Photoinduced Aromatization-Driven Deconstructive Fluorosulfonylation of Spiro Dihydroquinazolinones DOI

Wenpeng Yang,

Hong-Jie Miao,

Gang Wang

et al.

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

Published: Nov. 30, 2024

A catalyst-free photoinduced deconstructive fluorosulfonylation cascade of spiro dihydroquinazolinones with DABSO and NFSI is reported. This protocol features mild reaction conditions, good yields excellent functional group tolerance, providing a practical approach to the quinazolin-4(1H)-one-functionalized aliphatic sulfonyl fluorides. In addition, ease gram-scale synthesis versatility SuFEx exchange highlight application potential this protocol.

Language: Английский

Direct electrochemical synthesis of arenesulfonyl fluorides from nitroarenes: a dramatic ionic liquid effect DOI
Xianqiang Kong, Qianwen Liu, Yiyi Chen

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(6), P. 3435 - 3440

Published: Jan. 1, 2024

A practical electrosynthesis of aryl sulfonyl fluorides from nitroarenes is described. Cheap N -methylimidazolium p -toluenesulfonate has been found to be an effective additive, promoting the desired fluorosulfonylation under very mild conditions.

Language: Английский

Citations

24

Recent Advances in Developing Radical Methods for the Synthesis of Aliphatic Sulfonyl Fluorides DOI

Lu Lin,

Guanhua Pei,

Zhong‐Yan Cao

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(23)

Published: May 25, 2024

Abstract Sulfonyl fluorides have widespread applications in many fields, including organic synthesis, chemical biology, drug discovery and materials science. In particular, the past decade, a number of aliphatic sulfonyl been identified showing various biological activities. These appealing features brought about significant advancement developing synthetic methods to access fluorides. this review, we will discuss recent developments radical approaches for synthesis

Language: Английский

Citations

11

Visible-Light-Mediated Three-Component Strategy for the Synthesis of Isoxazolines and Isoxazoles DOI
Yanchuan Li, Yu Zhang, Jinxin Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3130 - 3134

Published: April 8, 2024

Isoxazolines and isoxazoles commonly serve as core structures of many therapeutic agents natural products. However, the metal-free catalysis-free strategy for synthesis these privileged motifs at room temperature remains a challenging task. Herein, we report three-component to afford diverse isoxazolines via [3 + 2] cycloadditions in situ-formed nitronates olefins/alkynes under visible-light irradiation.

Language: Английский

Citations

8

Development of a biphasic catalytic system for Ullmann coupling hydroxylation of 2,6-dichlorotoluene DOI
Long Zhang,

Yuran Cheng,

G XU

et al.

Surfaces and Interfaces, Journal Year: 2025, Volume and Issue: unknown, P. 106382 - 106382

Published: April 1, 2025

Language: Английский

Citations

0

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

0

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

2

Recent progress in sulfonyl fluoride synthesis via the radical sulfur dioxide insertion and fluorination strategy DOI

Haozhen Zhang,

Wangchuan Xiao,

Fanhong Wu

et al.

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

Published: Oct. 8, 2024

Language: Английский

Citations

2

Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent DOI
Huihui Yang, Miaomiao Li, Aijun Zhang

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110425 - 110425

Published: Oct. 1, 2024

Language: Английский

Citations

2

On the Existence and Relevance of Copper(III) Fluorides in Oxidative Trifluoromethylation DOI
Noel Nebra, Daniel Joven‐Sancho

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: June 24, 2024

Abstract Numerous reports invoke CuIII–F intermediates engaging in oxidative cross-couplings mediated by low/mid-valent copper and formal sources of ‘F+’ oxidants. These elusive typically instable CuIII fluorides have been rarely characterized or spectroscopically identified, making their existence participation within catalytic cycles somehow questionable. We authenticated a stable organocopper(III) fluoride that undergoes Csp–CF3 bond formation upon addition silyl-capped alkynes following 2 e– CuIII/CuI redox shuttle. This finding strongly supports the intermediacy C–C coupling. review herein state art about well-defined enabling cross-coupling reactions. 1 Introduction Brief History Coupling-Competent Fluorides 3 Design an Isolable – yet Reactive Organocopper(III) Fluoride 4 Alkyne Trifluoromethylation: Scope Mechanism 5 Extension to Aryl–CF3 C–Heteroatom Couplings 6 Summary Outlook

Language: Английский

Citations

1

Regio- and enantioselective hydrofluorination of internal alkenes via nickel-catalyzed hydrogen atom transfer DOI
Fan Chen, Xiaoyu Zhao,

Weihang Miao

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: unknown, P. 110239 - 110239

Published: July 1, 2024

Language: Английский

Citations

1