Cited by Crafting mono- and novel bis-methylated pyrroloquinoxaline derivatives from a shared precursor and its application in the total synthesis of marinoquinoline A

Visible Light-Induced Reactions of Diazo Compounds and Their Precursors DOI

Ziyan Zhang, Vladimir Gevorgyan

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(11), P. 7214 - 7261

Published: May 16, 2024

In recent years, visible light-induced reactions of diazo compounds have attracted increasing attention in organic synthesis, leading to improvement existing reactions, as well the discovery unprecedented transformations. Thus, photochemical or photocatalytic generation both carbenes and radicals provide milder tools toward these key intermediates for many valuable However, vast majority transformations represent new reactivity modes compounds, which are achieved by decomposition photoredox catalysis. particular, use a redox-active photocatalysts opens avenue plethora radical reactions. The application methods led inaccessible classical associated with metal carbenes. most cases, act sources but can also serve acceptors. Importantly, described processes operate under mild, practical conditions. This Review describes this subfield compound chemistry, particularly focusing on advancements.

Language: Английский

Citations

Visible Light‐Mediated Cyclopropanation: Recent Progress DOI

Ze‐Le Chen,

Yang Xie, Jun Xuan

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(44)

Published: Oct. 21, 2022

Abstract Cyclopropanes are one of the most important strained rings existing in various pharmaceutical products and secondary metabolites. They also widely used total synthesis natural products, medicinal chemistry, materials science. In past years, photochemical cyclopropanation has been gradually developed as a robust attractive synthetic method to prepare diverse cyclopropane backbones. this review, we summarize recent advances visible light‐mediated synthesis, especially using carbene transfer strategy photocatalytic radical reactions.

Language: Английский

Citations

Visible Light-Driven α-Diazoketones as Denitrogenated Synthons: Synthesis of Fluorinated N-Heterocycles via Multicomponent Cyclization Reactions DOI

Peng Zhao, Lingfeng Wang,

Xiaoshuang Guo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(18), P. 3314 - 3318

Published: May 1, 2023

We disclose herein an efficient photochemical formal [3+2+1] annulation strategy for the transformation of diazocarbonyl compounds into various fluorinated nitrogen-containing heterocycles. This is characterized by reacting fluoroalkyl radicals with α-diazoketones, which are used as infrequent denitrogenated synthons under visible light. Moreover, a wide range N-heterocycles containing precious CF3 and perfluoroalkylated groups constructed in moderate to good yields. Notably, this may provide fruitful path synthesis complex organofluorides via diazo/fluorine/radical chemistry.

Language: Английский

Citations

Photocatalytic Synthesis of Indanone, Pyrone, and Pyridinone Derivatives with Diazo Compounds as Radical Precursors DOI

Yang Xie,

Ye‐Peng Bao,

Xiao-Yan Zhuo

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(7), P. 1393 - 1398

Published: Feb. 12, 2024

We disclose herein a photocatalytic radical cascade cyclization of diazoalkanes for the divergent synthesis important carbocycles and heterocycles. Under optimal reaction conditions, various indanone, pyrone, pyridinone derivatives can be obtained in moderate to good yields. Mechanistic experiments support formation carbon-centered radicals from through proton-coupled electron transfer process. Scale-up using continuous flow technology useful downstream application formed heterocycles further render strategy attractive valuable.

Language: Английский

Citations

Photocatalytic Regioselective Difunctionalization of Alkenes with Diazo Compounds and tert-Butyl Nitrite: Access to γ-Oximino Esters DOI

Yantao Liu,

Keyong Zhu,

Jingjing Zhao

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(37), P. 6834 - 6838

Published: Sept. 8, 2022

A visible-light photocatalytic regioselective difunctionalization of alkenes with diazo compounds and tert-butyl nitrite has been developed. The protocol provides an efficient approach to γ-oximino esters under mild conditions. Significantly, this transformation not only shows the good compatibility nucleophilic electrophilic but also displays generating alkyl radicals that preferred addition over nitroso radicals.

Language: Английский

Citations

Eosin Y mediated photo-catalytic C–H functionalization: C–C and C–S bond formation DOI

Dinesh Singla,

Vijay Luxami, Kamaldeep Paul

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(1), P. 237 - 266

Published: Nov. 23, 2022

C–C and C–S bonds are valuable in organic transformation for synthesizing various bioactive heterocycles.

Language: Английский

Citations

Photocatalytic Three-Component Synthesis of 3-Heteroarylbicyclo[1.1.1]pentane-1-acetates DOI

Wenhao Xu,

Zicong Zheng,

Guoxiang Bao

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(22), P. 4050 - 4055

Published: May 26, 2023

Herein, we report a visible-light-induced three-component reaction involving [1.1.1]propellane, diazoates, and various heterocycles for the synthesis of 3-heteroarylbicyclo[1.1.1]pentane-1-acetates. Throughout this reaction, radicals generated from diazoate species react with [1.1.1]propellane in an addition to form bicyclo[1.1.1]pentane (BCP) that subsequently heterocycles, leading formation 1,3-disubstituted BCP acetates. Notably, methodology exhibits excellent functional group compatibility, high atom economy, mild conditions, thus facilitating suitable synthetic access

Language: Английский

Citations

Heterogeneous Photocatalytic C–H Functionalization of Indoles with Diazo Compounds Enabled by Carbon Nitride DOI

Peiying Li, Rong Chang,

Fujun Guan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 8703 - 8708

Published: May 29, 2023

Herein, we reported the heterogeneous photocatalytic C–H alkylation of indoles with diazo compounds using graphitic carbon nitride (g-C3N4) as photocatalyst. The reaction was carried out under a simple operation and mild conditions. In addition, catalyst found to be stable reusable after five cycles. photochemical proceeds via an intermediary radical, which is generated from through visible-light-promoted proton-coupled electron transfer (PCET) process.

Language: Английский

Citations

Visible-Light-Induced Annulation of Iodonium Ylides and 2-Isocyanobiaryls to Access 6-Arylated Phenanthridines DOI

Jinyang Chen, Hongyu Wu,

Hai‐Yang Song

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 8360 - 8368

Published: June 1, 2023

A 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4-CzIPN)-photocatalyzed cascade arylation/cyclization reaction of 2-isocyanobiaryls and iodonium ylides was established for the synthesis 6-arylated phenanthridines. This is first example employing as aryl radical sources in a visible-light-induced cyclization reaction.

Language: Английский

Citations

Visible-light-induced photocatalyst-free activation of alkynyl triflones for trifluoromethylalkynylation of unactivated 1,6-dialkenes DOI

Yonghao Li, Anxiang Huang, Fuyi Zhang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(15), P. 6009 - 6013

Published: Jan. 1, 2023

A visible-light-induced trifluoromethylalkynylation of 1,6-dialkenes was developed under transition-metal-free and photocatalyst-free conditions, enabling the construction three C–C bonds in a single preparation step.

Language: Английский

Citations