation/(bi)cyclization of alkenes and 1,7-enynes with Togni-II reagent for the synthesis trifluoromethylated oxindoles, isoquinoline-1,3-diones, indeno[1,2-c]quinolines has been developed. These transformations show broad substrate compatibility high regioselectivity. Mechanistic studies reveal that a CF3 is in situ generated to trigger ensuing 5-exo 6-exo cyclization, as well 6-exo/5-endo bicyclization processes.

Язык: Английский

Процитировано

0