Recent Advances in C–F Bond Activation of Acyl Fluorides Directed toward Catalytic Transformation by Transition Metals, N-Heterocyclic Carbenes, or Phosphines DOI
Yasushi Nishihara, Tian Tian, Qiang Chen

et al.

Synthesis, Journal Year: 2022, Volume and Issue: 54(17), P. 3667 - 3697

Published: May 6, 2022

Abstract Numerous studies on the activation of carbon–fluorine bonds have been reported in recent years. For example, acyl fluorides utilized as versatile reagents for acylation, arylation, and even fluorination. In this review, we focus compounds with bonds, highlight advances strategies their C–F via transition-metal catalysis, N-heterocyclic carbene (NHCs) organophosphine classical nucleophilic substitution reactions. 1 Introduction 2 Transition-Metal-Mediated Bond Activation 2.1 Acylation (Carbonyl-Retentive) Coupling Reactions 2.2 Decarbonylative 2.3 by Other Transition Metals 3 N-Heterocyclic Carbenes 3.1 NHC-Catalyzed Cycloaddition Acyl Fluorides 3.2 Radical Functionalization 3.3 Nucleophilic Fluorination (Hetero)aromatics 4 Phosphines 4.1 Phosphine-Catalyzed Direct 4.2 Indirect 5 Classical Substitution 6 Miscellaneous Examples 7 Summary Perspective

Language: Английский

Controllable Fluorocarbon Chain Elongation: TMSCF2Br-Enabled Trifluorovinylation and Pentafluorocyclopropylation of Aldehydes DOI
An Liu, Xianghong Zhang, Feng Zhao

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(3), P. 1806 - 1812

Published: Jan. 9, 2024

Controllable fluorocarbon chain elongation (CFCE) is a promising yet underdeveloped strategy for the well-defined synthesis of structurally novel polyfluorinated compounds. Herein, direct and efficient trifluorovinylation pentafluorocyclopropylation aldehydes are described by using TMSCF

Language: Английский

Citations

6
Ring‐Opening Functionalization/Cyclization Reactions of Cycloalkanols under Transition‐Metal‐Free Conditions DOI

Wenjun Han,

Jun‐Long Zhan,

Fang‐Long Yang

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(9)

Published: Feb. 8, 2024

Abstract Cycloalkanols ring‐opening transformation is one of the most valuable and wide area research. Among numerous methods that have been developed, transition‐metal‐free approaches attracted great interest from both chemists pharmacologists. This largely due to advantages being environmentally benign, cost‐effective operationally simple. Here we provide a comprehensive outline on recent advances in synthesis distally substituted ketones cyclic compounds via cycloalkanols under conditions.

Language: Английский

Citations

6
Organo-Photoredox Catalyzed gem-Difluoroallylation of Glycine and Glycine Residue in Peptides DOI

Ruofan Lin,

Yujie Shan,

Yan Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4056 - 4066

Published: March 7, 2024

An organo-photoredox catalyzed gem-difluoroallylation of glycine with α-trifluoromethyl alkenes via direct C(sp3)–H functionalization and C–F bond activation has been described. As a consequence, broad range gem-difluoroalkene-containing unnatural amino acids are afforded in moderate to excellent yields. This reaction exhibits multiple merits such as readily available starting materials, substrate scope, mild conditions. The feasibility this highlighted by the late-stage modification several peptides well improved vitro antifungal activity compound 3v toward Valsa mali compared that commercial azoxystrobin.

Language: Английский

Citations

6
Fluorine-Retentive Strategies for the Functionalization of gem-Difluoroalkenes DOI
Ryan A. Altman, Jacob P. Sorrentino

Synthesis, Journal Year: 2021, Volume and Issue: 53(21), P. 3935 - 3950

Published: July 12, 2021

gem-Difluoroalkenes are readily available fluorinated building blocks, and the fluorine-induced electronic perturbations of alkenes enables a wide array selective functionalization reactions. However, many reactions gem-difluoroalkenes result in net C─F to generate monofluorovinyl products or addition F trifluoromethyl-containing products. In contrast, fluorine-retentive strategies for remain less generally developed, is now becoming rapidly developing area. This review will present development including electrophilic, nucleophilic, radical, transition metal catalytic with an emphasis on key physical organic mechanistic aspects that enable reactivities.

Language: Английский

Citations

36
Recent Advances in C–F Bond Activation of Acyl Fluorides Directed toward Catalytic Transformation by Transition Metals, N-Heterocyclic Carbenes, or Phosphines DOI
Yasushi Nishihara, Tian Tian, Qiang Chen

et al.

Synthesis, Journal Year: 2022, Volume and Issue: 54(17), P. 3667 - 3697

Published: May 6, 2022

Abstract Numerous studies on the activation of carbon–fluorine bonds have been reported in recent years. For example, acyl fluorides utilized as versatile reagents for acylation, arylation, and even fluorination. In this review, we focus compounds with bonds, highlight advances strategies their C–F via transition-metal catalysis, N-heterocyclic carbene (NHCs) organophosphine classical nucleophilic substitution reactions. 1 Introduction 2 Transition-Metal-Mediated Bond Activation 2.1 Acylation (Carbonyl-Retentive) Coupling Reactions 2.2 Decarbonylative 2.3 by Other Transition Metals 3 N-Heterocyclic Carbenes 3.1 NHC-Catalyzed Cycloaddition Acyl Fluorides 3.2 Radical Functionalization 3.3 Nucleophilic Fluorination (Hetero)aromatics 4 Phosphines 4.1 Phosphine-Catalyzed Direct 4.2 Indirect 5 Classical Substitution 6 Miscellaneous Examples 7 Summary Perspective

Language: Английский

Citations

28