Electrochemical difunctionalization of isocyanides by a three-component reaction cascade Mumm rearrangement: rapid access to sulfur-containing imides DOI Creative Commons

Hongmei Jiang,

Zhibin Nong,

Xi Chen

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 1, 2024

Language: Английский

Cyanation with isocyanides: recent advances and perspectives DOI

Yingying Shan,

Xun Zhang,

Gongle Liu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(12), P. 1546 - 1562

Published: Jan. 1, 2024

This review focuses on the cyanation of isocyanides with recent advances and perspectives.

Language: Английский

Citations

11
The Strategies towards Electrochemical Generation of Aryl Radicals DOI
Xiaobao Zeng

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 16, 2024

The advancement in electrochemical techniques has unlocked a new path for achieving unprecedented oxidations and reductions of aryl radical precursors controlled selective manner. This approach facilitates the construction aromatic carbon-carbon carbon-heteroatom bonds. In light green merits growing importance this technique chemistry, review aims to provide an overview recent advance generation radicals organized by precursor type, with focus on substrate scope, limitation, underlying mechanism, thereby inspiring future work generation.

Language: Английский

Citations

11
S-alkyl Dithiocarbamates Synthesis through Electrochemical Multicomponent Reaction of Thiols, Hydrogen Sulfide, and Isocyanides DOI
Xiaoying Liu,

Tian-Cheng Cai,

Mengxue Zhu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(17), P. 12311 - 12318

Published: Aug. 16, 2023

Dithiocarbamates synthesis is extremely important in plenty of biomedical and agrochemical applications, especially fungicide development, but remains a great challenge. In this work, we have successfully developed multicomponent reaction protocol to convert H2S into S-alkyl dithiocarbamates under constant current conditions. No additional oxidants nor catalysts are required, due mild conditions, the reactions display broad substrate scope, including varieties thiols or disulfides.

Language: Английский

Citations

12
Photoinduced radical cyclization reaction of isocyanides with α-carbonyl bromides to access 11-alkyl-substituted 1,4-dibenzodiazepines DOI
Ao-Long Li,

R.-Q. Xie,

Quan Zhou

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A photochemical radical cascade cyclization reaction of isocyanides with α-carbonyl bromides under mild conditions is disclosed for accessing 1,4-dibenzodiazepines, demonstrating good tolerance towards various functional groups.

Language: Английский

Citations

0
Electrochemically Driven Ugi-Azide Reaction via C(sp3)–H Bond Activation of Tertiary Amines DOI
Bin Song, Feng Zhao,

Pengxiang Gao

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(6), P. 1561 - 1567

Published: Jan. 31, 2025

An electrochemically driven Ugi-azide reaction was established via C(sp3)-H bond activation of tertiary amines to prepare α-aminomethyl tetrazoles within 2.5 h under mild conditions with remarkable tolerance various functional groups. Besides, this electrochemical strategy not only obviated the needs iodine, metal, and exogenous oxidant but possessed potential applicability convenient large-scale synthesis. Mechanistic studies indicated both alkyl carbon-centered radical generated at anode intramolecular [3 + 2] cycloaddition are key factors for strategy.

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
Radical Addition to 2-Allenylaryl Isocyanides for the Preparation of 2,3-Difunctionalized Quinolines DOI
Till Drennhaus,

Jens Birschel,

Constantin G. Daniliuc

et al.

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

Published: May 27, 2025

2-Allenylaryl isocyanides are presented as a novel platform to construct quinolines carrying various substituents in positions 2 and 3 via radical addition cyclization cascades. Carbon-, sulfur-, tin-centered radicals add the isonitrile functionality generate corresponding imidoyl radicals, which undergo 6-exo-cyclization onto ortho-allenyl moiety. The newly generated benzylic either reduced or cyanated. In latter case, enantioselective trapping is achieved.

Language: Английский

Citations

0
Iron-catalyzed β-hydroxymethylative carbonylation of styrene under photo-irradiation DOI

Meng Guan,

Ming Hou,

Shuwang Tang

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(89), P. 13309 - 13312

Published: Jan. 1, 2023

This study describes an iron-catalyzed divergent oxidation of styrene into β-hydroxylmethylketone and ketone under photo-irradiation. divergence is ascribed to the use with various substituents. More importantly, methanol oxidized formaldehyde in reaction serves as a C1 synthon. Mechanism investigations show that initiated by oxidative SET transfer cation radical. The pathway undergoes HAT β-hydride elimination well concerted cyclization. Particularly, several drug-like molecules, such melperone analogue, lenperone haloperidol are synthesized. In addition, this method also applicable synthesis natural product (R)-atomoxetine.

Language: Английский

Citations

7
Electrochemically-Driven Difunctionalization of Isocyanide and Mumm Rearrangement Cascade: Expeditious Synthesis of N-acyl-N-alkyl S-thiocarbamates. DOI

Kuldeep Singh Bhati,

Siddharth Sharma

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(57), P. 7355 - 7358

Published: Jan. 1, 2024

A novel electrochemical multicomponent reaction (e-MCR) synthesizes N -substituted S -thiocarbamate derivatives from isocyanides, thiols, and carboxylic acids via a difunctionalization Mumm rearrangement cascade.

Language: Английский

Citations

2
Electrochemical semi-hydrogenation of adiponitrile over copper nanowires as a key step for the green synthesis of nylon-6 DOI Creative Commons

Shutao Wu,

Jia Cheng,

Yang Xiang

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(29), P. 11521 - 11527

Published: Jan. 1, 2024

The electrochemical semi-hydrogenation of ADN to ACN with a Cu NWAs electrode in alkaline media.

Language: Английский

Citations

2