Photoinduced Deconstructive Alkylation Approach Enabled by Oxy-Radicals from Alcohols DOI

Yiman Gao,

Yan Li,

W. B. Yan

и другие.

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

Опубликована: Сен. 13, 2024

Alcohols are the most commercially abundant, synthetically versatile and operationally convenient functional groups in organic chemistry. Therefore, a strategy that utilizes hydroxy-containing compounds to develop novel bond disconnection formation process would achieve molecular diversity. Herein, deconstructive for generation of quinoxalin-2(1H)-one derivatives has been developed from alcohol precursors via oxy-radical-induced β-fragmentation. Additionally, 1,5-HAT deoxygenation by P(III) along with oxy-radical were demonstrated as alternative pathways this transformation. Furthermore, deep-seated reorganization few terpenes carbon framework, unique activity inhibition against growth pathogenic fungi was observed.

Язык: Английский

Metal- and Photocatalyst-Free, Visible-Light-Initiated C3 α-Aminomethylation of Quinoxalin-2(1H)-ones via Electron Donor–Acceptor Complexes DOI
Devidas A. More, Sachin R. Shirsath,

M. Muthukrishnan

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(18), С. 13339 - 13350

Опубликована: Авг. 31, 2023

We report a metal- and photocatalyst-free C3 α-aminomethylation of quinoxalin-2(1H)-ones with N-alkyl-N-methylanilines. The reaction proceeds through the formation photoactivated electron donor–acceptor complex between present method provides mild environmentally friendly protocol that exhibits good atom economy excellent functional group tolerance to obtain library biologically significant α-aminomethylated in yields.

Язык: Английский

Процитировано

13

Selective electrochemical thiocyanation/selenocyanation of C(sp3)-H and C(sp2)-H bonds DOI
Zhihao Wang, Binbin Chen, Qing Pang

и другие.

Molecular Catalysis, Год журнала: 2024, Номер 559, С. 114060 - 114060

Опубликована: Март 21, 2024

Язык: Английский

Процитировано

4

A copper(ii) bromide/NMO system for α-amination of esters under continuous-flow conditions with reduced catalyst loading DOI

Yaman Chauhan,

Kankanala Naveen Kumar,

V. Ravichandiran

и другие.

New Journal of Chemistry, Год журнала: 2024, Номер 48(14), С. 6095 - 6102

Опубликована: Янв. 1, 2024

A new copper( ii ) bromide/ N -methylmorpholine -oxide (NMO)-promoted method for α-amination of esters under continuous-flow conditions, with reduced catalyst loading is reported.

Язык: Английский

Процитировано

3

TEMPO-Mediated Dehydrogenative Hydroxyfluoroalkylation of Arylamines with Polyfluorinated Alcohols DOI

Xiaoyang Gao,

Juting Liao,

Hengyi Wei

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(9), С. 6169 - 6179

Опубликована: Апрель 24, 2024

An efficient 2,2,6,6-tetramethylpiperidinooxy (TEMPO)-mediated hydroxyfluoroalkylation of arylamines with polyfluorinated alcohols via a radical-triggered C(sp

Язык: Английский

Процитировано

3

p-Diarylboryl Halothiophenols as Multifunctional Catalysts via Photoactive Intramolecular Frustrated Lewis Pairs DOI

Takeru Kikura,

Y. B. Taura,

Yoshitaka Aramaki

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(29), С. 20425 - 20431

Опубликована: Июль 8, 2024

p-Diarylboryl halothiophenols are developed and unequivocally characterized. Their photophysical properties catalytic performance unveiled by experimental theoretical investigations. This novel class of triarylboranes behaves as a Brønsted acid to generate the corresponding borylthiophenolate that can absorb visible light undergo intramolecular charge transfer form radical pair consisting boron anion thiyl radical, which acts single-electron reductant while engaging in hydrogen atom regenerate parent borylthiophenol. The synthetic relevance this mode action is demonstrated establishment unique catalysis integrates three different yet tunable functions single cycle, thereby allowing borylthiophenols solely promote assembly sterically congested 1,2-diols 1,2-aminoalcohol derivatives via radical–radical cross-coupling.

