1449417-93-9Relevant academic research and scientific papers
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.
Stereoselective radical azidooxygenation of alkenes
Zhang, Bo,Studer, Armido
, p. 4548 - 4551 (2013/09/24)
Radical azidooxygenation of various alkenes is described. A readily prepared N3-iodine(III) reagent acts as a clean N3-radical precursor. Radical generation is achieved with TEMPONa acting as a mild organic reducing reagent. The C-radical generated after N3-radical addition is efficiently trapped by in situ generated TEMPO. Yields are good to excellent, and for cyclic systems azidooxygenation occurs with excellent diastereoselectivity.
