Advances in trifluoromethylation of C(sp3)-H bonds
The result's identifiers
Result code in 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>
Alternative codes found
RIV/61989100:27640/25:10257950
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Advances in trifluoromethylation of C(sp3)-H bonds
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/EH22_008%2F0004587" target="_blank" >EH22_008/0004587: Technology Beyond Nanoscale</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Coordination Chemistry Reviews
ISSN
0010-8545
e-ISSN
1873-3840
Volume of the periodical
542
Issue of the periodical within the volume
November
Country of publishing house
NL - THE KINGDOM OF THE NETHERLANDS
Number of pages
28
Pages from-to
nestránkováno
UT code for WoS article
001517168700001
EID of the result in the Scopus database
2-s2.0-105008353202