Photoswitchable Regiodivergent Azidation of Olefins with Sulfonium Iodate(I) Reagent
Dodla S Rao1, Thurpu R Reddy1, Aakanksha Gurawa1
1Carbohydrate Chemistry Research Laboratory (CCRL), Department of Chemistry , Malaviya National Institute of Technology (MNIT) , Jaipur 302017 , India.
Abstract:
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 π bond 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.
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