N2‑Selective β‑Thioalkylation of Benzotriazoles with Alkenes

N2‑Selective β‑Thioalkylation of Benzotriazoles with Alkenes

Herein, N2-selective β-thioalkylation of benzotriazoles with unactivated alkenes and styrenes is reported. The N2-selective β-thioalkylation of benzotriazoles is highly stereospecific and works under simple and mild conditions, exhibiting excellent functional group tolerance. The high N2-selectivity...

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Veröffentlicht in:Journal of organic chemistry 2022-10, Vol.87 (19), p.12963-12974
Hauptverfasser: Zhu, Li-Li, Tian, Lifang, Sun, Kunhui, Li, Yiwen, Liu, Guanglu, Cai, Bin, Zhang, Hui, Wang, Yahui
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container_end_page 12974
container_issue 19
container_start_page 12963
container_title Journal of organic chemistry
container_volume 87
creator Zhu, Li-Li
Tian, Lifang
Sun, Kunhui
Li, Yiwen
Liu, Guanglu
Cai, Bin
Zhang, Hui
Wang, Yahui
description Herein, N2-selective β-thioalkylation of benzotriazoles with unactivated alkenes and styrenes is reported. The N2-selective β-thioalkylation of benzotriazoles is highly stereospecific and works under simple and mild conditions, exhibiting excellent functional group tolerance. The high N2-selectivity is a consequence of the combination of hydrogen bonding and Lewis acid/base activation, which reverses the N2-position to be favored for alkylation.
doi_str_mv 10.1021/acs.joc.2c01519
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title N2‑Selective β‑Thioalkylation of Benzotriazoles with Alkenes
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