Abstract
Recent progress in the trifluoromethylation of alkenes with Togni's reagents is reviewed. Seven approaches to the trifluoromethylation of alkenes are summarized: (i) oxytrifluoromethylation, (ii) aminotrifluoromethylation, (iii) allylic trifluoromethylation, (iv) cyanotrifluoromethylation, (v) trifluoromethylazidation, (vi) carbotrifluoromethylation, and (vii) trifluoromethylation- rearrangement.
Highlights
Togni and co-workers[10] reported a conceptually new family of formally electrophilic CF3 transfer reagents based on a cyclic hypervalent iodine(III) core, the most successful ones being Togni’s reagents 1 and 2 (Scheme 1)
These reagents are employed in the trifluoromethylation of phosphorus, carbon- and oxygen-centered nucleophiles such as phosphines,[11] α-nitro- and β-keto-esters,[12,13] phosphorothioates,[14] aromatics,[15] alcohols,[16] sulfonic acids,[17] hydrogen phosphates,[18] aldehydes,[19] phenols,[20] arylboronic acids,[21] and quinones[22]
This review provides an overview of trifluoromethylation of alkenes with Togni’s reagents over the period from 2011 to the present
Summary
CAUTION! Togni’s reagents were reported to be explosive, and should only be handled with the appropriate knowledge and safety measures.[31]. Togni’s reagents were reported to be explosive, and should only be handled with the appropriate knowledge and safety measures.[31] Togni’s reagent 1, which showed a decomposition energy of 502 J/g in the DSC-measurement, is dangerously explosive and may only be transported by approval of the national competent authority. Another critical property of Togni’s reagent 1 is the fast combustion when ignited. Togni’s reagent 2 produces a melting signal with an onset at 77 °C followed by a decomposition with a strong exotherm of 790 J/g with an onset at 135 °C and a maximum heat flow of 6 W/g in an aluminum pan with pierced lid.[31]
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
