Visible-light-driven Net-1,2-Hydrogen Atom Transfer of Amidyl Radicals to Access β-Amido Ketone Derivatives DOI Creative Commons
Yonggang Jiang, Hui Li,

H. Tang

et al.

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

Published: Dec. 3, 2024

Hydrogen atom transfer (HAT) processes provide an important strategy for selective C-H functionalization. Compared with the popularity of 1,5-HAT processes, however, net-1,2-HAT reactions have been reported less frequently. Herein, we report a unique visible-light-mediated amidyl radicals synthesis β-amido ketone derivatives. Single-electron (SET) to

Language: Английский

Benzylic C(sp3)–H/C(sp3)–H Coupling with 2-Azaallyl Anions through Single-Electron Transfer and 1,5-Hydrogen Atom Transfer DOI
Dongxiang Liu, Bijun Wang,

Cuirong Qin

et al.

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

Published: March 19, 2025

Herein is reported a novel transition-metal-free intermolecular C(sp3)–H/C(sp3)–H coupling of N-tert-butyl arylamides with N-benzyl imines through single-electron transfer (SET) and 1,5-hydrogen atom (1,5-HAT) strategies. 2-Azaallyl anions as super-electron-donors (SEDs) undergo SET to generate 2-azaallyl radicals amidyl radicals. The radical undergoes 1,5-HAT process form C-centered radical, which subsequently coupled new C–C bonds. This method avoids the use transition metals photoredox catalysts good functional group tolerance yields (29 examples, 87% yield). Radical clock trapping experiments provide significant evidence for

Language: Английский

Citations

0
Discovery and cytotoxic activity of N-CF3-containing pyrroloindolines DOI

Qigang Sun,

Jun‐Yunzi Wu,

Yu Zhang

et al.

Research Square (Research Square), Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Abstract Pyrroloindoline scaffolds are widely found in numerous biologically active and medicinally significant natural products. Meanwhile, the potential applications of N-CF3 compounds medicinal chemistry have garnered increasing attention due to their unique properties. However, pharmacological activities therapeutic N-CF3-containing pyrroloindolines remain underexplored. Building on our previously developed method for constructing pyrroloindoline scaffolds, this study systematically evaluated antitumor a diverse series N-CF₃-containing derivatives. Cell-based assays demonstrated that these derivatives exhibited antiproliferative against human cancer cell lines, including 786-O, A498, HepG2. Further investigations revealed not only induce apoptosis cells but also inhibit colony formation. Moreover, they showed suppress metastasis proliferation, primarily by inducing cycle arrest. These findings suggest hold great promise as anticancer agents merit further development.

Language: Английский

Citations

0
Recent Advances in Radical Coupling Strategies Enabled by 2‐Azaallyl Anions as Super‐Electron‐Donors DOI
Dong Zou, Wei Wang, Jie Ying

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(7), P. 1450 - 1466

Published: Feb. 14, 2024

Abstract Due to amine derivatives widely existing in numerous clinical medicines and bioactive compounds, their synthesis has received considerable attention over the past few decades. Traditional methods for of largely relied on reduction nitroarenes, amides, hydrazines, nitriles, azides. Recently, discovery 2‐azaallyl anions as super‐electron‐donors (SEDs) opened up new possibilities construction diverse carbon‐carbon carbon‐heteroatom bonds through radical coupling strategies. This breakthrough highlights potential generating radicals versatile intermediates organic synthesis. Then, hydrolysis product can easily separate corresponding derivatives. Thus, tremendous been paid C−H functionalization ketimines an alternative strategy Herein, we comprehensively summarize recent progress strategies enabled by SEDs. Their proposed mechanistic pathways, advantages, limitations are also discussed detail. 1. Introduction 2. C−C Bond Formation 2.1. Vinylation Ketimines 2.2. Arylation 2.3. Alkylation 2.3.1. Methylation 2.3.2. Other 3. C−X 3.1. C−P C−S Bonds 3.2. C−N C−O 4. Conclusions

Language: Английский

Citations

3
Sulfenylnitrene-Mediated Nitrogen-Atom Insertion into Pyrroles, Indoles, and Imidazoles DOI Creative Commons
Bidhan Ghosh,

Prakash Kafle,

Rishav Mukherjee

et al.

Published: Feb. 12, 2024

In this study, we harness the distinct reactivity of sulfenylnitrenes, which insert a single nitrogen atom to transform readily available pyrroles, indoles, and imidazoles into synthetically challenging pyrimidines, quinazolines, triazines, respectively. Our additive-free method for skeletal editing employs easily accessible, benchtop-stable sulfenylnitrene precursors as source atom. This chemical approach is compatible with free diverse functional groups, including oxidation-sensitive functionalities like phenol thioether. Additionally, facilitates selective incorporation various natural products, amino acids, pharmaceuticals. Furthermore, have conducted mechanistic studies explored regioselectivity outcomes through DFT calculations.

Language: Английский

Citations

2
Synthesis of indolyl pyrroloindolines via a cascade arylation/cyclization of indole acetamides with 3-substituted indoles DOI
Wei Zhang, Shuai Han, Siyi Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5167 - 5171

Published: Jan. 1, 2024

A novel TEA-mediated cascade arylation/cyclization reaction between indole acetamides and 3-substituted indoles for the synthesis of various indolyl pyrroloindolines has been developed.

Language: Английский

Citations

1
Recent Progress on Organic Electron Donors (OEDs) Enabled Radical Reactions DOI Open Access
Yu Shao, Xiaodong Jia

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 21, 2024

Abstract Over the past few decades, organic transformations facilitated by small molecules have witnessed considerable advancements. Small been widely applied to construction of various skeletons. However, reduction as one fundamental reactions is generally initiated metal‐containing reducing agents, although initial progress electron donors (OEDs) enabled reductive cleavage some chemical bonds had achieved in 1990s. Due their structural diversity and tunability, OEDs can overcome limitations metal‐based such low selectivity poor functional group tolerance well environmental problems caused substantial inorganic waste after reactions. Building on a brief historical overview OED research, this review focuses rencent advancements promoted radical It covers C−X (X=C, O, N etc.) single bonds, cyclization, intermolecular addition unsaturated coupling, functionalization aromatics, C−H bond activation. Additionally, mechanistic insights typical are highlighted for understanding reaction mode involving OEDs.

Language: Английский

Citations

0
Visible-light-driven Net-1,2-Hydrogen Atom Transfer of Amidyl Radicals to Access β-Amido Ketone Derivatives DOI Creative Commons
Yonggang Jiang, Hui Li,

H. Tang

et al.

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

Published: Dec. 3, 2024

Hydrogen atom transfer (HAT) processes provide an important strategy for selective C-H functionalization. Compared with the popularity of 1,5-HAT processes, however, net-1,2-HAT reactions have been reported less frequently. Herein, we report a unique visible-light-mediated amidyl radicals synthesis β-amido ketone derivatives. Single-electron (SET) to

Language: Английский

Citations

0