4098-15-1Relevant articles and documents
A Smooth and Practicable Azido-Iodination Reaction of Alkenes Based on IPy2BF4 and Me3SiN3
Barluenga, Jose,Alvarez-Perez, Monica,Fananas, Francisco J.,Gonzalez, Jose M.
, p. 335 - 337 (2001)
The reaction of alkenes with IPy2BF4 and Me3SiN3 under the influence of BF3 · OEt2 provides a mild an efficient entry to vicinal azidoiodoalkanes. Besides the simplicity of the experimental protocol and the convenience found in the handling of the reagents, the use of stoichiometric amounts of the azide source is remarkable, and overrides the known and always troublesome dependence on large excesses of azide to accomplish this synthetically valuable transformation.
A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach
Andresini, Michael,Degannaro, Leonardo,Luisi, Renzo
supporting information, p. 203 - 209 (2021/02/26)
The reported flow-batch approach enables the easy preparation of 2H-azirines and their stereoselective transformation into highly functionalized NH-aziridines, starting from vinyl azides and organolithium compounds. The protocol has been developed using c
Photoswitchable Regiodivergent Azidation of Olefins with Sulfonium Iodate(I) Reagent
Rao, Dodla S.,Reddy, Thurpu R.,Gurawa, Aakanksha,Kumar, Manoj,Kashyap, Sudhir
supporting information, p. 9990 - 9994 (2019/12/02)
Photoswitchable strategy for selective azidation of structurally diverse olefins under transition-metal-free conditions is reported. The unprecedented reactivity of trimethylsulfonium [bis(azido)iodate(I)] species under visible light allows radical azidooxygenation of the C═C πbond with distinctive selectivity. In the absence of visible light, the reaction proceeds through an ionic intermediate which led to complementary regioselectivity to provide α-alkyl azides. Mechanistic studies reveal that light-controlled regiodivergent azidation involving radical or an ionic pathway can be accomplished with exclusive regioselectivity.
Photoredox-catalysed redox-neutral trifluoromethylation of vinyl azides for the synthesis of α-trifluoromethylated ketones
Qin, Hai-Tao,Wu, Shu-Wei,Liu, Jia-Li,Liu, Feng
supporting information, p. 1696 - 1699 (2017/02/10)
A redox-neutral, mild, and simple protocol is developed for the synthesis of α-trifluoromethylated ketones from vinyl azides under transition-metal-free conditions. In the presence of organic photoredox catalyst N-methyl-9-mesityl acridinium and sodium trifluoromethanesulfinate, a broad range of substituted vinyl azides were found to react smoothly upon visible-light irradiation, readily furnishing the corresponding products in satisfied yields.