10.1002/anie.201802347
Angewandte Chemie International Edition
COMMUNICATION
iodonium species allows the cyclization not only with aliphatic
amines but for aromatic and heteroaromatic amines, which
notoriously withstand cyclization in case of traditional leaving
groups such as halides or sulfonium salts. This finding was
supported by the results of quantum chemical calculations
focusing on the reaction mechanism and the comparison of
reactivity of trifluoropropenyl substrates equipped with different
leaving groups. The enhanced reactivity feature of the novel
iodonium reagent significantly expands the scope and synthetic
utility of the aziridination reaction and could provide access to
various important trifluoromethylated building blocks, and gain
application in further trifluoropropenylation reactions with C and
heteroatom nucleophiles.
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Acknowledgements
This work was supported by National Research, Development
and Innovation Office (Grant No. K116034 and K125020) and by
the János Bolyai Research Scholarship of the Hungarian
Academy of Sciences. The authors thank to Ágnes Gömöry for
the HRMS measurements and László Burai and Tamás Gáti for
the help in the structure determination.
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Keywords: Aziridines • Heterocycles • Iodonium salts • Trifluormethyl group •
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