Recent Progress on Methods for the Preparation of Mono/Di/Trifluoromethoxylation Reagents DOI
Wei Zheng,

Fengzheng Liu,

Hongqiong Zhao

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(11), P. 3321 - 3321

Published: Jan. 1, 2024

Language: Английский

Recent Advances in Cyclization Reactions of 1,6‐Enynes DOI

J.H. Liu,

Sheng‐Qi Xu,

Yaping Han

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(6), P. 1220 - 1268

Published: Jan. 22, 2024

Abstract Elaborated molecular architectures, specifically those bearing one or more carbon stereocenters, stand as an important class of carbocyclic and heterocyclic frameworks because they are frequently occurring core structures in numerous natural products biologically active pharmaceutical molecules. Over the past few decades, development versatile synthetic approaches via cascade cyclization reactions 1,6‐enynes for construction a series fused spiro compounds has been focus great deal research initiatives. These synthesis strategies peculiarly fascinating context assembly wide array molecules, products, agrochemicals, functional materials. In this review, recent developments transformations with diverse coupling reagents summarized since 2018, which could be divided into five categories: 1) Introduction; 2) Transition metal catalyzed 1,6‐enynes; 3) Metal‐free 4) Visible‐light‐induced 5) Electrocatalytic 1,6‐enynes.

Language: Английский

Citations

13

N-monofluoromethoxy benzoimidazole: a bench stable reagent for direct radical monofluoromethoxylation of alkenes DOI
Ning Chen, Jingjing Ling, Keguang Cheng

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 12, 2025

Language: Английский

Citations

1

2,2‐Difluoroethylation of Heteroatom Nucleophiles via a Hypervalent Iodine Strategy DOI Creative Commons
Suman Das,

Charlotte McIvor,

Andrew Greener

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 8, 2024

The 2,2-difluoroethyl group is an important lipophilic hydrogen bond donor in medicinal chemistry, but its incorporation into small molecules often challenging. Herein, we demonstrate electrophilic 2,2-difluoroethylation of thiol, amine and alcohol nucleophiles with a hypervalent iodine reagent, (2,2-difluoro-ethyl)(aryl)iodonium triflate, via proposed ligand coupling mechanism. This transformation offers complementary strategy to existing methods allows access wide range 2,2-difluoroethylated nucleophiles, including the drugs Captopril, Normorphine Mefloquine.

Language: Английский

Citations

5

Fluoroalkoxylating Reagents in Organic Synthesis: Recent Advances DOI
Mingxi Chen, Quande Wang

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(25)

Published: April 22, 2024

Abstract The fluoroalkoxy groups (OR f ) are widely used motifs in pharmaceutical and agrochemical fields due to their unique physicochemical properties including higher lipophilicity increased metabolic stability. Thus, the high value of OR ‐containing derivatives has stimulated development fluoroalkoxylation reactions. In this review, we highlight recent progress various trifluoroalkoxylating reagents applications organic synthesis past five years.

Language: Английский

Citations

4

Radical trifluoromethoxylation of fluorinated alkenes for accessing difluoro(trifluoromethoxy)methyl groups DOI Creative Commons

Koki Kawai,

Mai Usui,

Sota Ikawa

et al.

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

Published: Jan. 1, 2025

In this study, we explore the potential of difluoro(trifluoromethoxy)methyl group, CF 2 –O–CF 3 , an underexplored but promising structural analog trifluoromethoxy group (OCF ).

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

Photoredox Catalysis DOI
Geraint H. M. Davies, Patricia Z. Musacchio, Trevor C. Sherwood

et al.

Elsevier eBooks, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0

N-Trifluoroethoxy Benzotriazolium Triflate: A Readily Available Reagent for Direct Radical Trifluoroethoxylation of Alkenes DOI
Mingxi Chen, Yu Lu, Yiwen Shen

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9586 - 9591

Published: Oct. 29, 2024

Herein, we describe the development and application of a novel benzotriazole-based reagent toward radical trifluoroethoxylation. Various alkene classes, including styrene derivatives, enol carbonates, allyl silanes, are viable reaction partners in this transformation, yielding diverse trifluoroethoxylated products. Furthermore, method is readily applicable for late-stage modification natural product drugs molecules. Mechanistic computational studies suggest intermediacy an OCH2CF3 generated under photocatalytic conditions.

Language: Английский

Citations

3

Photocatalytic C–H Trifluoroethoxylation of (Hetero)arenes DOI
Mingxi Chen, Jingjing Ling, Keguang Cheng

et al.

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

Published: Feb. 20, 2025

The trifluoroethoxy group (OCH2CF3) is a valuable motif prevalent in pharmaceuticals and agrichemicals. Herein, we present simple radical trifluoroethoxylation method that enables nondirected functionalization of C-H bonds broad array substrates, providing access to (hetero)aryl trifluoroethyl ethers. current protocol tolerates variety synthetically pharmacologically relevant functional groups. Applicability also demonstrated through the late-stage biorelevant molecules marketing drugs.

Language: Английский

Citations

0

Visible light-promoted oxycarbonylation of unactivated alkenes DOI Creative Commons

Hefei Yang,

Yuanrui Wang,

Le‐Cheng Wang

et al.

EES Catalysis, Journal Year: 2024, Volume and Issue: 2(6), P. 1247 - 1252

Published: Jan. 1, 2024

We developed an intermolecular oxygen-centered radical addition carbonylation reaction of unactivated alkenes under visible light irradiation which provides a new strategy to alkenes.

Language: Английский

Citations

2