ol7b02844_si_002.cif (12.71 kB)
Photocatalytic Generation of Nitrenes for Rapid Diaziridination
dataset
posted on 2017-10-21, 00:00 authored by Ramij
R. Mondal, Saikat Khamarui, Dilip K. MaitiA blue LED, an organic photocatalyst
(rose bengal), and the Lewis
acid like oxidant PhI(OAc)2 were utilized to generate nitrene
intermediates through reactions of 1,2-diols and aliphatic amines
under mild reaction conditions. A versatile and rapid diaziridination
strategy was established to construct functionalized 1,2-disubstituted
diaziridines, diaziridines with chiral substituents, and 1,2,3-trisubstituted
analogues with excellent reaction rates, yields, and stereoselectivities.
Control and labeling experiments to elucidate the mechanism of this
elegant metal-free photocatalyzed cyclization reaction were performed.