Catalyst-free synthesis of hydrazino-containing glycine derivatives via a diaziridine in-situ formation/ring-opening cascade DOI

Chang-Long Rong,

Qiang‐Qiang Li, Jun Xuan

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(16), P. 9104 - 9109

Published: Jan. 1, 2024

A green and efficient method for the synthesis of glycine derivatives from amines, azodicarboxylates, diazoalkanes has been developed. This multicomponent reaction occurred under mild conditions in absence any catalysts or additives.

Language: Английский

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

59
Visible light-mediated photolysis of organic molecules: the case study of diazo compounds DOI
Rafael D. C. Gallo, Guilherme Cariello Silva, Tales A. C. Goulart

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(48), P. 7346 - 7360

Published: Jan. 1, 2023

This article discusses the photochemistry of several diazo compounds undergoing visible light-mediated photolysis to generate free carbenes (or other highly reactive intermediates), which can be sequentially trapped by different reacting partners.

Language: Английский

Citations

45
Recent advances in combining photo- and N-heterocyclic carbene catalysis DOI Creative Commons
Xiaochen Wang,

Senhui Wu,

Rongxin Yang

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(46), P. 13367 - 13383

Published: Jan. 1, 2023

This review summarizes recent advances in combining photo- and N-heterocyclic carbene catalysis, as well provides an outlook on future opportunities challenges.

Language: Английский

Citations

43
Visible-Light-Induced [4 + 3]-Annulation of Carbonyl Ylides with Alkenyl Pyrazolinone for Constructing [4.2.1]-Oxo-Bridged Oxocine Skeleton DOI

Dong-Sheng Ji,

Xin Zhang,

Peiqin Zhang

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: 27(2), P. 709 - 714

Published: Jan. 7, 2025

Herein, we present a visible-light-induced protocol for the synthesis of highly functionalized oxo-bridged oxocine skeletons. This method generates carbenes via ortho-acyl diazo compounds, which are rapidly intercepted by oxygen atom an intermolecular acyl group to form cyclic 1,3-dipole. The in situ generated reactive 1,3-dipole undergoes facile formal [4 + 3] cycloaddition with alkenyl pyrazolinone, yielding [4.2.1]-oxo-bridged compounds.

Language: Английский

Citations

2
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

39
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

39
Visible photons as ideal reagents for the activation of coloured organic compounds DOI Creative Commons
Lorenzo Di Terlizzi, Luca Nicchio,

Stefano Protti

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(10), P. 4926 - 4975

Published: Jan. 1, 2024

In search for the perfect wave(length). This review is dedicated to recent efforts in development of visible light driven photochemical strategies occurring coloured organic compounds.

Language: Английский

Citations

11
Comparative study of Mg/Al-LDH and Mg/Fe-LDH on adsorption and loss control of 2,4-dichlorophenoxyacetic acid DOI Creative Commons
Zeyuan Zhang,

Liangjie Tang,

Jing Luo

et al.

Advanced Biotechnology, Journal Year: 2025, Volume and Issue: 3(1)

Published: Jan. 21, 2025

Low efficiency and high surface runoff of 2,4-dichlorophenoxyacetic acid (2,4-D) from agricultural field threaten crop yield severely. Layered double hydroxides (LDH) have shown promising adsorption properties for 2,4-D. However, the comparison two environmentally friendly LDHs (i.e. Mg/Al-LDH vs Mg/Fe-LDH) on 2,4-D corresponding intrinsic mechanisms are still unclear, studies leaching control by in soil environment particularly limited. In this study, Mg/Fe-LDH were selected to conduct their kinetics experiment combined with characterization technology. The results showed that capacity was up 242 mg kg-1 64 kg-1, respectively, which negatively correlated pH. Adsorption both dominated chemical adsorption, including electrostatic attraction inner sphere complexation, but no interlayer mechanism. contains smaller metal ion radius, provides greater charge density, resulting complexation compared Mg/Fe-LDH. driven higher energy (Eads) lower electron as corroborated density functional theory (DFT) calculation. column further verified could loss more effectively, amount be significantly reduced 61.7%, while effect only 24.2%. This study theoretical guidance screening potential LDH types solve improve its effectiveness production.

Language: Английский

Citations

1
Enantioselective Photochemical Carbene Insertion into C–C and C–H Bonds of 1,3-Diketones by a Guanidine-Amide Organocatalyst DOI
Shiyang Li,

Cefei Zhang,

Guihua Pan

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(7), P. 4656 - 4666

Published: March 22, 2023

A visible-light-induced enantioselective free carbene transfer reaction of α-diazoesters with 1,3-diketones is established by utilizing a chiral bifunctional guanidine-amide organocatalyst. Selective insertion into the C–C or C–H bonds 1,3-diketone could be achieved bearing different steric hindrances. The transformations enable preparation series 1,4-diketones quaternary carbon center 2-substituted-1,3-diketones in good enantioselectivities. On basis control experiments and DFT calculation, stepwise triplet coupling pathway suggested. possible mechanism proposed to explain origin high enantioselectivities via hydrogen-bonds electrostatic interactions catalyst.

Language: Английский

Citations

20
Emerging progress: photochemical transformation of nitroso compounds DOI

Ze‐Le Chen,

Qiangqiang Li, Armido Studer

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: July 17, 2024

Language: Английский

Citations

6