Cited by Visible-light-driven Net-1,2-Hydrogen Atom Transfer of Amidyl Radicals to Access β-Amido Ketone Derivatives

Organophotoredox-Driven Three-Component Synthesis of β-Trifluoromethyl β-Amino Ketones DOI

Marta Gil‐Ordóñez, Albert Gallego‐Gamo, Pau Sarró

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 30, 2025

In this work, we present a photoredox three-component reaction that enables the synthesis of medicinally relevant β-trifluoromethyl β-amino ketones from N-trifluoroethylhydroxylamine derivative, styrenes and DMSO. Remarkably, fluoromethyl, difluoromethyl pentafluoroethyl analogues are also accessed using same conditions. The mechanistic investigations, including radical trapping experiments, cyclic voltammetry, Stern-Volmer quenching studies isotope labelling experiments support photoinduced radical/polar crossover Kornblum-type oxidation mechanisms. Finally, applicability organic skeletons is showcased by notable derivatization reactions.

Language: Английский

Citations

Nitrogen-Based Organofluorine Functional Molecules: Synthesis and Applications DOI

Shuai Liu, Jun Zhou, Lu Yu

et al.

Chemical Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

Fluorine and nitrogen form a successful partnership in organic synthesis, medicinal chemistry, material sciences. Although fluorine-nitrogen chemistry has long rich history, this field received increasing interest made remarkable progress over the past two decades, driven by recent advancements transition metal organocatalysis photochemistry. This review, emphasizing contributions from 2015 to 2023, aims update state of art synthesis applications nitrogen-based organofluorine functional molecules chemistry. In dedicated sections, we first focus on fluorine-containing reagents organized according type groups attached nitrogen, including N-F, N-RF, N-SRF, N-ORF. review also covers nitrogen-linked building blocks, catalysts, pharmaceuticals, agrochemicals, underlining these components' broad applicability growing importance modern

Language: Английский

Citations

Visible-Light-Driven Tandem Cyclization of o-Hydroxyaryl Enaminones: Access to 3-(α-Arylsulfonamido)trifluoroethyl Chromones DOI

Jinwei Yuan, Qiang Liu,

X. H. Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 22, 2025

A visible-light-driven intermolecular tandem α-amidotrifluoroethylation/cyclization of enaminones using a previously unreported N-trifluoroethylaminopyridinium salt was achieved in the absence transition metal catalysts or bases. Notable features this synthetic method include mild conditions, high selectivity, excellent functional group compatibility, and satisfactory yields. Preliminary mechanistic studies indicate that reaction proceeds via radical pathway, involving an situ generated N-trifluoroethyl radical, followed by 1,2-H shift.

Language: Английский

Citations

Nucleophilic addition of bulk chemicals with imines using N-functionalized hydroxylamine reagents as precursors DOI

Wei Wang, Yuanyuan Peng, Yang Liu

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 2, 2025

C–C and C–X bond forming reactions are essential tools in organic synthesis, constantly revolutionizing human life. Among the key methods for constructing new chemical bonds nucleophilic addition involving imines. However, inherent challenges synthesizing storing imines have stimulated interest designing stable precursors, which generates situ during reaction. This approach offers a promising alternative to traditional strategies holds significant potential future applications. Here we report direct general of with cost-effective feedstocks easily accessible nucleophiles, specifically utilizing N‑functionalized hydroxylamine reagents as bench-stable precursors. methodology streamlines synthesis various products, such amino acid derivatives, through wide range reaction types, including C–C, C–N, C–O, C–S constructions. Mechanistic studies DFT calculations provide insights into plausible mechanism that supports in-situ imine formation. The stimulate precursors can generate Here, authors N functionalized

Language: Английский

Citations

Visible Light-Induced Sequential Nitrogen Insertion and Benzotriazolation of Quinoxaline-2(1H)-ones DOI

Shankhajit Mondal,

Akhilesh Narendra Malode,

Gokul S. Londhe

et al.

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

Published: Feb. 3, 2025

Herein, we report a visible light-mediated sequential reaction involving in situ generation of benzotriazole from benzene-1,2-diamine and tert-butyl nitrite via nitrogen insertion concomitant cross-coupling with quinoxaline-2(1H)-ones C-N bond formation one pot. This protocol uses metal-free mild conditions demonstrated 36 examples ≤80% yield wide functional group tolerance.

Language: Английский

Citations

Photocatalytic C(sp³)‐H gem‐Difluoroallylation and Alkylation with Alkenes via a Base‐Assisted Formal 1,2‐Hydrogen Atom Transfer of Amidyl Radicals DOI

Meifang Tang,

Bingbing Feng,

Yanyang Bao

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(18), P. 2203 - 2210

Published: May 14, 2024

Comprehensive Summary Compared to well‐established 1,5‐HAT of N ‐centered radicals, the synthetic applications 1,2‐HAT process were scarce due high barrier and constrained three‐membered transition state. Here, we have developed a novel C(sp 3 )‐H gem ‐difluoroallylation via base assisted formal amidyl radicals with reductive quenching cycle photocatalyst. This transformation enables efficient formation α‐aminoalkyl showcases good functional group tolerance. Our preliminary mechanistic experiments, along Density Functional Theory (DFT) calculations demonstrate feasibility especially when by base. Furthermore, our method also succeeds in Giese addition electron‐deficient alkenes as well styrene.

Language: Английский

Citations

Photocatalytic Three‐Component α‐Trifluoroalkyl‐β‐heteroarylation of Unactivated Alkenes with Trifluoroacetates DOI

Yang He, Wenlin Wang, Yuanyuan An

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(27)

Published: May 23, 2024

Abstract We herein disclose a direct and practical photocatalytic three‐component α‐trifluoroalkyl‐β‐heteroarylation of various unactivated alkenes with trifluoroacetates quinoxalin‐2(1 H )‐ones. The reaction takes place via photoinduced LMCT process, allowing efficient synthesis variety 3‐fluoroalkylated )‐one derivatives in moderate to excellent yields under mild conditions.

Language: Английский

Citations

Recent advancements in visible-light-induced direct C(3)–H functionalization of quinoxalin-2(1H)-ones DOI

Xin Han,

Yifan Guo, Y. Hu

et al.

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

Published: Dec. 1, 2024

Language: Английский

Citations

Visible-Light-Induced Markovnikov Hydroalkoxylation of α-Trifluoromethyl Alkenes with ortho-Diketones DOI

Qinlin Chen,

Rundong Fan,

Xuliang Deng

et al.

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

Published: Dec. 6, 2024

We report, for the first time, a visible-light-promoted Markovnikov hydroalkoxylation of α-trifluoromethyl alkenes with 1,2-diketones. This transformation proceeded smoothly in presence tertiary amine (Et

Language: Английский

Citations

Visible-light-driven Net-1,2-Hydrogen Atom Transfer of Amidyl Radicals to Access β-Amido Ketone Derivatives DOI

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