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
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01519