Controlling the Reactivity of IBA-N3 by Switching Halogen Salts: Providing a Universal Strategy for Haloazidation of Alkenes
Chen-Xi Xia , Xin-Lei Sun , Jinfeng Zhang , Yue Ren , Yan Yu , Kuai Wang , Ling-Guo Meng
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (16) : 1839 -1845.
Controlling the Reactivity of IBA-N3 by Switching Halogen Salts: Providing a Universal Strategy for Haloazidation of Alkenes
Although various routes have been reported for haloazidation, unavoidable problems exist, such as environmentally unfriendly monomer halogen, the need for in situ generation of unstable halogen azides (XN 3), applicability to one type of haloazidation and inability to precisely control selectivity. Herein, we developed a universal strategy for haloazidation of alkenes through controlling the reactivity of IBA-N 3 by switching halogen salts, allowing for the synthesis of a diversity of halogen azide products. Mechanistic studies have shown that by tuning the reactivity of IBA-N 3 via switching halogen salts, different intermediates can be controllably produced to achieve regioselectivity and chemoselectivity in the haloazidation of alkenes.
Haloazidation / Alkene / IBA-N 3 / Halogen salts / Difunctionalization / Selectivity / Radicals / Synthetic methods
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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