Язык: Английский

Процитировано

3

Access to quaternary-carbon-containing β-alkyl amides via persulfate-promoted domino alkylation/smiles rearrangement of alkenes DOI Creative Commons
Xiaohu Yang, Xiaoqing Wan, Wenchao Yang

и другие.

RSC Advances, Год журнала: 2025, Номер 15(20), С. 16183 - 16186

Опубликована: Янв. 1, 2025

An efficient radical alkylative annulation/arylation of N -(arylsulfonyl)acrylamide with 4-alkyl-1,4-dihydropyridines (DHP) was developed for synthesizing all-carbon quaternary-centered β-alkyl amides.

Язык: Английский

Процитировано

0

Synthesis of Heterocycles from 2‐Acylbenzoic Acids DOI
Yufeng Liu, Li Cui, Guo‐Ping Yang

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(27)

Опубликована: Июнь 8, 2023

Abstract Heterocyclics are the crucial scaffolds present in pharmaceuticals, natural products, biologically active compounds and agrochemicals. Consequently, development of simple practical methods for constructing heterocyclics has always been a fascinating field organic synthesis. Recently, 2‐acylbenzoic acids, highly reactive versatile synthons, have broadly applied construction heterocycles due to their multiple reaction sites. In this review, we summarized recent progress application acids synthesis including phthalides, isochromanones, isoindolines, phthalazinones, quinolones. The substrate scopes, proposed mechanisms, product different types reactions discussed.

Язык: Английский

Процитировано

8

Photoinduced Metal‐Free Decarboxylative Fluoroalkylation of Alkenes for the Synthesis of N‐Arylbutanamides and Oxindoles DOI

Yi‐Gang Ji,

Z. Li,

Yuqing Yang

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(68)

Опубликована: Авг. 28, 2024

The visible light-induced decarboxylative cascade reaction of fluoroalkyl carboxylic acids has been achieved for the efficient synthesis fluorinated compounds. However, most transformations rely on noble iridium metal complex. Herein, a metal-free realized. This protocol features simple operation, transition free, and good functional group tolerance.

Язык: Английский

Процитировано

2

Iron-Catalyzed Synthesis of Peroxylpyrrolo[2,1-a]isoquinolines through Oxidative Dearomatization DOI
Xiang Huang,

An-Ni Yu,

De He Yang

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(21), С. 15326 - 15334

Опубликована: Окт. 25, 2023

A mild late-stage modification of pyrrolo[2,1-a]isoquinolines was established through iron-catalyzed oxidative dearomatization and peroxidation. Peroxylated pyrroloisoquinolines have been prepared readily with hydroperoxide in low to good yields (up 72%) at room temperature. Interestingly, the treatment fully aromatized pyrrolo[1,2-a]quinolines under current reaction system resulted formation ring-opening products.

Язык: Английский

Процитировано

5

Visible-Light-Driven α-C(sp3)–H Bond Functionalization of Glycine Derivatives DOI Open Access

Yao Tian,

Xiubin Bu,

Yuanrui Chen

и другие.

Catalysts, Год журнала: 2023, Номер 13(12), С. 1502 - 1502

Опубликована: Дек. 8, 2023

The glycine motif is widely prevalent in bioactive peptides. Thus, the direct and precise modification of derivatives has attracted significant attention over past few decades. Among various protocols for derivatives, visible-light-driven α-C(sp3)–H bond functionalization emerged as a powerful tool to achieve this objective, owing its merits atom economy, selectivity, reaction simplicity, sustainability. This review summarizes recent advancements derivatives. contents are organized based on photocatalysts employed modes process. mechanism, challenges encountered, future trends also discussed, enabling readers understand current developmental status field.

Язык: Английский

Процитировано

5