Advances in trifluoromethylation of C(sp3)-H bonds

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15640%2F25%3A73631320" target="_blank" >RIV/61989592:15640/25:73631320 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61989100:27640/25:10257950

Výsledek na webu

<a href="https://www.sciencedirect.com/science/article/pii/S0010854525004552?via%3Dihub" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0010854525004552?via%3Dihub</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.ccr.2025.216885" target="_blank" >10.1016/j.ccr.2025.216885</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Advances in trifluoromethylation of C(sp3)-H bonds

Popis výsledku v původním jazyce

The trifluoromethyl (-CF3) group is one of the most prevailing functionalities in organic molecules, agrochemicals, and pharmaceuticals that play vital roles in life science applications as well as material technologies. This fluorine-based motif constitutes an integral part of many bioactive compounds and finds noticeable applications in pharmacokinetics, potency, bioavailability, metabolic stability, and membrane permeability. The great diversity of this organofluorine unit and its biological relevance have stimulated chemists in both academic research and industry to develop potential synthetic tactics for the formulation of trifluoromethylated compounds. As a result, several approaches have been well-established for synthesizing CF3-based molecules, including many drugs, insecticides, herbicides, fungicides, and fluoro-polymeric materials. Among these, C-H trifluoromethylation is a preferred approach due to its atom-economical nature and omnipresence of C-H bonds. Several innovative carbon-hydrogen (C-H) functionalization techniques with specific emphasis on C(sp3)-H bond activation to access diverse trifluoromethylated scaffolds have been successfully developed. This review aims to provide insights into the significant advancements in the creation of trifluoromethylated analogs from diverse organic compounds. It highlights the functionalization of various types of relatively inert C(sp3)-H bonds, including C(sp3)-H bond adjacent to carbonyl group, alpha-heteroatom C(sp3)-H bond, benzylic C(sp3)-H bond, alkyl C(sp3)-H bond, and strained C(sp3)-H bond of cycloalkane, achieved through diverse methodologies such as metal catalysis, light-induced approaches, organocatalysis, and metal-free reactions. The plausible mechanisms using experimental and computational methods that govern these reactions are also discussed. Future trends and prospects, as well as advancements required for this trifluoromethyl chemistry, are presented. Certainly, this review will be helpful to organic synthetic chemists, particularly to those who are working with fluorinated compounds and life science molecules, as this will undoubtedly inspire and motivate them to contribute more to this specific field of research.

Název v anglickém jazyce

Advances in trifluoromethylation of C(sp3)-H bonds

Popis výsledku anglicky

The trifluoromethyl (-CF3) group is one of the most prevailing functionalities in organic molecules, agrochemicals, and pharmaceuticals that play vital roles in life science applications as well as material technologies. This fluorine-based motif constitutes an integral part of many bioactive compounds and finds noticeable applications in pharmacokinetics, potency, bioavailability, metabolic stability, and membrane permeability. The great diversity of this organofluorine unit and its biological relevance have stimulated chemists in both academic research and industry to develop potential synthetic tactics for the formulation of trifluoromethylated compounds. As a result, several approaches have been well-established for synthesizing CF3-based molecules, including many drugs, insecticides, herbicides, fungicides, and fluoro-polymeric materials. Among these, C-H trifluoromethylation is a preferred approach due to its atom-economical nature and omnipresence of C-H bonds. Several innovative carbon-hydrogen (C-H) functionalization techniques with specific emphasis on C(sp3)-H bond activation to access diverse trifluoromethylated scaffolds have been successfully developed. This review aims to provide insights into the significant advancements in the creation of trifluoromethylated analogs from diverse organic compounds. It highlights the functionalization of various types of relatively inert C(sp3)-H bonds, including C(sp3)-H bond adjacent to carbonyl group, alpha-heteroatom C(sp3)-H bond, benzylic C(sp3)-H bond, alkyl C(sp3)-H bond, and strained C(sp3)-H bond of cycloalkane, achieved through diverse methodologies such as metal catalysis, light-induced approaches, organocatalysis, and metal-free reactions. The plausible mechanisms using experimental and computational methods that govern these reactions are also discussed. Future trends and prospects, as well as advancements required for this trifluoromethyl chemistry, are presented. Certainly, this review will be helpful to organic synthetic chemists, particularly to those who are working with fluorinated compounds and life science molecules, as this will undoubtedly inspire and motivate them to contribute more to this specific field of research.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/EH22_008%2F0004587" target="_blank" >EH22_008/0004587: Technologie za hranicí nanosvěta</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Coordination Chemistry Reviews

ISSN

0010-8545

e-ISSN

1873-3840

Svazek periodika

542

Číslo periodika v rámci svazku

November

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

28

Strana od-do

nestránkováno

Kód UT WoS článku

001517168700001

EID výsledku v databázi Scopus

2-s2.0-105008353202