DOI: 10.1002/chem.201300564. Generation of CF<sub>3</sub>‐Containing Epoxides and Aziridines by Visible‐Light‐Driven Trifluoromethylation of Allylic Alcohols and Amines

Generation of CF3‐Containing Epoxides and Aziridines by Visible‐Light‐Driven Trifluoromethylation of Allylic Alcohols and Amines

10.1002/chem.201300564

Crossref journal-article

Wiley

Chemistry – A European Journal (311)

Bibliography

Kim, E., Choi, S., Kim, H., & Cho, E. J. (2013). Generation of CF3âContaining Epoxides and Aziridines by VisibleâLightâDriven Trifluoromethylation of Allylic Alcohols and Amines. Chemistry â A European Journal, 19(20), 6209â6212. Portico.

Authors 4

Eunjin Kim (first)
Sungkyu Choi (additional)
Heejeong Kim (additional)
Eun Jin Cho (additional)

References 59 Referenced 184

T. Yamazaki T. Taguchi I. Ojima in Fluorine in Medicinal Chemistry and Chemical Biology (Ed.: I. Ojima) Wiley‐Blackwell Chichester 2009 p. 3;
10.1126/science.1131943
10.1038/nature10108
For some Pd‐ Cu‐ or Fe‐catalyzed trifluoromethylations of aromatics and alkenes see:
10.1039/b823249k
10.1126/science.1190524
10.1021/jo1023377
10.1002/chem.201002749
10.1039/c1cc10359h
10.1021/ol2005903
10.1021/ol202885w
10.1002/anie.201108267
10.1002/anie.201200140
10.1002/anie.201202624
For some reviews on visible‐light photoredox catalysis see:
10.1002/ange.200904056
10.1002/anie.200904056
10.1038/nchem.687
10.1039/B913880N
10.1002/anie.201200223
For examples of visible‐light‐driven trifluoromethylations see:
10.1038/nature10647
10.1021/ja108560e
10.1016/j.tetlet.2012.02.032
10.1021/ja300798k
10.1002/anie.201205071
10.1021/jo3022346
For some reviews on epoxides and aziridines see:
10.1021/cr020043t
10.1039/B006015L
{'key': 'e_1_2_4_30_2', 'first-page': '6', 'volume': '3', 'author': 'Padwa A.', 'year': '2006', 'journal-title': 'ARKIVOC'} / ARKIVOC by Padwa A. (2006)
L. P. C. Nielsen E. N. Jacobsen in Aziridines and Epoxides in Organic Synthesis (Ed. A. K. Yudin) Wiley‐VCH Weinheim 2006 p. 229. (10.1002/3527607862.ch7)
As an example of applications see papers on fluorine‐containing epoxy resins:
10.1016/j.surfcoat.2003.10.111
10.1295/polymj.PJ2007096
For some syntheses of CF3‐containing epoxides see:
10.1246/cl.1987.521
10.1021/ja305840g
10.1021/jo0485233
For some syntheses of CF3‐containing aziridines see:
10.1021/jo00117a051
10.1016/S0040-4039(03)00854-2
10.1021/ol100768s
10.1021/ol300539e
Previously Buchwald and Zhu provided various CF3‐containing molecules by ring‐opening reactions of a CF3‐containing epoxide see ref. [8b].
A proposed mechanism of the reaction is presented in the Supporting Information.
Data for solvent effects and concentration effects are presented in the Supporting Information.
Aromatic systems can undergo trifluoromethylation through visible‐light photoredox catalysis with an iridium catalyst see ref. [5a].
Acis/transratio of products for each reaction is presented in the Supporting Information.
A kinetic study on the reaction of an allylic amine was performed with gas chromatography. The amount of side products increases with time. See the Supporting Information.
For some examples of the α‐CH oxidation of amines by photoredox catalysis see:
10.1021/ja909145y
10.1021/ol201376v
10.1039/c1cc12907d
10.1002/ange.201102306
10.1002/anie.201102306
10.1021/ol202883v
10.1021/ol302584y

Dates

Type	When
Created	12 years, 5 months ago (March 28, 2013, 1:49 p.m.)
Deposited	1 year, 10 months ago (Oct. 16, 2023, 5:57 a.m.)
Indexed	1 month ago (Aug. 5, 2025, 8:22 a.m.)
Issued	12 years, 5 months ago (March 28, 2013)
Published	12 years, 5 months ago (March 28, 2013)
Published Online	12 years, 5 months ago (March 28, 2013)
Published Print	12 years, 3 months ago (May 10, 2013)

Funders 0

None

BibTeX

@article{Kim_2013, title={Generation of CF3‐Containing Epoxides and Aziridines by Visible‐Light‐Driven Trifluoromethylation of Allylic Alcohols and Amines}, volume={19}, ISSN={1521-3765}, url={http://dx.doi.org/10.1002/chem.201300564}, DOI={10.1002/chem.201300564}, number={20}, journal={Chemistry – A European Journal}, publisher={Wiley}, author={Kim, Eunjin and Choi, Sungkyu and Kim, Heejeong and Cho, Eun Jin}, year={2013}, month=mar, pages={6209–6212} }

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