Controlling the Reactivity of IBA-N3 by Switching Halogen Salts: Providing a Universal Strategy for Haloazidation of Alkenes
Chen-Xi Xia
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorXin-Lei Sun
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorJinfeng Zhang
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorYue Ren
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorYan Yu
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorKuai Wang
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorCorresponding Author
Ling-Guo Meng
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
E-mail: [email protected]Search for more papers by this authorChen-Xi Xia
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorXin-Lei Sun
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorJinfeng Zhang
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorYue Ren
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorYan Yu
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorKuai Wang
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
Search for more papers by this authorCorresponding Author
Ling-Guo Meng
Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education; School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui, 235000 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
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 (XN3), 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-N3 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-N3 via switching halogen salts, different intermediates can be controllably produced to achieve regioselectivity and chemoselectivity in the haloazidation of alkenes.
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