Reassembly of Unsaturated C–C Bonds by a Cutting/Insertion Cascade DOI
Yaojia Jiang, Ying Xu, Ling Li

et al.

Synlett, Journal Year: 2022, Volume and Issue: 34(04), P. 293 - 300

Published: Nov. 20, 2022

Abstract The reassembly of unsaturated C–C bonds has attracted widespread attention from synthetic chemists due to its advantages unique reactivity, easy handling, and high atom step economies. We recently explored a cutting/insertion cascade as means introducing new C1 source constructing functionalized 1,4-keto aldehyde 2H-furan derivatives through cyclopropanation enamines with various carbene precursors subsequent ring-opening reactions in situ. Aminocyclopropanes are believed be involved key intermediates these transformations. This Synpacts article outlines our recent contributions this increasingly important research area. 1 Introduction 2 Cleavage Enamine C=C Double Bonds Hydrolysis 1,4-Keto Aldehydes 3 Cyclization 2H-Furans 4 Ynone/Ynoate C≡C Triple 5 Conclusion

Language: Английский

Recent advances in visible light-mediated chemical transformations of enaminones DOI
Yu Han,

Liyun Zhou,

Chengyu Wang

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 108977 - 108977

Published: Aug. 26, 2023

Language: Английский

Citations

63
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

60
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

48
Iodine-Promoted Thioylation and Dicarbonylation of Enaminone α-C Sites: Synthesis of Fully Substituted Thiazoles via C═C Bond Cleavage DOI
Peng Zhao, You Zhou, Can Wang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2505 - 2515

Published: Feb. 5, 2024

A novel iodine-promoted difunctionalization of α-C sites in enaminones was demonstrated as a means synthesizing variety fully substituted thiazoles by constructing C–C(CO), C–S, and C–N bonds. This transformation allows the realization unusual aryl C2 synthons simultaneously thioylation dicarbonylation sites. preliminary mechanistic study performed indicated that cleavage C═C bonds involves bicyclization/ring-opening oxidative coupling sequence.

Language: Английский

Citations

14
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

12
Recent progress in visible light‐driven halogenation: Chlorination, bromination, and iodination DOI

Anh Thu Nguyen,

Houng Kang, Truong Giang Luu

et al.

Bulletin of the Korean Chemical Society, Journal Year: 2024, Volume and Issue: 45(9), P. 738 - 758

Published: Sept. 1, 2024

Abstract Halogenation is one of the most important transformations in organic synthesis. Halogenated compounds are employed many reactions to prepare useful molecules. Many methods have been developed introduce halogens into different compounds. Visible light‐mediated efficient, low‐toxic, and mild‐condition applied for various chemistry transformations. Remarkably, there has an increasing development application visible light‐induced halogenation recent years. Herein, we present a comprehensive summary including chlorination, bromination, iodination under light irradiation since 2020.

Language: Английский

Citations

5
Catalyst-Free Photoinduced C–C Bond Formations DOI
Shyamal Kanti Bera, Rosalin Bhanja, Prasenjit Mal

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(10), P. 1467 - 1486

Published: Feb. 27, 2023

Abstract Use of sustainable energy sources in synthetic organic chemistry has become one the most popular research topics due to environmental pollution and global warming. In this review, we discuss photocatalyst-free transition-metal-free light-induced reactions for construction carbon–carbon (C–C) bonds. The reaction systems discussed here are C–C bond formation via carbene intermediates, radical miscellaneous cyclization. 1 Introduction 2 Bond Formation Carbene Intermediates 3 Radical 4 Miscellaneous Cyclization 5 Conclusion

Language: Английский

Citations

12
FeCl3-catalyzed oxidative amidation of benzylic C–H bonds enabled by a photogenerated chlorine-radical DOI
Yingying Yang, Xianglin Yu, Na He

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(68), P. 10299 - 10302

Published: Jan. 1, 2023

Herein, we report the development of iron-catalyzed benzylic C-H oxidative amidation reactions via photoinduced ligand-to-metal charge transfer (LMCT). These exhibit a broad substrate scope (60 examples) and offer operationally simple, scalable procedures for accessing valuable products from methylarenes in single step. Mechanistic studies control experiments confirm participation photogenerated chlorine radical facilitating hydrogen atom (HAT) bond to initiate reaction.

Language: Английский

Citations

11
Rh-Catalyzed Enantioselective Synthesis of Acyclic Quaternary Carbons via Carbene Insertion DOI
Kun He,

Weikun Zeng,

Yingcheng Wang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 5273 - 5282

Published: March 13, 2025

Language: Английский

Citations

0
Reassembly of Unsaturated C–C Bonds by a Cutting/Insertion Cascade DOI
Yaojia Jiang, Ying Xu, Ling Li

et al.

Synlett, Journal Year: 2022, Volume and Issue: 34(04), P. 293 - 300

Published: Nov. 20, 2022

Abstract The reassembly of unsaturated C–C bonds has attracted widespread attention from synthetic chemists due to its advantages unique reactivity, easy handling, and high atom step economies. We recently explored a cutting/insertion cascade as means introducing new C1 source constructing functionalized 1,4-keto aldehyde 2H-furan derivatives through cyclopropanation enamines with various carbene precursors subsequent ring-opening reactions in situ. Aminocyclopropanes are believed be involved key intermediates these transformations. This Synpacts article outlines our recent contributions this increasingly important research area. 1 Introduction 2 Cleavage Enamine C=C Double Bonds Hydrolysis 1,4-Keto Aldehydes 3 Cyclization 2H-Furans 4 Ynone/Ynoate C≡C Triple 5 Conclusion

Language: Английский

Citations

1