Anode material determined divergent 5‐<i>exo</i>‐<i>dig</i> cyclization of <i>N</i>‐cyano‐2‐halobenzamides toward 3‐iminoisoindolin‐1‐ones and 3‐aminoisoindolin‐1‐ones DOI Open Access
Xiaoqing Xie,

Zi-Qiong Li,

Wei Zhou

et al.

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

Published: Nov. 6, 2024

Abstract Herein, an electroreductive aryl radical enabled 5‐ exo ‐ dig cyclization of N ‐cyano‐2‐halobenzamides is presented, providing a convenient route for the synthesis variety 3‐iminoisoindolin‐1‐ones in 30–75% yields. Simply by employing zinc plate instead graphite rod anode, products electrosynthesis are switched to diverse 3‐aminoisoindolin‐1‐ones through aryl‐radical‐mediated and subsequent reductive hydrogenation. Furthermore, this anode material determined divergent features mild electrochemical conditions, excellent substrate scopes, good functional group tolerance.

Language: Английский

Dearomative 1,4-Difunctionalization of Non-Activated Arenes Enabled by Boryl Radical-Mediated Halogen-Atom Transfer DOI
Chengliang Deng, Hao Wu,

Sheng Li

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 1294 - 1304

Published: Jan. 7, 2025

Given the widespread presence of spirocyclic scaffolds in natural products and pharmacologically relevant synthetic compounds, development efficient methodologies for their construction holds great importance medicinal chemistry pharmaceutical research. In this study, a general photochemical dearomative spirocyclization nonactivated arenes has been established. The key to method lies ability amine-borane radicals activate aryl bromides iodides via halogen-atom transfer, thereby allowing conversion halides into corresponding subsequent chemodivergent transformations. remarkable compatibility versatility 1,4-difunctionalization is showed by rapid assembly structurally diverse 1,4-cyclohexadiene-based spirocycles incorporating oxindole, indoline, or dihydrobenzofuran subunits. Moreover, potential utility protocol exemplified formal total synthesis vasopressin V2 receptor antagonist Satavaptan.

Language: Английский

Citations

1
Direct C(sp3)-H functionalization with aryl and alkyl radicals as intermolecular hydrogen atom transfer (HAT) agents DOI
Jia‐Lin Tu, Binbin Huang

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Recent years have witnessed the emergence of direct intermolecular C(sp

Language: Английский

Citations

7
Electrochemically Enabled Synthesis of Multi-substituted Pyrazoles via a Radical Cyclization Cascade DOI

Wan‐Jie Wei,

Y. M. Zeng,

Xianfeng Liang

et al.

Green Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

We have developed a mild and efficient electrochemical reduction approach employing aryl diazonium salts as dual synthons to synthesize valuable multi-substituted pyrazoles for the first time.

Language: Английский

Citations

0
Electrochemical Difunctionalization of Alkenes DOI Open Access

Yin Zhang,

Zilong Zhou,

Jin‐Heng Li

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 3, 2025

Abstract Owing to their wide utilizations in synthesis and products prevalence numerous natural products, pharmaceuticals functional materials, the alkene difunctionalization methods for selective transformations of olefins are important have attracted much attention form synthetic chemists. Among them, electrochemical reaction is particularly promising has becoming a potent sustainable tool alkenes into vicinal difunctionalized structures organic through simultaneous incorporation two groups. Herein, we summarize recent progress reactions according types as well category radicals over past five years. By selecting remarkable examples, elaborately discussed substrate scope mechanisms olefin reaction.

Language: Английский

Citations

0
Synthesis of 2-Organoselenyl Quinolines via Electro-Oxidative Selenocyclization of Isocyanides DOI
Peng‐Fei Huang,

Jia-Le Fu,

Zhi-Gang Quan

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 12, 2025

Organoselenium compounds and quinolines are widely used in drugs materials. Herein, we report an electro-oxidative cyclization between isocyanides diselenides to effectively synthesize 2-organoselenyl a simple undivided cell without transition-metal catalysts or toxic oxidants. Gram-scale synthesis postsynthetic modifications highlighted the practicality of this electrochemical strategy. A series produced with up 82% yield, good functional group tolerance high atom efficiency under room temperature.

Language: Английский

Citations

0
Photoredox Radical Cyclization of o-Vinylaryl Isocyanides and Aryldiazonium Tetrafluoroborates for the Synthesis of 2,4-Disubstituted Quinolines DOI
Min Gao, Chuan Ding, Peng‐Fei Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 23, 2025

Quinolines, a significant part of nitrogen-containing heterocycles, are widely found in functional compounds. Herin, photochemical radical cyclization reaction o-vinylaryl isocyanides and aryldiazonium tetrafluoroborates, has been reported to build 2,4-diaryl quinolines. Readily accessible aryl diazonium salts were utilized as precursors at room temperature. This approach allowed good group tolerance substrate applicability.

Language: Английский

Citations

0
Electrochemical Deaminative Carboxylation of Aryltriazenes with CO2 to Aryl Carboxylic Acids DOI
Lan Zhao,

An‐Guo Wu,

Hongru Li

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 18, 2025

The utilization of CO2 as an appealing chemical feedstock for diverse synthetically valuable products is constantly evolving, potentially alleviating production that relies on petrochemistry. Herein we report the first example electrochemical deaminative carboxylation aryltriazenes with CO2. reaction can be performed under mild and catalyst-free conditions by using sustainable methods a green C1 building block, efficiently converting range readily available into carboxylic acids. In particular, formation C-C bonds would impactful addition to synthesis toolbox.

Language: Английский

Citations

0
Electrochemically Driven Denitrative Cyanation of Nitroarenes DOI
Yiyi Chen,

Qisheng Chen,

Shuangquan Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7555 - 7559

Published: Sept. 3, 2024

A practical denitrative cyanation of feedstock nitroarenes under mild and transition metal-free reaction conditions has been developed. The key to success lies in the use electrochemically driven, inexpensive ionic liquid

Language: Английский

Citations

1
Anode material determined divergent 5‐<i>exo</i>‐<i>dig</i> cyclization of <i>N</i>‐cyano‐2‐halobenzamides toward 3‐iminoisoindolin‐1‐ones and 3‐aminoisoindolin‐1‐ones DOI Open Access
Xiaoqing Xie,

Zi-Qiong Li,

Wei Zhou

et al.

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

Published: Nov. 6, 2024

Abstract Herein, an electroreductive aryl radical enabled 5‐ exo ‐ dig cyclization of N ‐cyano‐2‐halobenzamides is presented, providing a convenient route for the synthesis variety 3‐iminoisoindolin‐1‐ones in 30–75% yields. Simply by employing zinc plate instead graphite rod anode, products electrosynthesis are switched to diverse 3‐aminoisoindolin‐1‐ones through aryl‐radical‐mediated and subsequent reductive hydrogenation. Furthermore, this anode material determined divergent features mild electrochemical conditions, excellent substrate scopes, good functional group tolerance.

Language: Английский

Citations

0