Trifluoroethylation and Pentafluoropropylation of C(sp 3 )-H Bonds.

Autor: Le TV; Department of Chemistry, University of Houston, 3585 Cullen Blvd, Houston, TX, USA., Ramachandru GG; Department of Chemistry, University of Houston, 3585 Cullen Blvd, Houston, TX, USA., Daugulis O; Department of Chemistry, University of Houston, 3585 Cullen Blvd, Houston, TX, USA.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Mar 20; Vol. 30 (17), pp. e202303190. Date of Electronic Publication: 2024 Jan 18.
DOI: 10.1002/chem.202303190
Abstrakt: Polyfluorinated substituents often enhance effectiveness, improve the stability within metabolic processes, and boost the lipophilicity of biologically active compounds. However, methods for their introduction into aliphatic carbon chains remain very limited. A potentially general route to integrate the fluorinated scaffolds into organic molecules involves insertion of fluorine-containing carbenes into C(sp 3 )-H bonds. The electron-withdrawing characteristics of perfluoroalkyl groups enhances the reactivity of these carbenes which should enable the functionalization of unactivated C(sp 3 )-H bonds. Curiously, it appears that use of perfluoroalkyl-containing carbenes in alkane C-H functionalization is exceedingly rare. This concept describes photolysis, enzymatic catalysis, and transition metal catalysis as three primary approaches to C(sp 3 )-H functionalization by trifluoromethylcarbene and its homologues.
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Databáze: MEDLINE
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