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Zinc‐Catalysed N ‐Iodosuccinimide‐Enabled Selective N 2 ‐Olefination of Benzotriazoles with Alkenes
Author(s) -
Zhu LiLi,
Tian Lifang,
Zhang Hui,
Xiao Lina,
Luo Wen,
Cai Bin,
Wang Haifeng,
Wang Chunjie,
Liu Guanglu,
Pei Chaoyu,
Wang Yahui
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801303
Subject(s) - chemistry , regioselectivity , stereospecificity , zinc , combinatorial chemistry , selectivity , isomerization , hydrogen bond , organic chemistry , medicinal chemistry , catalysis , molecule
Herein, we describe a zinc‐catalysed N 2 ‐selective olefination of benzotriazoles with unactivated alkenes and styrenes. The transformation is achieved by a N ‐iodosuccinimide (NIS)‐mediated two‐step, one‐pot approach, proceeding through sequential regioselective β ‐iodoalkylation of benzotriazoles with alkenes and a subsequent base‐promoted 1,2‐elimination. The N 2 ‐selective β ‐iodoalkylation of benzotriazoles is highly stereospecific and works under very simple and mild conditions, exhibiting excellent functional group tolerance. The high N 2 ‐selectivity is attributed to intermolecular hydrogen bonding between the N ‐iodosuccinimide and the NH hydrogen bond donor at the 1‐position of the benzotriazoles. This scalable process, serving as an efficient method for modular assembly of structurally diverse N 2 ‐olefinated benzotriazoles, will significantly contribute to the chemistry of N 2 ‐functionization of benzotriazoles.