Photo-Induced Aziridination of Alkenes with <i>N</i>-Sulfonyliminoiodinanes

Abstract

Activation of N-sulfonyliminiodinanes was achieved by photo-irradiation at 375 nm, which enabled the reaction with several alkenes to afford the corresponding aziridines. Mechanistic studies suggested that the reaction would proceed through a stepwise mechanism via radical intermediates rather than through a concerted process.

Synthesis and Properties of ortho-t-BuSO2C6H4-Substituted Iodonium Ylides

“…Crystallographic parameters of the intra-and intermolecular XB interactions in the crystals of iodonium ylides 2e and 2g. Finally, we investigated the reactivity of the synthesized iodonium ylides under photoirradiation conditions (Scheme 2) [9,[24][25][26][27]. When ylide 2a and ten equivalents of Nmethylpyrrole were irradiated at 365 nm, the active methylene group was introduced at the C2 position of N-methylpyrrole in 61% yield (Scheme 2a).…”

“…Unexpectedly, when ylide 2e-g and ten equivalents of N-methylpyrrole were irradiated at 365 nm, the aryl group (2-t-BuSO 2 C 6 H 4 ) of the ylide was exclusively introduced at the C2 position of N-methylpyrrole (Scheme 2b). Finally, we investigated the reactivity of the synthesized iodonium ylides under photoirradiation conditions (Scheme 2) [9,[24][25][26][27]. When ylide 2a and ten equivalents of Nmethylpyrrole were irradiated at 365 nm, the active methylene group was introduced at the C2 position of N-methylpyrrole in 61% yield (Scheme 2a).…”

“…Based on the crystal structures of the synthesized iodonium ylides in combination with natural-bond-order (NBO) analysis, we also estimated the strength of the intra-and intermolecular XBs [12][13][14][15][16][17][18][19][20][21][22][23]. In addition, we investigated the reactivity of these iodonium ylides under photoirradiation [24][25][26][27].…”

Combining visible-light induction and copper catalysis for chemo-selective nitrene transfer for late-stage amination of natural products

“…Recently, metal-free and catalyst-free aziridination of alkenes have emerged as greener alternatives, but only limited approaches are available 62 – 65 . Among them, photo-induced aziridination of alkenes with iminoiodinanes seems to be a promising tool, but high energy ultraviolet (UV)-irradiation was used in this protocol 64 . An ideal approach is to develop visible-light induced selective aziridination of alkenes in the absence of any catalysts.…”

Aza-Rubottom Oxidation: Synthetic Access to Primary α-Aminoketones

“…Realizing that silyl enol ethers are even more electron-rich than fully carbon-substituted olefins, we were curious to see whether they could be aziridinated and in situ converted to the corresponding α-amino ketones without the use of a transition metal catalyst …”